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Film Reviews

The Underrated 90s: Carlito’s Way (1993)

Original trailer.

A Universal Pictures release.

Cast:

Filmmakers:

Directed by Brian De Palma.

Written by David Koepp.

Based on the novels After Hours and Carlito’s Way by Edwin Torres.

Music by Patrick Doyle.

Edited by Bill Pankow & Kristina Boden.

Cinematography by Stephen H. Burum.

Produced by Martin Bregman, Willi Baer, and Michael Bregman.

90s cinema superstar, Al Pacino (L), reunites with his Scarface director, the great Brian De Palma (R), on the set of Carlito’s Way.

“You’re always being criticized by the fashion of the day. And when the fashion changes, everybody forgets about that.”

-Brian De Palma
Brian De Palma (L) directs Al Pacino (R) for the first time on the set of Scarface (1982).
Theatrical poster.
Brian De Palma (L) with Robert De Niro (R) as Al Capone on the set of The Untouchables (1987).
Theatrical poster.
Pacino (L) and De Palma (R), filming one of the club scenes in Carlito’s Way.

Carlito’s Way arrived in theatres on November 12th, 1993 to mostly mixed reviews, calling the film derivative of even its director’s own previous mob pictures, Scarface and The Untouchables.

https://www.rollingstone.com/tv-movies/tv-movie-reviews/carlitos-way-93187/
The NY Times’ film critic, Janet Maslin.

The headline to Janet Maslin’s November 1993 New York Times review criticized De Palma’s film for its “triumph of atmosphere over detail” (whatever that means).

https://www.rollingstone.com/tv-movies/tv-movie-reviews/carlitos-way-93187/
Rolling Stones’ film critic, Peter Travers.

In his contemporaneous Rolling Stone review, Peter Travers trashed Pacino’s “Rican” accent, writing that he “slips into his Southern drawl from Scent of a Woman.” He called the shootouts “derivative,” the pacing “erratic,” and ultimately dismissed the entire enterprise, writing that it went down “smokin’ in the shadow of Scarface.”

https://ew.com/article/1993/11/12/carlitos-way-2/
Entertainment Weekly’s film critic, Owen Gleiberman

Entertainment Weekly’s Owen Gleiberman labelled the film “unsurprising,” “okay entertainment,” and wrote that, “the plot would have worked better as a lean and mean episode of Miami Vice.”

Of course, once again, this site’s favourite film critic, Robert Ebert, could be counted on to have the more clear-eyed view.

https://www.rogerebert.com/reviews/carlitos-way-1993

Ebert awarded the film 3.5 out of 4 possible stars, praising De Palma’s set-pieces, and rightfully recognizing CW as one of the director’s finest pictures.

Siskel & Ebert review Carlito’s Way and other films from Nov 1993.

Discussing it on their wildly popular TV program, Ebert gave CW thumbs up, but his salty partner, Siskel, thumbs down.

Siskel complained, “I had the same kind of objections I had to Scarface, which was that it was about a character that I really wasn’t interested in, because the movie makes his behaviour heroic in a way that I didn’t think it deserved.”

Director Brian De Palma on the set of Carlito’s Way.
Theatrical poster.

On the Making Of featurette that accompanied the 2004 DVD release, screenwriter David Koepp recalled how De Palma predicted, in the lead up to the film’s premiere, that “Pacino, having just won an Oscar, would be criticized; Koepp, having just done Jurassic Park, would “suck”; Penn would be “brilliant” because he had not done anything for a while; and De Palma, having not been forgiven for The Bonfire of the Vanities, would not quite be embraced.[11]

Producer Martin Bregman (L) on the set of Carlito’s Way.

On the DVD’s audio commentary track, producer Martin Bregman, (also Pacino’s then-manager), said he was suprised by the negative reviews upon CW’s initial release, but noted that its reputation has improved over the years.

https://web.archive.org/web/20080330233746/http://www.reverseshot.com/article/carlitos_way

As Matt Zoller Seitz wrote for Reverse Shot: “Within seven years of its release, Cahiers du Cinema named it the best film of the Nineties.”

https://www.cahiersducinema.com/boutique/produit/n542-janvier-2000/
Theatrical poster.
Stills from De Palma (2015).

In Noah Baumbach‘s & Jake Paltrow‘s excellent 2015 De Palma documentary, the legendary filmmaker laments CW‘s initially poor reception.

De Palma directing John Travolta (in his best part), on location for 1981’s Blow Out.
Theatrical poster.

For me, it is De Palma’s best picture, nudging ahead by a nose in a photo-finish horse race with Blow Out (1981), because it has so much heart, such melancholy emotion, such grandiose visual flourish. They don’t make pictures like this anymore. And De Palma may never make another picture again. Period. So, now feels like an appropriate time to look back and reappraise Carlito’s Way.

First edition hardcover.
Edwin Torres’ “about the author” blurb from the back flap of his first novel, After Hours, which introduced the character of Carlito Brigante.

“His books are a brass knuckle to the groin. There isn’t a false note on any page.”

Richard Price, author of Clockers.
First edition hardcover.

De Palma’s film was primarily based on the novel After Hours, and to a lesser degree, its sequel, Carlito’s Way, by judge-turned-novelist, Edwin Torres.

First edition hardcover.
Theatrical poster.
Q&A director, Sidney Lumet.

Torres also penned the novel from which Sidney Lumet adapted his brilliant (and criminally underrated) 1990 cops & lawyers drama, Q&A (one of his best!), starring Nick Nolte, Armand Asante, and Timothy Hutton, and featuring CW’s Luis Guzmán in a key early supporting role.

CW screenwriter, David Koepp, in his office.
Theatrical poster.

Judge Torres’ Carlito Brigante stories were adapted for the screen by prolific nineties screenwriting phenom David Koepp, hot-as-hellfire coming off the unprecedented success of Steven Spielberg’s giant summer dinosaurs-run-amok blockbuster, Jurassic Park (1993).

Fresh from his Best Actor Oscar win for Scent of a Woman the year before, Pacino headlines here as the titular hero, Carlito Brigante. A reformed drug dealer, Carlito chases the promise of a new life in paradise with Gail, his one true love. But when first we meet Carlito, he’s been shot and is hanging on for dear life by a very loose thread. This may, or may not, be the end of Carlito, but it sure isn’t the beginning of his story. And so the film flashes back a few months prior.

Carlito gets his day in court.

An incarcerated Carlito, doing 30 years in Lewisburg, has his case thrown out on a legal technicality. He’s been given a new lease on life, thanks to the work of his somewhat slimy lawyer, and best pal, Davey Kleinfeld (an almost unrecognizable Sean Penn).

As Kleinfeld, Penn is at his smirking, smarmiest best. Few movie stars are as capable of so completely disappearing into a part. Especially in a supporting role, second-billed to a much bigger star.

Penn displays his first Oscar (2004).
Theatrical poster.
And his second, in 2009.
Theatrical poster.

CW is the first significant suggestion of the calibre of work Penn would go on to accomplish throughout the decade. He’s now a five-time Oscar nominee. He has won Best Actor Oscars twice. First for Clint Eastwood’s Mystic River (2003); and again for Gus Van Sant’s Milk (2008).

Penn (L) with Gary Oldman (R) in State of Grace (1990).
Theatrical poster.

After 1990’s superb (and underappreciated) Irish mob drama, State of Grace, at the height of his rising popularity, Penn famously took a three-year break from acting.

Penn steps behind the camera for The Indian Runner.
Theatrical poster.
Sprinsteen’s best record.

During this hiatus, Penn wrote and directed 1991’s devastating family tragedy The Indian Runner, inspired by Bruce Springsteen’s song Highway Patrolman, from his best record, 1982’s Nebraska. After such a prolonged absence from the silver screen, Penn was welcomed back with open arms and singled out for praise for his performance as Davey Kleinfeld, even by those critics who otherwise dismissed Carlito’s Way.

Theatrical poster.
Pacino, “in the dark,” as Scent of a Woman’s blind colonel.
Pacino with his Oscar.

I can’t say I noticed Pacino slipping into his Scent of a Woman drawl, but in the early courtroom sequence, he does seem to have trouble shaking the wild “blind” eyes of Lt. Col. Frank Slade, his character from that earlier picture.

Rather, Pacino’s performance in this scene reminds me of his “You’re out of order!” speech from the late great Norman Jewison’s …And Justice For All (1979). That film is often cited as the beginning of Pacino’s unfortunate penchant for overacting, but is a performance, and a picture, I very much enjoy.

Director Paul Mazursky as the Judge.

Fans of 1970’s New Hollywood will be happy to spot director Paul Mazursky (Blume in Love; An Unmarried Woman) in an effective cameo.

Theatrical poster.
Theatrical poster.

Mazursky plays the judge forced to throw out Carlito’s case because of the federal prosecutor’s use of illegally obtained wiretaps.

Kleinfeld argues Carlito’s case.
The DA, Norwalk, seethes, splendidly.
90s character actor, James Rebhorn.

Norwalk, the overzealous DA with highly questionable methods , is played by one of my favourite 90s character actors, James Rebhorn (Independence Day). Rebhorn appeared in over 100 films and TV shows before he sadly passed away in 2014.

Rebhorn (R), with Pacino (L), in Scent of a Woman (1992).

Having previously shared the screen with Pacino as the antagonistic headmaster in Scent of A Woman (1992), Rebhorn specialized in playing those parts you love to hate.

Theatrical poster.
Rebhorn in David Fincher’s The Game (1997).

He would go on to appear again with Sean Penn in David Fincher’s beguiling puzzle thriller The Game (1997).

Rebhorn (L) with De Niro (C) in Meet The Parents (2000).

He was hilarious playing opposite Ben Stiller and Robert De Niro in 2000’s in-laws-from-hell cringe-comedy, Meet The Parents.

Polish theatrical poster for The Godfather Pt. II (1974).
G.D. Spradlin in Francis Ford Coppola’s The Godfather Pt. II (1974).
Theatrical poster.
Spradlin, reuniting with Coppola for Apocalypse Now (1979).

Two decades earlier, it’s not hard to imagine Rebhorn cast in the parts made famous by another actor-you-love-to-hate: the late great G.D Spradlin (Francis Ford Coppola’s The Godfather Pt. II and Apocalypse Now).

Thanks to Kleinfeld’s efforts (and Norwalk’s misdeeds) Carlito emerges from the courthouse declaring himself a new man: “rehabilitated and reinvigorated.” He vows to leave the crimes of his past in the past. A one-time legend of the streets, Carlito Brigante is a criminal no more. But Norwalk, the DA, will be watching his every move.

Dancing and drinking the night away to celebrate his release, Carlito lays out his plan to his pal, Kleinfeld, and ignores the party girls the lawyer has lined up for the night. As we will soon come to learn, Carlito only has eyes for one woman: his long lost love, Gail. If Carlito can raise $75,000 he can buy into a used car lot in Florida. “You’re gonna sell cars?” an amused and incredulous Kleinfeld asks. “I know a lot about cars,” Carlito says, though his knowledge is most likely limited to how to steal them.

Carlito loves Kleinfeld, and feels he owes the lawyer his life. Considering the fatalistic events of the opening sequence, it is a debt Carlito may just have to pay back in full before the film’s end. Though he doesn’t realize it yet. For someone who always sees the angles, Carlito has a major, Kleinfeld’s-sized blind spot.

Carlito returns to the streets that made him, and finds them unrecognizable. But he hasn’t been forgotten by the old school gangsters who still hold sway over the barrio.

Carlito meets with his old partner, now a neighborhood kingpin, and assures him Carlito doesn’t hold any grudges. He certainly doesn’t resent his old friend’s success. Nor does he expect any compensation for keeping his mouth shut when he was first arrested. Carlito wants no part of his old life. And he’s no threat. He’s retired, going straight.

But, as is the way in these pictures, and as it will be for Carlito, it isn’t so easy to shake the tendrils of the past. To his young cousin, played by John Ortiz (American Gangster; Silver Linings Playbook), Carlito is a legend. He would be doing the errand boy a huge favor if Carlito would accompany him to a routine money drop. It’s no big deal, “these guys are friends,” his cousin says. It would greatly boost his own minor reputation if Carlito would walk in like his backup. Okay, Carlito says, if only to get this over with. Carlito has promised the boy’s mother that he will look after him. And Carlito is not beyond flattery. He tells anyone who will listen that he is a different man now, but Carlito never corrects anyone who remarks on his legacy. Being one of the biggest gangsters to ever walk these neighborhood streets is a matter of pride for Carlito.

And so, Carlito follows his young cousin into a dive bar pool hall to make the drop. But inside, these guys don’t seem like friends at all.

Actor, Rick Aviles.

Rick Aviles plays Quisqueya, the dealer who Carlito’s cousin is bringing the cash to. Aviles‘ face was instantly recognizable to CW‘s audience for two unforgettable, villainous appearances in a pair of 1990’s biggest blockbusters.

Theatrical poster.
Aviles as Willie Lopez in Ghost (1990).
Willie takes his shot.

Aviles‘ is probably best remembered for his portrayal of Willie Lopez, the mugger who shoots Patrick Swayze dead in Ghost. With only a few minutes of screen-time, Aviles was one of the true standouts of Jerry Zucker’s supernatural romance.

Theatrical poster.
A masked Aviles holds a knife to Bridget Fonda‘s throat in a thrilling sequence from Coppola’s The Godfather Pt. III.
Clip from Godfather Pt III.

He was just as memorable, in an even-briefer appearance, in Francis Ford Coppola’s The Godfather Pt III; playing one-half of the deadly duo sent by Joey Zaza (Joe Mantegna) to kill Vincent Mancini (Andy Garcia).

Aviles in a lobby card for Jim Jarmusch’s Memphis anthology Mystery Train (1989).

Aviles’ promising career as one of the decade’s most interesting character actors was tragically cut short. Just two years after the release of Carlito’s Way, the actor sadly passed away from complications due to AIDS. Quisqueya may be his best work.

Almost instantly, Carlito smells something rotten in the state of Denmark. The whole set up feels wrong. De Palma imbues the scene with a creeping sense of dread as Carlito realizes they have walked into a trap.

An old school pro like Carlito isn’t going to simply wait for the other shoe to drop. He quickly formulates a plan. He will distract the goons gathered around the barroom pool table with one of his famous trick shots.

Of course, Carlito isn’t the only one setting up one of his famous trick shots. Pacino’s dialogue sounds like it could be De Palma himself speaking to the audience. The pool hall sequence, one of the most thrilling of the pictures many breathtaking set pieces, is enough, as Carlito promises, to “make you give up your religious beliefs.”

In a blink-and-you’ll-miss-it bit-part, one of the pool-hall hoods is played by charismatic 90s supporting-actor Jon Seda.

Theatrical poster.
Seda (L) with James Marshall in Gladiator (1992).

Seda was heartbreaking in the underrated teen boxing drama Gladiator the year before (the Cuba Gooding, Jr. picture, not Russell Crowe’s Roman epic).

Theatrical poster.
Seda & Bruce Willis in Terry Gilliam’s 12 Monkeys (1995).

He later played a small but memorable supporting part as a fellow time traveller opposite Bruce Willis in Terry Gilliam‘s 1995 sci-fi classic, 12 Monkeys.

Theatrical poster.
Seda, dying and desperate in Michael Cimino’s The Sunchaser (1996).

But his greatest role would have to be as the prison escapee dying of cancer who kidnaps Woody Harrelson in Michael Cimino‘s underseen road movie The Sunchaser (1996).

As Carlito lines up his shot, the shit hits the fan. He knew it would, and, of course, we did, too. But as with all De Palma set-pieces, the pleasure is not in being surprised by what is about to happen. Rather, it is in the skillful way that the director pays that set-up off. It’s all in the details. As De Palma says, “You have to know where everything is.” Once all the balls are meticulously arranged, knocking them into the pockets is the easy part.

Carlito is quick on the attack, but not quick enough to stop his cousin from getting his throat cut.

Co-editor, Kristina Boden.
Co-editor, Bill Pankow.
https://www.filmcomment.com/blog/interview-bill-pankow/
https://share.google/anueHbDWgDBNRquhq

In the immediate aftermath, Carlito blasts away at the room full of killers, in a dizzying display of masterful cross-cutting by De Palma’s editors, Bill Pankow (9-time De Palma collaborator) & Kristina Boden.

Carlito survives the barrage of bullets blasted his way, and takes refuge in the empty washroom.

“You think you’re big time? You’re gonna fucking die BIG TIME!”

-Carlito Brigante
“You hear that? I’m reloaded!”

Emerging from the bathroom, Carlito finds his cousin murdered, and everybody else dead or gone. But there is no time to mourn the dead. Hearing approaching police sirens, Carlito scoops up the cash and hoofs it.

After disposing of the weapon he took off the goons in the pool hall, Carlito pays his lawyer a visit. Slumped on Kleinfeld’s sofa, Carlito is cool as a cucumber. If the shootout in the pool hall has rattled him, he doesn’t show it. He doesn’t even mention it to Kleinfeld. Instead, Carlito says he has checked out the nightclub Kleinfeld has invested in, and thinks it’s a good investment. Kleinfeld needs someone to run it and keep an eye on Sasso, the slippery manager. Sasso has serious gambling debts and he’s been raiding the till to cover them. Kleinfeld offers to front Carlito the $25 grand that Sasso needs to cover the vig, but Carlito declines. With the $30K he netted in the shootout, he can put his own money in. Kleinfeld asks Carlito where he got the money. He was owed by “some people,” he tells his lawyer, from back in the day.

At El Paraiso, the aptly-named club in question, Sasso (a hilarious Jorge Porcel) welcomes Carlito with open arms, but tells his old friend he’s not called Sasso anymore. “Call me Ron,” he tells Carlito. I don ‘t know why I find that so funny, but I do. Carlito and Sasso/Ron, go back a long way, but Carlito doesn’t waste anytime reminiscing. They have business to discuss. And when it comes to business, Carlito doesn’t fuck around.

Waiting outside is Carlioto’s loyal muscle, Pachanga.

Pachanga is one of the few vestiges of Carlito’s past that he doesn’t try to distance himself from. But it’s evident in all of their scenes together that, while Carlito may tell himself he’s not a gangster any more, Pachanga hasn’t gotten the memo. And one can’t help but forgive him for being confused, because there is still plenty of the old Carlito left on display. There is no greater proof of that than in the first appearance of Benny Blanco, from the Bronx (John Leguizamo).

Benny Blanco represents everything Carlito is running from. Blanco may be the future of the streets, but all Carlito can see is the past. Specifically, his own past.

Fans of the picture know that Carlito has just made his first real mistake by dismissing Blanco, but for Carlito, the rising hood is nothing but a distraction. As always, his thoughts drift towards Gail.

Gail is the one thing from Carlito’s past, the one good thing, that he isn’t running from. Losing Gail is his greatest regret, and his longing for her is perhaps what ultimately sets Carlito’s Way apart from all those gangster pictures, De Palma’s own included, that it is so often compared to. Carlito, and by extension, the picture that bears his name, is undeniably romantic. Carlito is a little like Bogart’s Rick from Casablanca. He has loved and lost, and it has left a black hole in him.

Theatrical poster.
The end of a love affair is the beginning of “a beautiful friendship” in perhaps the greatest ending of any picture ever.

But where Bogie made peace with letting Ingrid Bergman go in the end, Carlito is holding onto his love for Gail with everything he’s got. Dreaming of her has sustained him through his incarceration, and all of his dreams for the future are built around her.

A vision of Gail.

But Carlito is forced to watch her from a distance. We will learn how he pushed her away, how he couldn’t bear to face his time inside while wondering what she was doing on the outside, who she was with. It was a selfish mistake, and we see in Pacino’s eyes just how much the mistake has cost him. Stripped of any dialogue to express his melancholy loneliness and his desperate need to re-connect with Gail, Pacino says everything that needs to be said with nothing more than his wounded gaze. It may be my favourite moment in the entire picture. It is truly a movie star moment. It’s pure cinema. You cannot get this feeling from a stage performance. Pacino’s face fills the frame and De Palma milks it for all he’s got, drenching Carlito in moody, torrential rain and blue-soaked light.

Penelope Ann Miller as Gail.

Gail is played with great tenderness and grace by Penelope Anne Miller (Kindergarten Cop).

Miller in The Shadow.
Orson Welles performing the radio-serial, The Shadow.

A beautiful, talented actor, Miller mostly appeared in supporting parts in a few major pictures, like Alec Baldwin’s take on The Shadow (another failed attempt to re-capture the mega-success of Tim Burton’s Batman), the character made famous by the voice of Orson Welles on the radio program of the same name (“Who knows what evil lurks in the hearts of men? The Shadow knows.”).

Miller at the 67th Emmy Awards.

Rare lead performances in smaller pictures, like the comic, would-be star vehicle, The Gun In Betty Lou’s Handbag, unfortunately failed to make Miller the bigger star that she deserved to be.

Pacino doesn’t get enough credit for his appeal as a romantic leading man, something that distinguishes him from Robert De Niro, the actor (and friend) he is most often compared to.

Pfeiffer and Pacino in Frankie and Johnny (1991).

Consider the abundance of charm that buoyed his winning performance opposite his Scarface co-star, Michelle Pfeiffer, in director Gary Marshall’s (Pretty Woman) underseen 1991 film adaptation of the Terrance McNally play, Frankie & Johnny In The Clare de Lune (wisely shortened to just the characters names for the movie).

In her too-few scenes with him, Miller is every bit Pacino’s match. She runs through the gamut of emotions you would expect to feel if you were suddenly approached on the street by the lover who broke your heart after years of no contact.

As Carlito attempts to rekindle the old spark with Gail, Kleinfeld is busy trying to put out fires. Namely, the raging brush fire that is Mr. Taglialucci, the jailed mob boss from whom Kleinfeld has stolen a million dollars, promising to make a bribe on Taglialucci’s behalf, only to keep the pay-off for himself.

Kleinfeld fervently denies stealing from him, but Taglialucci isn’t having any of it. He knows Kleinfeld pocketed the money, so as far as the mob boss is concerned, he’s got a “million dollar credit” with Kleinfeld. The lawyer can either work off the debt by springing Taglialucci out of the joint (he’s paid off one of the guards to get him in the water and all Kleinfeld has to do is pick him up in this boat), or Taglialucci can have his kid Frankie put a bullet in Kleinfeld’s brain and dump his body in the river instead.

https://www.masterclass.com/classes/david-mamet-teaches-dramatic-writing

It’s not much of a choice, but as David Mamet teaches us in his MasterClass, character is not revealed by the choice between right and wrong, but by two wrongs. Everything that Kleinfeld does from here on out will ultimately come to define him.

Promotional advert for HBO’s Boardwalk Empire.
Promotional advert for season two.

He’s a lawyer whose been flirting with being a gangster. But as we learned in Boardwalk Empire, “you can’t be half a gangster.” Kleinfeld is going to have to pick which side of the fence he’s on.

Poor old Davey Kleinfeld emerges from his prison visit with Taglialucci rattled to the point of vomiting. He knows Taglialucci will kill him either way. But looking out over the water, where he is meant to pick Taglialucci up the next day, Kleinfeld seems suddenly inspired. Maybe there’s a way to get out of all of this without winding up as eel food on the bottom of the river after all.

But Taglialucci isn’t Kleinfeld’s only problem. It isn’t only gangsters who want his head, which we learn when his courtroom nemesis, the prosecutor, Norwalk, pays Kleinfeld an ominous visit.

Meanwhile, Carlito is minding the club (and his own business), working towards that $75,000 grand he needs to buy himself a new life in Florida, when he is paid a visit of his own, by an old friend from his drug dealing past.

Played by a pre-Lord of the Rings-fame Viggo Mortensen, who previously starred in Penn’s Indian Runner debut, Lalin, Carlito’s old pal, was always a stand-up guy. But not anymore.

After taking a couple of bullets in the back, poor Lalin is confined to a wheelchair. But things could be worse. The last Carlito was told, Lalin was doing 30 years. But he beat it, he tells an unconvinced Carlito.

Carlito takes his Norwalk problem to Kleinfeld, who assures him that it’s just a fishing expedition. “You’re not dealing, so he can’t have anything on you.” Kleinfeld promises Carlito that he will take care of the DA.

Carlito goes down to 48th & Broadway, to the place where Lalin has seen Gail dance. But when he gets there, it’s not the classy joint Carlito was expecting.

Expecting to see Gail in a legitimate theatrical production, with her clothes on, he’s shocked to find her naked on stage in the kind of place where the regulars are middle aged men who drink themselves silly drooling over the mostly much younger dancers.

Back at the club, Kleinfeld is getting a lie too familiar with the hostess, Steffie. That usually wouldn’t be a problem, as Carlito says, “Good for Dave,” but Steffie “belongs” to Benny Blanco now. “Who?” Carlito asks. “You remember,” the unlucky waiter who Benny sends to fetch Steffie tells him, “Benny Blanco, from the Bronx.”

And though Carlito is ostensibly standing up for his friend and employee, his issue with Benny Blanco runs much deeper. “This guy is you 20 years ago,” Sasso says, pleading with Carlito to be diplomatic. But that is precisely the problem. Carlito hates the man he used to be. That man cost Carlito his freedom and the love of his life. If Benny Blanco from the Bronx is Carlito 20 years ago, then Benny Blanco from The Bronx can fuck right off.

Kleinfeld, feeling brave with Carlito behind him, makes things worse by pulling a piece. It’s the point of no return and now none of these gangsters can back down without losing face, and so Carlito has no choice but to have Benny Blanco from the Bronx taken out back, where we assume he willl have Benny killed.

But Carlito lets Benny go with a warning. He knows it’s a mistake. The old Carlito would never have left such a lethal loose thread hanging? But “I’m not that guy anymore,” he tells us.

Remember me? Benny Blanco, from the Bronx!

Benny Blanco, to Carlito
Carlito sees the light.

The Prequel:

DVD cover art.
Trailer.
Title shot.

12 years after the original, Carlito’s Way: Rise to Power was released direct-to-video in September, 2005, to universally negative reviews.

https://movies.nytimes.com/2005/10/01/movies/01carl.html
b&wAG.jpg
NY Times film critic Anita Gates.

In her brief NY Times review, film critic Anita Gates singled out what she considered to be the film’s sole notable achievement achievement: “It makes Sean Combs (better known, at the moment, as Diddy) unconvincing as a rich man who enjoys power and luxuries.” Faint praise, indeed.

Author’s screen credit.

CW producer, Martin Bregman, owning the rights to both of Torres’ Carlito Brigante novels, developed the prequel from the material unused by Koepp and De Palma in the first picture. But despite Rise to Power’s many shortcomings, and generally negative reputation, Torres’ allegedly* gave the film his ringing endorsement.

*According to Highdefdigest.com

Jay Hernandez as the young Carlito.

Starring Jay Hernandez (Crazy/Beautiful) as the young Carlito, Rise to Power tells the story of the Puerto Rican gangster’s ascent in the underworld, building the legend that Pacino had to live down in De Palma’s film.

Mario Van Peebles, Michael Kelly, and Jay Hernandez in Michael Bregman’s Carlito’s Way: Rise To Power.

Carlito’s rise begins with his incarceration, locked up with a brilliant Harlem numbers man, played by Mario Van Peebles (New Jack City; Posse), and an Italian mobster, played by Michael Kelly (Netflix’s House of Cards remake), which feels like the set up to a joke that never comes (A Puerto Rican, an Italian, and an African-American walk into a bar…). Each of them represents a neighborhood, and a market, the others cannot access, so the trio conspires to transcend the ethnic barriers of their respective hoods and gang affiliations to make their fortunes together, trafficking in the new wave of heroin flooding New York’s streets in the 1970s.

Hernandez (L), Van Peebles (C), and Kelly (R) in Carlito’s Way: Rise To Power.

Without De Palma at the helm, or a writer of Koepp’s calibre penning the script, Rise to Power never approaches the dazzling emotional and aesthetic heights of the original (but really, how many directors can compete with a master stylist on De Palma’s level?). At its best, Rise to Power feels like an extended, feature-length pilot for a Sopranos-like HBO series. At its worst, it feels like what it is, a Direct-To-Video prequel. It’s nowhere near as good as it could have been, considering that it uses the same source material as the first film. But neither is it even remotely close to being the disaster that most DTV franchise pictures are.

Home video release cover art.

These “legacy sequels” often feature interchangeable sub-titles, new characters and stories, with fan-service cameos by familiar faces from the originals.

Home video release cover art.

They are, without exception, pale imitations intended to cash in on the popularity and success of those original films, and they tend to leave a bad taste in the mouth, souring our fond memories of the films they are meant to honour.

Home video release cover art.

How can you make a sequel to Spike Lee’s biggest commercial joint, without Spike Lee?!! It boggles the mind.

Home video release cover art.

The sub-genre is, to borrow the title of an Errol Morris classic: fast, cheap, and out of control.

Home video release cover art.
Home video release cover art.
Home video release cover art.
Home video release cover art.

For irrefutable evidence, consider the partial list of remarkably un-remarkable DTV sequels featured above.

The nadir of National Lampoon?

And of course, let’s not forget about the depressingly diminishing returns of the National Lampoon franchise, which has fallen so far from the highs of Animal House and the first and third Vacation pictures.

DVD cover art.

Universal Pictures, which produced CW, is possibly the worst offender (for the 5 American Pie Presents movies alone!).

Diddy (L) & Hernandez (R).

Although Hernandez is saddled in Carlito II with the unenviable (and impossible) task of matching Pacino, one of the greatest actors of all time, in one of his best parts, he is likeable and engaging enough in the lead role.

Mario Van Peebles

Mario Van Peebles is great as the Harlem numbers man, and some other notable character actors also appear, including The Wire’s Dominick Lombardozi, and Breaking Bad’s Giancarlo Esposito, in minor roles.

Diddy as Hollywood Nicky.
Mr. Untouchable, Nicky Barnes.
Cuba Gooding Jr. as Nicky Barnes in Ridley Scott’s American Gangster (2009).

Even recently disgraced (and currently incarcerated) hip-hop mogul and sexual predator, Sean Combs (aka “Puff Daddy,” aka “Puffy,” aka “P. Diddy,” aka “Diddy”) is decent in his supporting role as Hollywood Nicky, clearly inspired by infamous Harlem gangster, Nicky “Mr. Untouchable” Barnes, played by Cuba Gooding, Jr. in Sir Ridley Scott’s underrated 2009 crime picture, American Gangster.

Luis Guzmán returns!

But the greatest joy for CW fans will be found in the return of Luis Guzmán, who plays a new character, but gives off heavy Pachanga vibes all the same.

DVD cover art.

Ultimately, the problem with Carlito’s Way: Rise to Power, is one that’s been a matter of public discourse of late: nepotism. To adapt & direct the prequel, Bregman hired his son, Michael Bregman, who served as executive producer on the first film. Bregman Jr., who co-produced the preciously mentioned Shadow reboot, had only one other picture to his name at the time, the forgettable Table One (also co-starring Guzman).

Theatrical poster.
Ami Canaan Mann directs Sam Worthington on location for Texas Killing Fields.
Screenwriter Don Ferrarone.

As with Michael Mann engaging his daughter Ami to direct former DEA Special Agent-In-Charge Don Ferrarone’s excellent screenplay for Texas Killing Fields, these 2nd generation filmmakers more often than not, are lacking their famous parents’ chops (Sofia Coppola, being a notable example to the contrary).

Theatrical poster.
Theatrical poster.
Michael Bregman (R) directs Diddy (R), on the set of Carlito’s Way: Rise To Power.

With only one other picture to his name as director, Bregman Jr. is credited as producer, or associate producer, on a dozen other films, including the high of his father’s earlier Pacino film, Sea of Love (1988), and the low of the notorious Eddie Murphy bomb, The Adventures of Pluto Nash (2002). Rise to Power suggests he shouldn’t quit his day job.

Legacy:

Italian DVD cover art.
Original soundtrack album.

Categories
Film Reviews

The Underrated 90s: The Crossing Guard (1995)

Starring Jack Nicholson, David Morse, Anjelica Huston, Robin Wright, Priscilla Barnes, Piper Laurie, John Savage, Kari Wuher, Richard Bradford, Joe Viterelli, David Baerwald, Eileen Ryan, and Leo Penn.

Cinematography by Vilmos Zsigmond.

Edited by Jay Cassidy.

Music by Jack Nitzsche.

Produced by David S. Hamburger.

Written, produced & directed by Sean Penn.

A Miramax release.

Classic trailer.
DVD cover art.

Like all of the greatest actors who distinguished themselves in the golden era of 1970s New Hollywood (Robert De Niro, Al Pacino, Dustin Hoffman, Gene Hackman, etc), by the 1990s, Jack Nicholson was a bonafide movie star with a screen persona well established, polished, and refined over the decades. The distinction between “actor” and “movie star” is not meant to be pejorative. It is meant only to differentiate the roles in which, as younger men, they disappeared into their characters, and those in which, as older men, they were mostly vehicles that delivered what we had come to expect from them.

You can draw a line in the sand in De Niro’s career after Midnight Run (1988).

For Pacino, it’s Sea of Love (1989).

Hoffman, everything post-Rain Man (1988).

And the Gene Hackman of Loose Cannons (1990) was certainly not recognizable as the Popeye Doyle we know and love from both French Connection pictures.

Jack Nicholson as The Joker, times three.

But more than any of his contemporaries, Nicholson entered the 90s as a mega-star thanks to a little man-in-a-rubber-suit-picture you may, or may not, have heard of:

That isn’t to say that these movie stars never showed up as “actors” again. For each of them, it was mostly in supporting parts that they were able to continue the kind of character work they did in the 70s, and occasionally, they would still get lead role roles (usually in much more modestly budgeted pictures) that showed, not only that they still had it, but that “it” had matured, and ripened with age.

De Niro would have a Night and the City (1992), Mad Dog & Glory (1993), or a Copland (1997), for every Meet The Parents (2000), or Meet The Fockers (2004), or Little Fockers (2010) or Little Fockers (2010)

Pacino would use his Best Actor Oscar-clout from Scent of a Woman (1992) to direct and star in the celebrity-packed Looking for Richard (1996), his actors-putting-on-Shakespeare passion project, in between major studio releases, Heat (1995), and City Hall (1996).

Hoffman would star in small art-house fare like the adaptation of David Mamet’s American Buffalo (1996), and Barry Levinson’s political satire Wag The Dog (1997), also written by Mamet, in between pure genre excercises like Wolfgang Peterson’s prescient killler-virus thriller, Outbreak (1996), and Levinson’s Solaris-lite sci-fi mindfuck, Sphere (1998).

Hackman would use the movie star cred he earned from blockbuster box office hits like Tony Scott’s Crimson Tide (1995) and Enemy of the State (1998), to fuel Mamet’s Heist (2001), and did some of his best work ever in Wes Anderson’s third (and my favourite) feature, The Royal Tennenbaums (2001).

For my money, Nicholson’s best performance in the 90s, and my favourite of his from any era, a role which only Jack could have played, belongs to Sean Penn’s 1995 revenge-and-forgiveness drama, The Crossing Guard.

TCG was Penn’s second feature as writer-director, showing that his first, the searing, tragic family drama, The Indian Runner (1991), was no one-time fluke. With only two pictures under his director’s belt, Penn established himself as a genuine auteur, and one of the best American filmmakers of the decade.

Watch the video for Highway Patrolman on YouTube.

The story of the troubled relationship between two brothers (David Morse and Viggo Mortenson) on opposite sides of the law, Indian Runner was inspired by the lyrics to Bruce Springsteen’s Highway Patrolman from his Nebraska record (1982).

In an act of artistic reciprocity, The Boss would go on to pen the opening credits song, Missing, for The Crossing Guard.

Listen to Missing on YouTube.

Woke up this morning. There was a chill in the air.

Went to the kitchen. My cigarettes were lying there.

Jacket hung on the chair the way I left it last night.

Everything was in place. Everything seemed all right.

…But you were missing.

Missing.

Last night I dreamed, the sky went black.

You were drifting down. Couldn’t get back.

Lost in trouble, so far from home.

I reached for you. My arms were like stone.

Woke, and you were missing.

Missing (x II)

Search for something, to explain.

In the whispering rain, and the trembling leaves.

Tell me baby, where did you go?

You were here just a moment ago.

There’s nights I still hear your footsteps fall.

And I can hear your voice, moving down the hall.

Drifting through the bedroom.

I lie awake but I don’t move.

Bruce Springsteen, Missing.

In the opening scene, set at a group grief counselling session, we are introduced to Bobby, played by John Savage (The Deer Hunter; Do The Right Thing), who has lost his older brother.

Robert De Niro (L) and Savage (R) in Michael Cimino’s The Deer Hunter.

It’s an excellent showcase for Savage, who never found the level of fame that his Deer Hunter castmates (Robert De Niro, Christopher Walken, and Meryl Streep) did. But with only this brief appearance in the opening scene, Savage makes an impression that lingers long after the picture is over.

As Bobby tells us, his deceased brother was the family favourite, “Son number 1.” Bobby was always “Son number 2,” but since his brother’s death, Bobby is “Son number 3,” a nickname for “Bobby, depressed.”

Bobby talks about the piece of himself that died along with his brother. “I miss me,” Bobby says. And that’s the hard truth people don’t talk about – how we become collateral damage when we lose a loved one, and how we have to find a way to mourn that lost version of ourselves.

That loss of self, and of all the collateral damage that follows in death’s wake, is beautifully articulated in brief testimonials from the other members of the therapy group (in what feels more like documentary than drama, but is no less affecting for it), is the true subject of Sean Penn’s haunting, thoughtful screenplay.

Though she doesn’t speak once in the scene, we experience this moment through the eyes of Mary, played by Anjelica Houston (her father, John Huston’s, Prizzi’s Honor; and The Dead), identified by on-screen text as “the mother.” Mary doesn’t need dialogue for us to know that Bobby’s words speak also for her. A solitary tear from a masterful performer like Huston says it all.

Nicholson stars as Freddy Gale, “the father,” a slightly shady downtown LA jeweler drowning himself in booze and strippers in the aftermath of his young daughter, Emily’s, death in a drunk driving incident.

Freddy spends most of his nights in a sleazy stripclub with his drunken, middle-aged loser buddies, in what feels like the 90s equivalent to Cosmo’s joint in John Cassavetes’ The Killing of a Chinese Bookie (1976).

Freddy has no time for group therapy. “I’m a busy man,” he tells us. “Always busy.” And besides that, Freddy has his own plan for combatting grief.

Freddy has marked his calendar. Today is the day the man who killed his daughter is being released from prison, and Freddy is going to kill him.

Played by The Indian Runner’s David Morse (12 Monkeys), John Booth is racked with crippling, gut-twisting guilt ever since accidentally killing Freddy’s and Mary’s little girl. His body may be getting out of prison, but his soul is another matter.

John doesn’t need Freddy to punish him, he’s happily taking care of that himself, as we see in an early flashback where John bashes his head against the bars of his cell, leaving him with a visible scar that can in no way compare to the invisible ones he shares with Freddy and Mary.

That’s the trouble with grief. You can’t see it. If we break our arm, we set the bone and wrap it in a cast. Everyone around us can see that we are injured, and healing. They know to take care around our broken parts. But with grief, there is no bone to set. Nothing to wrap a cast around. No sign of breakage. To everyone around us, we’re in perfect working condition. But we know better. Bobby already warned us.

Freddy, Mary, and John are all broken, but when Freddy shares his plan with Mary, his now ex-wife, remarried to Robbie Robertson (excellent in a rare dramatic performance), who is raising Freddy’s two young sons as if they were his own, she is less than grateful.

What does Freddy hope that murdering John Booth will accomplish? “Pride and relief,” he promises Mary.

Mary chides Freddy. She knows that killing Booth has nothing to do with honoring their dead daughter. It won’t bring her back. Freddy has never even had the courage to visit Emily’s grave.

“You ever have a sound build up in your head over a couple of days?”

Freddy returns to the strip joint, tries talking to his friends about his deteriorating mental state, but they laugh it off. Dismissed by Mary, and now by his pals, Freddy has nowhere to turn but to his ill-conceived plot for vengeance.

John Booth is surprisingly more receptive to Freddy’s plan. When he is confronted by Freddy sticking a gun in his face (fumbling and forgetting to load the weapon – Freddy is no practiced assassin), John seems to accept Freddy’s right to take revenge. We sense that he even welcomes it.

But he asks Freddy to take a couple of days to, “think about maybe not taking my life.” If, once those 72 hours are up, Freddy still wants to kill John, then he will be met with no resistance. “I’m not going anywhere,” John tells Freddy. “I’ll give you three days.” Freddy tells John. Maybe next time, Freddy will even remember to load his gun.

Tagline from poster (detail).

Of course, John is going somewhere. From the moment he is released from prison, he is on a collision course with Freddy. “Some lives cross,” the film’s poster tells us. “Others collide.”

Waking with a hangover and a gun.
Freddy remembers to load the clip.
New death day.

The journey John and Freddy are now on can lead only to one of two places – either Freddy will follow through with his pledge to kill John, continuing the cycle of tragedy and grief that began with his daughter’s death, or somehow, through all of their shared suffering and pain, their inevitable collision will bring about catharsis and change. For both of them.

John has friends and parents who love him, and would mourn him. He doesn’t want to die, but he isn’t sure he deserves to live. He returns home having served his sentence with no greater plan than just to “get on with things.” And over the next 72 hours, he will do just that, knowing that they could be his last three days on the planet.

The events of those next three days will force Freddy, John, and Mary, to confront their guilt, grief, and anger head on. Will they be further casualties of the accident that killed poor little Emily, or will they survive, and by some miracle of the Gods of Forgiveness and Redemption, find peace?

John isn’t asking for anyone’s forgiveness, and he certainly isn’t expecting to find love, but when his best friend, Peter (David Baerwald), introduces him to the beautiful painter, Jo-Jo, at a welcome home party thrown in his honor, suddenly, John finds himself standing across from someone with enough empathy and compassion to see past the death and guilt that have come to define his life, preventing him from really living it.

Freedom is overrated.

John Booth, The Crossing Guard.

A conversation about compassion, and who does, and does not, deserve it, has the flow and feeling of documentary that the opening grief counselling session does. It’s a wonderfully staged, edited, and performed scene which gives John and Jo-Jo time and space to safely size each other up, and grow curious.

Penn (L) and Wright (R) in State of Grace (1990).
Wright (L) and Penn (R) in She’s So Lovely (1997).

Wright (L) and Morse (R) in TCG.

Played by an excellent Robin Wright (The Princess Bride; Forrest Gump), reuniting with her past (State of Grace) and future (She’s So Lovely) co-star, and (now-ex) husband, Penn, Jo-Jo falls for John’s vulnerability, sees his pain, and offers him a port in the storm, a respite from his self-loathing.

Knowing that his days are literally numbered, John continues to sample the new life that awaits him, should Freddy choose to show him mercy, working on a fishing boat with Peter, who warns him that Jo-Jo is special, and to take care with her. “There are women and then there are ladies,” Peter tells John. “Jo-Jo is a lady.”

And as John builds bridges in his relationships, new and old, Freddy burns his own down.

Tickling the ivories.
“You’re always with such pretty girls, Mr. Gale.”
The dinner party.
The old “tongue-in-an-aperitif” trick.
Verna is unimpressed.
Down the hatch!
An interested party.
“You must be a funny guy.”
“I’m a riot.”
“…Now, fuck off!”
Freddy attacks.
They crash into another table.
Freddy’s dates love it, and cheer him on.
But Verna is embarrassed.
Dinner is ruined.
Freddy goes full-WWE Smackdown.
I pity the poor bastard (R) having to hold Freddy back.
At the police station…
Freddy gets fingered.
The experience makes an impression on Freddy.
Mugging for the shot.
The flash of judgment.
Ready for his close-up.
“Where’s the fucking car?”

Intercut with the welcome home party sequence, is one in which Freddy escorts a trio of exotic dancers from the club, including his long-suffering, on-again, off-again girlfriend, Verna (Mallrats’ Priscilla Barnes), to a classy restaurant, only to ruin dinner with a violent outburst that sees him arrested, finger printed, and having his mug shot taken, before the girls can bail him out the next morning.

Searching…
For God.
Finding only…
Ourselves.
A moment of confession.

“The father of the girl I killed threatened to kill me last night. You’re the only one I’ve told.”

John.

“Why me?“

Jo-Jo

“I thought it would be romantic.”

John

Finding no refuge at work, Freddy’s rage and hostility are seeping out of him.

“A perfect fucking seven.”

He takes a little of that toxic bile of fury out on a dissatisfied customer, a ranting-racist played by Penn’s mother, Eileen Ryan.

Meanwhile, though Freddy has been unable to face his daughter’s grave, John visits with flowers.

There he finds Mary lost in thought, as her other children run around playing, without a care in the world. The sight of Emily’s grieving mother only further reminds John of all the pain he has caused and reinforces the idea that maybe his death really would be a fitting justice.

One of my favourite scenes in the picture is one in which a lonely, drunken Freddy visits a run down bar (brothel?) called Dreamland, where the patrons can dance with any of its “100 beautiful girls,” so long as they pay by the song.

A homeless man (played by Sean’s dad, Leo Penn) outside the bar warns Freddy not to enter Dreamland, “Unless you want to fall in love.”

My wife was a beautiful woman…

Freddy

…I met her in the sun… sun… sunny, sun…

Freddy

I could never fall in love at night.

Freddy
Follow the purple light to love (on sale).

And so, immune to any nocturnal amorous temptations, Freddy stumbles into Dreamland, where he does not find love, though he does find a selection of emotionally vacant, but physically available, young “dance partners.”

Lit like subjects for a Caravaggio painting, as a Spanish cover of Aerosmith’s Love Hurts plays on the jukebox, the women’s faces all tell the same, sad, lonely story.

Even in the arms of the woman he dances with, Freddy is totally, completely alone. There is nothing holding him to the earth. No love to tether him. Only hate.

Meanwhile John continues to explore his blossoming romance with Jo-Jo, but his guilt, she tells him, is “a little too much competition.” If they are going to have any chance at a future together, John is going to have to let go of his suffering, and forgive himself.

“Keep dancing”

Only then will John be free to accept love, from Jo-Jo, from his parents, or anyone else. “Let me know when you want life,” Jo-Jo says. But John doesn’t know how to let go of his self-loathing. He’s designated Freddy as his own personal St. Peter, and only Freddy has the power to absolve him. “What is guilt?” John asks Jo-Jo. She doesn’t have an answer. Instead, she asks him, “Do you want to dance?”

But Freddy, things will only get much darker before dawn.

In addition to an ex-wife, and a girlfriend, Freddy also has a mistress (Kari Wuher), Mia, a younger version of Verna, whom he tortures by openly flirting with Mia in front of her, even parading around on stage, to the wild amusement of his drinking buddies, as Verna looks on, trying, and failing, to hide her heartache, and Freddy takes no notice.

His dalliance with Mia proves more annoyance than distraction, as she (hilariously) serenades Freddy with a God-awful love song she has written just for him (“Freddy & Me-ee-ah,” she sings), and Freddy passes out, making him late for his date with John.

In a scene which should have netted them both Oscars, Freddy reaches out for one last desperate Hail Mary pass, calling his ex-wife after waking from a disturbing recurring nightmare.

Mary agrees to meet with Freddy, thinking that his vulnerability is proof that Freddy has turned a new leaf, but their reconciliation is short lived. Freddy’s rage returns, and so does Mary’s contempt.

Like something out of his nightmare, Freddy is haunted by the watchful gaze of a crossing guard as he drifts further away from mercy towards vengeance.

Today is judgement day.

John awaits Freddy’s arrival. There is no doubt that Emily’s father will come. Neither one of these men can escape the other’s trajectory. They are fated to make impact. But will they destroy each other? Or bring about each other’s salvation?

Freddy is delayed by a pair of LAPD officers, who pull him over for driving erratically. When he fails his roadside sobriety test, they attempt to make an arrest, but Freddy runs, and the police give chase.

“Time’s up.”

Freddy reaches John’s trailer but finds John no longer content to play the martyr. John gets the drop on Freddy, pulling a rifle. But John doesn’t want to kill Freddy. And so, now it is John’s turn to run, and Freddy’s turn to chase.

But John isn’t running away from anything. He stops more than once to allow Freddy time to catch up. Rather, John is running to something.

At the gates to the cemetery where Emily is buried, Freddy catches up to John. And as the younger man scales the fence, Freddy takes aim and fires. He clips, but does not deter, John, who rises and continues on, ultimately, to Emily’s grave.

What transpires between them as they kneel before Emily’s pink stone, is one of the most empathetic moments of any film from the 90s, or any other decade. If revenge is swallowing poison hoping that the other person will die, then forgiveness is feeding the other guy medicine and discovering that you get well, too.

Through the road was paved with hate, it has led Freddy here, back to Emily, whose loss rendered him this dedicated husk of a man. But now his anger melts away. All that is left is his grief. Finally Freddy is ready to mourn his daughter. The road ahead is long. It stretches as far as the eye can see. But hate is no longer behind the wheel. There is room for love. For Freddy, and for John. Through Freddy’s forgiveness and mercy, John is now ready to forgive himself, too.

Dawn breaks. Mary, her husband and kids, Peter, John’s parents, and of course, Jo-Jo, will all soon be waking. Maybe now, in the light of a new day, Freddy and John will be ready to face them. They want life again.

The Crossing Guard is the type of character-driven, adult-themed drama that New Hollywood turned out like hotcakes in the years between Bonnie and Clyde (1967), and Heaven’s Gate (1980).

Legendary cinematographer, Vilmos Zsigmond (R), with Nicholson (L) on location for The Crossing Guard.
Publicity photo.
Zsigmond, Man With A Movie Camera.

Penn’s choice of Vilmos Zsigmond as DOP ensured that TCG, at the very least, looked like one of those 70s masterpieces.

Zsigmond (R), (literally) working under genius director, Robert Altman (L).
Zsigmond (L) with Cimino (C) and De Niro (R) on location for The Deer Hunter.

Zsigmond was responsible for lensing some of that decade’s most beautiful and iconic pictures, from Robert Altman’s McCabe & Mrs. Miller (1971), and The Long Goodbye (1973), to John Boorman’s Deliverance (1972), Brian De Palma’s Obsession (1976), Steven Spielberg’s Close Encounters of the Third Kind (1977), and Michael Cimino’s The Deer Hunter (1978).

Troubled, but brilliant composer, Jack Nitzsche.
Theme by Jack Nitzsche.

And Penn’s selection of Jack Nitzsche to compose the score, made sure that TCG sounded like a long, lost 70s picture, too.

Excerpt from Jack Nitzsche’s score.
Photo by the author.

I first saw The Crossing Guard at TIFF, when it was still referred to as “The Festival of Festivals.” It was my first exposure to the film festival, or any film festival, for that matter, an exclusive gala screening at Toronto’s magnificent Roy Thompson Hall.

Writer-director Sean Penn on the red carpet at an event for The Crossing Guard.

Sean Penn attended the gala to introduce his film and stepped on stage, smoking a cigarette (despite RTH being a strictly no-smoking venue), to declare that, although he wasn’t there in person, what the audience was about to see on screen represented Jack’s “blood, sweat, and tears.” Penn’s own blood, sweat, and tears were all over the screen, too. The film is all heart (and heartbreak).

Penn and Nicholson would reunite on the former’s next directorial effort, the very good The Pledge, another harrowing, emotional drama with exceptional performances (despite an unfortunately cast Benicio Del Toro as a mentally-diminished Indigenous man). But it is The Crossing Guard that I believe represents their greatest work together, and possibly their greatest work, full stop.

Penn (R), with Wright (C), and Gary Oldman in Phil Joanu’s State of Grace (1990).
Theatrical poster.
Penn, unrecognizable as Kleinfeld, Pacino’s double-crossing lawyer in Brian De Palma’s Carlito’s Way (1993).

Penn famously took a three-year break from acting between 1990’s Irish-mob drama, State of Grace, and 1993’s melancholy gangster picture, Carlito’s Way, during which time he wrote and directed The Indian Runner.

Following The Pledge, Penn would have a hit with 2007’s Into The Wild, and a miss with 2016’s The Last Face. I’ve yet to see 2021’s Flag Day, but I have high hopes.

On screen, Penn followed The Crossing Guard with Oscar-nominations for Best Actor in Dead Man Walking (one of his best), the same year that TCG was released, and in 2002 for I Am Sam (not one of his best).

He won the gold statue twice, for Clint Eastwood’s Mystic River (2003), and Gus Van Sant’s Harvey Milk bio-pic Milk (2009).

Penn’s star has fallen somewhat in recent years, with pictures like The Gunman (2015), and Asphalt City (2023), failing to connect with either audiences or critics, but with the upcoming release of Paul Thomas Anderson’s One Battle After Another (2025), he may soon be on the precipice of a major acting comeback. Only time will tell if he has enough blood, sweat, and tears left to deliver another Crossing Guard.

And with Nicholson happily and officially retired since co-starring with Morgan Freeman in Rob Reiner’s The Bucket List (2007), I’m confident we will never see a greater performance from Jack than the one he gifted us with his portrayal of Freddy Gale in Penn’s excellent and criminally overlooked 90s masterpiece.

Japanese poster.

Like those great actors of the 70s, a period to which this film spiritually belongs, The Crossing Guard has only matured and ripened with age. It’s a film I intend to grow old with. As a 15 year-old falling in love with the movies for the first time, I didn’t just see this film, I collided with it.