Carlito’s Way (Universal, Epic Productions, Bregman-Baer Productions, 1993)

by Mark Gabrish Conlan • Copyright © 2021 by Mark Gabrish Conlan • All rights reserved

Last night at 9 p.m. I ran a movie from the backlog that turned out to be unexpectedly good: Carlito’s Way, a 1993 film directed by Brian De Palma and starring Al Pacino. Of course this movie was the Hollywood Xerox Machine in full operation – four years before, in 1989, De Palma and Pacino had made the successful remake of the 1932 gangster classic Scarface, changing the original story (an Italian gangster muscling his way into the illegal booze business during Prohibition) into one of a Cuban immigrant muscling his way into the illegal cocaine business. So obviously Universal thought the combination of De Palma, Pacino and a story about a Latino gangster would be another success – only this time I think they did it better. We first meet Our (Anti-)Hero, Carlito Brigante (his Anglo friends call him “Charles”), having just been shot, apparently fatally, on the streets of New York City, and then we get a flashback narrated by Carlito himself detailing how he got there. The film was written by David Koepp from two novels, Carlito’s Way and After Hours, by Edwin Torres, and it takes place in 1975 because that’s when Torres published the Carlito’s Way book. (De Palma deserves credit for filling his soundtrack with all the terrible disco songs that were popular in 1975, many of which I rememberd … and wish could have stayed forgotten.)

The extended flashback that makes up the core of the movie (like the 2000 film American Beauty, this is less a whodunit than a whosgonnadoit) starts out in a courtroom in which Carlito is about to be sprung from a 30-year sentence for murder and drug dealing because his attorney, Kleinfeld (Sean Penn, in a virtually unrecognizable makeup that both my husband Charles and I thought made him look like Art Garfunkel), discovered that the wiretaps that generated the tapes that were the principal evidence against him were made illegally. Much to the disgust of the judge in the case as well as Norwalk (James Rebhorn), the district attorney who prosecuted him (and makes it clear that he expects to prosecute him again, sort of like Javert in Les Misérables), they’re forced to set Carlito free and in a flamboyant speech he insists on making to the judge (who just wants to get him out of there so he can move on to the next case on his docket), he swears he’s had enough of a life of crime and intends to lead a law-abiding life from now on. He continues his Big Speech on the steps of the courthouse and ends it the way Martin Luther King, Jr. ended his speech at the 1963 March on Washington: “Free at last, free at last, thank God almighty, I’m free at last!” (I joked that what he really meant was, “Coppola and Pollack wouldn’t let me overact, but with De Palma as my director, I’m free at last!”)

Of course Carlito’s resolution to avoid a life of crime doesn’ last more than a few minutes of running time, and the temptations of “the street” (projected in this movie as a sort of living force of its own) soon swallow him up. He’s persuaded by his young cousin to accompany him in a cocaine delivery which ends up in a shoot-out in a pool room (as William K. Everson noted in his book The Detective in Film, pool rooms have been hangouts for movie criminals since the Edison company made the first gangster film in 1912) and the cousin dead. Carlito’s dream is to raise $75,000 so he can flee to Bermuda and buy a share in a car rental business there – there’s even a billboard advertising Bermuda as “Paradise” that becomes a running motif the way the Cook’s Tour slogan “The World Is Yours” became a running motif in both versions of Scarface) – and to get the money at least semi-legally he takes a job running a Studio 54-style disco (also called “Paradise” in Spanish, ironically) because the lead partner Saso (Jorge Porcel) is a gambling addict and the other people involved in the club are worried that left to his own devices, he’d gamble away all the proceeds. Along the way he starts dating Gail (Penelope Ann Miller), whom he’d known before he went to prison as an aspiring Broadway star but who’s now reduced to working as a stripper in a sleazy club. Though she’s not required actually to have sex with the customers, she does do a lot of walking around topless, and it’s a tribute to Penelope Ann Miller’s talent as an actress that she’s able to maintain a sense of dignity and pride while showing her quite nicely formed breasts on camera through a lot of the film.

The two start an affair and he plans to take her to Bermuda with him as soon as he’s accumulated the $75,000 – but they don’t because Carlito’s rise is paralleled with the fall of his attorney Kleinfeld. We’re told that Kleinfeld started out as a junior attorney in a law firm whose main business was representing Mafiosi, and as he’s risen through the legal profession he’s taken on a lot of “wiseguy” clients of his own and also developed a heavy-duty coke habit. The final catastrophe that throws Carlito’s careful game off balance and leads to his downfall starts when one of Kleinfeld’s Mob clients, Vinnie Taglialucci (Joseph Siravo), demands that Kleinfeld help him break out of jail at Riker’s Island. The idea is Vinnie has bribed a guard to let him jump off the barge that apparently contains at least part of Riker’s operations, where he’ll swim out to a buoy and Kleinfeld will drive by in a power boat and pick him up. Only Kleinfeld wants Carlito to come along – and Vinnie insists that his son Frankie (Adrian Pasdar) be there too. The three uncertain and very reluctant co-conspirators sail out and duly pick up Vinnie – only instead of getting him onto the boat Kleinfeld clubs Vinnie to death with the grappling pole, then shoots Frankie, meaning that both he and Carlito will immediately go on the Mob’s hit list for having offed two “made men.”

D.A. Norwalk calls Carlito in and plays him a tape in which Kleinfeld acknowledged that his whole purpose behind bringing Carlito along was to set him up and frame him with the Mob, and offers him immunity and relocation if he’ll testify against Kleinfeld. Carlito refuses and plots with Gail to take a train to Miami, from which they can book a plane to Nassau, but of course he’s caught by the Mob and gunned down after an extended and quite effective suspense sequence in which he barely makes it to Grand Central Station after a subway ride in which he barely manages to avert assassiation by a hit squad led by Vinnie’s other son, Tony (Frank Minucci). Carlito also finds that the safe in the disco where he was keeping his cash has been emptied and only a small portion of it remains in a box under the club’s bar; he retrieves what he has left (Charles was critical of this movie, as he often is, because the bulk of money we see doesn’t correspond to how much space $75,000 would really take – but I thought the point was that the money in the box was just a small fraction of Carlito’s savings but was all that was left after Sosa stole it and likely gambled away the rest) and he’s able to give the rest to Gail, encouraging her to take the train to Miami and start a new life, before he expires (or at least is rushed to an emergency room – we’re never definitively told whether Carlito lives or dies, though the implication of the narration is these are his last thoughts before he expires).

I liked Carlito’s Way considerably better than I’d liked the De Palma-Pacino Scarface, and I think it’s because here Pacino was playing a far more complex character: in Scarface he was just a monster but here he’s genuinely conflicted, with his dream of leading a decent, non-criminal life conflicting with the reality he’s stuck with and the lure of “the street.” I liked the way David Koepp practiced the old classic Hollywood art of “planting” – establishing critical details early on in the story that will be recycled and restated to become major plot points later on – and indeed, though the film was made in 1993 and the setting is 1975, there’s a lot of the best elements of 1930’s gangster films in it and one could readily imagine James Cagney or Humphrey Bogart playing a similar story in the classic era. Also, like Martin Scorsese’s GoodFellas (which I held off watching for years expecting it to be a virtual start-to-finish bloodbath), there’s actually surprisingly little outright violence in this film – just enough to keep us aware that, even though they have genuinely sympathetic qualities, these are still people who kill other people for a living and we can’t be allowed to forget that about them. I was curious about Carlito’s Way (an item I pulled from our DVD backlog) especially after the night I watched two of De Palma’s early films, Sisters and Obsession, on TCM and was curious about catching up with one of his lesser known later movies – and I quite liked Carlito’s Way (more than Charles did, I suspect). It’s not a great movie, but it is a surprisingly good one and, though it’s 2 hours and 20 minutes long, the story is legitimately complex and De Palma moves it along and paces it so it doesn’t seem padded, the way quite a few similarly long movies do today.