Jack Nicholson: 25 Essential Movies

Legendary “King of the B’s” Roger Corman met the young Nicholson in an acting class, and ended up giving him his first movie role in the 1958 pulp cheapie The Cry Baby Killer; it was the beginning of a beautiful friendship, as well as a professional relationship that would sustain the actor throughout the Sixties. (“Roger was the only guy who’d hire me for 10 years,” he claimed.) And when you watch Nicholson’s extended cameo in Corman’s horror-comedy about a misfit and his man-eating plant, you can see why the director-producer loved him. Rocking a dweebish middle-part haircut and a more-nasal-than-usual voice, Nicholson’s giggling masochist comes to check out the most sadistic dentist in town. Instead, he gets the movie’s hero, who doesn’t know the first thing about drilling teeth. No matter — Nicholson’s pain addict leaves satisfied. He’s only onscreen for roughly three minutes, but from the way he yells, “Oh my god, don’t stop now!” when the amateur hits a nerve, you could already tell you were in the presence of a performer up for anything.

Nicholson ended up becoming a Jack-of-all-trades in Corman’s rep company, serving as a writer, a co-producer, and an actor in everything from American International Pictures’ horror films to biker flicks. It was his involvement in two Westerns executive-produced by Corman and directed by Monte Hellman, however, that marked the high point of Nicholson’s involvement with the the exploitation-cinema guru. Shot back-to-back in the stark deserts of Utah, Ride the Whirlwind and The Shooting were bleak, existentialist horse operas that drift into head-trip territory — and you know everything about his character in the latter movie from the moment he slowly trots into the frame. The black leather gloves, the well-handled six-shooters, the don’t-give-a-fuck sneer: He’s an archetype, the young punk with an extremely quick draw. It was an early example of how Nicholson could use screen presence to do the heavy lifting. You never really find out how or why his gunslinger ends up in the company of his fellow travelers (including a particularly sweaty Warren Oates), but you can tell he’s trouble.

It was Nicholson who helped bring Peter Fonda and Dennis Hopper’s movie about hippies motorcycling across America to his pals Bert Schneider and Bob Rafelson, who’d end up producing the film. It was Nicholson who saw the early potential of this druggy drive-in flick; he’s quoted in Patrick McGilligan’s biography Jack’s Life as saying it could be “the Stagecoach of bike movies.” It was not Nicholson who the duo wanted for the role of George Hanson, the Southern ACLU lawyer who briefly tags along with the longhairs, but as their original choice Rip Torn had backed out and production was getting underway, they eventually relented under pressure. Yet the moment Hanson appears onscreen, complaining about last night’s bender, it’s like you can hear something click into place. His “straight” character in the football helmet balances out the freaks. His offscreen bonding with Fonda and Hopper translates into a nice rapport when it comes time for a stoned Hanson to wax rhapsodic about Venusians. Then comes Nicholson’s speech about how the establishment “is scared of what you represent to them … and what you represent to them is freedom,” and suddenly, you’re no longer watching that guy from the Corman films with the nasal twang and receding hairline. You’re watching a grade-A, genuine movie star.

Easy Rider had been a game-changer for Nicholson, but it was Bob Rafelson’s movie about a concert pianist from a rich family who prefers a working-class life that would establish him as leading-man material. His Bobby Dupea is the first of many characters he’d play that are caught between two worlds — in this angry young man’s case, a “real” life of honky-tonks and oil-rigging gigs, and the “phony” life of professional musicians, mansions, and mute, unloving fathers. Dupea doesn’t fit into either world, and like a lot of future Nicholson guys, he doesn’t want to be tied down by anybody, either. There are a ton of standout Jack moments here, from an impromptu recital on the back of a truck to a heart-wrenching speech to his dad about being a disappointment. What everyone remembers is the diner scene, even if no one involved can remember exactly who came up with it; Nicholson traces part of it back to his own experience hanging out in a coffee shop one day on the Sunset Strip. A simple request to a waitress regarding a side of toast escalates into a weapons-grade putdown (“You want me to hold the chicken?” “I want you to hold it between your knees!”) and the clearing of a cluttered table. Sarcasm, frustration, a smile that doubled as the baring of teeth, and a sudden eruption of white-hot fury — the Age of Jack had begun in earnest.

Mike Nichols and Jules Feiffer’s indictment of the 20th-century American male remains one of the most merciless, brutally honest movies of the Me Decade — and there may not be a Senenties lead character harder to sympathize with than Nicholson’s misogynistic Jonathan Fuerst (only Taxi Driver‘s Travis Bickle comes close). Charting the friendship of two men from their college days to middle age, this controversial character study underlined Nicholson’s generosity as an actor (he was the second best partner Art Garfunkel ever had) and his fearlessness when it came to depicting men behaving badly, psychological warts and all. “You know you’re a prick, right?” one character rhetorically asks Fuerst, and the actor makes sure we know it, too. The fact that Nicholson was already garnering a reputation as a love-’em-and-leave-’em type adds a whole other layer to his toxic womanizer, and it’s still shocking to see his volcanic rage — deployed to such gleefully rebellious effect in Five Easy Pieces — aimed full-blast on Ann Margret’s hapless trophy girlfriend. It’s an ugly, take-no-prisoners performance, and still one of Nicholson’s best.

“Tell [the] M.A. to go fuck himself”: That’s the first full line given to longtime Navy lifer Billy “Badass” Buddusky, delivered in a semi-awake, fully hungover bark. (M.A. stands for “master-at-arms.”) One sentence and you already get a clear sense of who this guy is and how much shit he’ll take. (Answer: zero.) Nicholson’s signalman is assigned alongside fellow military man Otis Young to escort Randy Quaid’s baby-faced sailor to the brig. The 18-year-old has been court-martialed for trying to steal $40; in the spirit of sympathy, the two gents treat him to a few whirlwind days in New York City before his sentence begins. “It’s a story of military justice … or rather, military injustice,” Nicholson told an interviewer at the time — but Hal Ashby’s surprisingly tender film is also a tale of father figures, flinty male friendships, and the sort of salty-dog culture that guys like Buddusky thrive in. As for Nicholson, he’s locked in to the heart of a guy who knows this kid is getting a bum deal while having the time of his life saying screenwriter Robert Towne’s course, colorful dialogue. Both that famous shit-eating grin and the actor’s facility for exploding get a great workout here, especially when Nicholson is told by a bartender to cool it or he’ll call the shore patrol. The classic, screamed response: “I am the fucking shore patrol, motherfucker!”

“I’m a romantic,” Nicholson is quoted as saying in The Big Goodbye, Sam Wasson’s book on the making of Chinatown. “I allow myself to think that things could be better, could be more than they are.” Read that and you can see why playing Jake Gittes appealed to him — never mind that it was a great part, in a great script by Robert Towne, with a great Hollywood producer, and a great European director attached to it. A former cop haunted by a tragedy in the neighborhood that gives this classic its title, Gittes is now a private dick sticking his (soon-to-be-sliced-open) nose into other people’s affairs. He’s learned his lesson; things will be better. Then Gittes takes a case involving a rich dame’s husband, and keeps digging deeper and deeper, and it all goes to hell in a spectacular way. Nicholson somehow manages to channel both a 1937 detective and someone suffering from a specific spirit-of-’74 sense of disillusionment — a tarnished white knight in a Nixon-era throwback noir. He’s bold, brash, dapper-looking in his period duds, sarcastic, sexy, and firing on all movie-star pistons. This is a hero who has all the answers and will save the day, Nicholson seems to be telling us. And then those gunshots ring out at the end, and the look on his face when someone tells him to “Forget it, Jake, it’s Chinatown” just devastates you.

Brando said no. So did James Caan, Gene Hackman, and Burt Reynolds. Kirk Douglas, who’d played Randle “R.P.” McMurphy on Broadway in the early Sixties and had tried to turn Ken Kesey’s novel into a movie for years, wanted a crack at it — but the producer who held the rights, i.e., his son Michael, thought Dad had aged out of the part. Eventually, someone suggested Nicholson, who’d taken a liking to this story involving a free spirit fighting against the establishment. And, well, you know the rest. McMurphy was prime Nicholson, a rebel with a cause that once again allowed the actor to tap into something charismatic and countercultural, only on a much larger scale. It’s now impossible to think of anyone else who could have captured that particular anarchic quality of Kesey’s antihero, trying to liberate his fellow mental-institute patients while standing up to the human iceberg that is Louise Fletcher’s Nurse Ratched. (Finally, a formidable nemesis for his fits of rage!) There are a number of big standout scenes for Nicholson in Milos Forman’s classic, from McMurphy giving a play-by-play of an imaginary World Series game to the violent attack that finally gets him lobotomized. But Nicholson does wonders with the small throwaway moments as well — watch the way he gently replicates William Redfield’s hand gestures during a rant while giggling to himself, or the dual reaction shots he gives Will Sampson when the silent man speaks. It won him his first of three Oscars. It still feels like the perfect example of what made Nicholson’s work during this decade so exhilarating.

Nicholson had been dying to make a movie with Michelangelo Antonioni ever since Blow-Up had firmly established the Italian filmmaker as the arthouse auteur du jour: “I wanted to be a film director, and I thought I could learn from a master,” the actor confessed. The end result of their collaboration remains a curious entry in Nicholson’s Seventies run of characters escaping from social constraints, previous lives, and their own cracked sense of self. While on assignment in Africa, a TV journalist strikes up a conversation with a fellow traveler. The man later turns up murdered, at which point the reporter takes on the dead man’s identity. International arms deals, avoiding law-enforcement officers, and an affair with a college student (Last Tango in Paris‘ Maria Schneider) ensue. Antonioni had always adopted a less-is-more attitude when it came to actors, and Nicholson later admitted that he found the lack of communication and cryptic attitude toward basic story elements a little frustrating. But Nicholson’s minimalist turn here is perfectly attuned to what’s happening onscreen. Looking back at The Passenger in 2005, New York Times critic Manohla Dargis described the performance as “a stunning admixture of emotional lethargy and sexual heat” — which nails his smoldering-alienation-chic vibe here to a tee.

Nicholson’s only pairing with fellow screen legend (and Mulholland Drive neighbor) Marlon Brando is an odd Western even by Seventies standards — name another movie in which a curiously Irish-accented Brando murders someone while wearing a bonnet and dress. Jack is the head of a gang of cattle rustlers who, under the cover of being a farmer, seeks revenge against a rich landowner; the Godfather star is a “regulator” hired to exterminate these thieves with extreme prejudice. Acting alongside his idol was a dream come true for Nicholson — “I studied him then,” he said, referring to watching Brando in the 1950s, “and I find myself now, even when I’m working with him, wanting to emulate him” — yet rather than try to match Marlon for sheer out-there-ness, the younger actor goes the opposite route and tamps things down. It’s one of the few Nicholson movies in which he’s the grounding force, which pays off in Breaks’ best scene: Brando trying to goad his enemy into a gunfight while Nicholson silently bides his time. And while the stars’ final showdown is a little anticlimactic, Jack still turns a hissed threat (“Ya wanna know what woke ya up?”) into the most menacing kiss-off imaginable.

“Here’s Johnny!” The knock on Nicholson’s performance in Stanley Kubrick’s modern horror classic has always been that there’s little sense of his character — former alcoholic, frustrated writer, and homicidal father Jack Torrance — going mad: He seems to shift gears from “normal” directly into Full Metal Jack-ed. “When the material is as unusual as The Shining, dealing with ghosts and spirits, the acting has to be larger than life,” he said in an interview shortly after the film’s release, and whether the scene called for him to swing an axe or chat up a spectral bartender, it’s a notion he took to heart. But it’s less of a 0-to-160-mph ramp-up than you might think, and there are a lot more subtle shadings leading up to that manic last half hour. On repeat viewings, you can appreciate how the actor plants seeds in earlier sequences that will slowly bloom into insanity. Indeed, some of the most chilling moments in this haunted-hotel nightmare literally involve little more than Nicholson staring silently ahead, his head tilted down in signature Kubrick-protagonist fashion. Author Stephen King infamously hated this adaptation of his novel, yet Nicholson gets at something that is key in both the literary and screen versions: Inside every family man is a raging monster. And for some men, that monster is the real caretaker. It’s always been the caretaker.

Nicholson had wanted to do a remake of James M. Cain’s pulp novel since the early Seventies, right as he was becoming a bankable name. (The director he wanted to helm it? Hal Ashby. The original actress he wanted to cast as the female lead? His then-girlfriend, the Mamas and the Papas’ singer Michelle Phillips.) By the time he and director Bob Rafelson got around to adapting this sordid tale of infidelity and murder almost a decade later, Nicholson was in his early forties, adding an even rougher, wearier edge to doomed drifter Frank Chambers. (Preparation involved reading The Executioner’s Song, as the star saw an odd kinship between his character and convicted killer Gary Gilmore.) He was also interested in playing up the sexuality of Cain’s book, which resulted in a then-infamous sequence involving Nicholson and co-star Jessica Lange going at each other on a restaurant’s kitchen table like animals in heat. When Chambers and Lange’s restless waitress Cora decide to murder her husband, both actors lean heavily into the fatalism — you can feel Nicholson, sleazier and grubbier than usual, enjoying the chance to indulge in the noir-ish storytelling of another era. In his hands, it would just be more down and dirty than usual.

Legend has it that Nicholson met his one true soulmate at a dual film party just outside of Vancouver, while he was shooting Carnal Knowledge. The cast of a different production — a Western directed by Robert Altman — was also blowing off steam when Nicholson spotted someone across the room. “That’s what a movie star is supposed to look like,” Jack allegedly declared upon meeting Warren Beatty, and boom — it was love at first sight. The two buddies spent most of the next decade hanging out and competing for the title of biggest Hollywood lothario; their one project together, The Fortune (1975), didn’t necessarily suggest that they were a natural screen duo as well. Still, when Beatty came calling about a supporting part in his epic movie about journalist John Reed, Nicholson reluctantly accepted the challenge. He was nervous about playing American theater legend (and one-third of a love triangle involving Reed and Louise Bryant) Eugene O’Neill, as it was the first biographical role he’d ever done. Yet Nicholson handles his scenes with Beatty and Keaton beautifully — if anything, you wish he was in the movie more. He also lends a bitter undertone to the sequence in which the woman he loved returns to see him years later. After goading Bryant into insulting him and losing her cool, the playwright replies, “I seem to have touched a wound.” The fact that Nicholson practically whispers the line only makes it that much more lethal.

You won’t find Garrett Breedlove, ex-astronaut and current over-the-hill Casanova, in the late, great Larry McMurty’s book that this Oscar-winning movie is based on — writer-director James L. Brooks came up with the character himself. And you could technically argue that Nicholson’s next-door neighbor is peripheral to the story of a tempestuous relationship between a mother (Shirley MacLaine) and her terminally ill adult daughter (Debra Winger). But there’s a 10,000-watt current every time he and MacLaine are in a scene together, as these two go from you-disgust-me animosity to I-love-you passion and affection. This is arguably Nicholson’s greatest romantic role, largely because he’s equally matched by his co-star in terms of wariness, wit, and no-bullshit bluntness. There’s such a perfect push-pull dynamic between the two, whether he’s being extra boorish to offset her priggishness (he makes “You wanna have lunch?” sound like the dirtiest question imaginable), or they’re matching each other move for move (when he grabs her ass during a goodbye kiss, she immediately grabs his right back). And the part not only took full advantage of the leering sex appeal that had long been a Jack specialty, but also brought out Nicholson’s inner physical comedian — the graceless way he slides across his Corvette’s dinged-up hood after a disastrous first date is priceless. The film won MacLaine her first Oscar and Nicholson his third. They both deserved it.

It’s love at first sight for Charlie Partanna when he sees the gorgeous blonde from across the room at a wedding. Soon, wedding bells are ringing for this longtime Mob enforcer for Brooklyn’s Prizzi family and his new lady friend, Irene. There’s just one catch: She’s also in the killing-for-hire business. Still, this couple can overcome professional overlap in the name of personal bliss, right? “I did not know it was a comedy the first few times through, including having read [Richard Condon’s] novel,” the star admitted, and had worries that doing a gangster with a dem-dese-dose-level outer-borough accent would turn into a caricature. (Nicholson had turned down the role of Michael Corleone in The Godfather because, he said, it should go to an Italian actor.) But he was in love with the idea of working with his personal hero/Chinatown co-star John Huston, who was directing, so Jack jumped in — and gave a truly incredible performance as a lovelorn lunkhead. His chemistry with both Kathleen Turner and real-life girlfriend Angelica Huston, playing Charlie’s vengeful ex, gives this black comedy a buoyancy, as well as a sexed-up heft. And while Partanna may be the single dumbest character Nicholson ever played, it never devolves into wink-wink idiocy. Stupidity suited him, or as he put it, “I let the character’s limitations keep me happy.”

Nicholson came into this project at the last minute, replacing another actor at the request of director Mike Nichols. “I was working three days after I read the script,” he said. “It was interesting for me at this stage to just go off on something. The framework is usually months of preparation. You don’t get many unusual experiences at this level.” Given that Nora Ephron’s scorched-earth novel was about the dissolution of her marriage to Carl Bernstein, folks wondered if Nicholson would be playing a caricature of a cheating husband. Instead, he went the opposite route, tamping down the ain’t-I-a-stinker charm and playing the political columnist Mark Forman as a serial philanderer that’s recognizably human. Watching Nicholson and Meryl Streep flirt and bicker — this was the first time they shared the screen together — you can feel the joy of two actors finding a push-pull rhythm with each other. And when the star sings a snatch from Carousel‘s “Soliloquy” while shoveling pizza into his mouth, it’s a great example of channeling the “Jack” persona into a character moment rather than merely chewing the scenery.

Nicholson’s part in James L. Brooks’ comedy is little more than a cameo — it was a favor for a friend, and he insisted that he not be credited until the film’s end. But it’s a lovely little grace note in this comedy about a TV producer (Holly Hunter), her besotted best friend (Albert Brooks), and the handsome broadcast reporter (William Hurt) who isn’t afraid to be manipulative or melodramatic to get his field pieces on the air. It’s as much a satire as a rom-com, poking steadily at the notion that the nightly news was beginning to slide into infotainment territory. Nicholson’s Cronkite-esque anchor represents the old school, an éminence grise with the gravitas to give viewers the world in a half hour (though don’t joke about him taking a salary cut to stop staff layoffs). And it’s worth it just to see the look on his face when, after a report featuring an insert of Hurt crying while talking to an assault victim, the camera cuts back to him in the studio and he seems momentarily thrown for a loop.

There are self-effacing screen entrances, and then there’s the introduction that Nicholson’s character gets in this adaptation of William Kennedy’s Pulitzer Prize-winning novel: a pile of trash that soon stirs and reveals itself to be a human being, sleeping on a cold, Depression-era Albany sidewalk. Nicholson’s Francis Phelan is a drifter and a drunk, and an example of an old-fashioned bum. He’s returned to his hometown for the first time in decades, to face down his demons. And though Nicholson’s chummy chemistry with co-star Tom Waits makes you wish these guys had done a production of Waiting for Godot back in the day, his performance essentially drags viewers along for one long, dark night of the soul. “It’s an expiation of sin,” Nicholson said when asked about the role, and you can feel the actor tearing out his guts in a graveyard monologue that spells out the tragedy behind Phelan’s exodus. Both Nicholson and Meryl Streep, playing a fellow barfly, earned Oscar nominations; he’d win Best Actor awards from both New York and Los Angeles critics’ organizations.

Nicholson had portrayed a number of metaphorical princes of darkness by this point in his career — so why not just play Ol’ Scratch himself? Bill Murray had potentially been slated to take on Daryl Van Horne, the mystery man from hell (no, really), in George Miller’s big-screen adaptation of John Updike’s novel. Nicholson eventually stepped in as the silver-tongued devil who’s summoned by, and then seduces, the holy trinity of Cher, Susan Sarandon, and Michelle Pfeiffer. And to say that the actor takes to the part with gusto would be understating it. (The temptation is to think that this isn’t the first time Nicholson has uttered some of these beguiling come-ons so much as the only time he’s done it with cameras running.) It’s a performance that plays off his own hedonistic persona wonderfully — “I see men running around, trying to put their dicks into everything, trying to make something happen!” — and gave him license to sport a ponytail that not even Satan himself could pull off. The shoot was a tempestuous one by all accounts, yet the end result suggests that Jack was clearly having a blast. Here was a role whose appetites came close to matching his own.

It was a high-concept casting coup: The impish id of New Hollywood as the most iconic joker of them all. “I don’t think there was ever a part more tailor-made for him,” production designer Anton Furst was quoted as saying to a Cinefanstastique journalist in regards to Nicholson; no less than Batman’s original co-creator Bob Kane, hired on as a consultant to Tim Burton’s game-changing blockbuster, imagined Jack as the perfect actor to play the Caped Crusader’s nemesis. The role gave the star license to go as over-the-top as he wanted, and with that grotesque ear-to-ear grin, maniacal giggle, and line readings that go to 11, his Joker is the jolt of adrenaline this dark, gloomy superhero movie needed. Subtlety was never in the cards here — Nicholson’s broad, batshit-crazy performance emphasizes how much fun this supervillain is having in unleashing mayhem on Gotham City. His singular take on the Clown Prince of Crime would end up being the missing link between Cesar Romero’s pop-art goof and Heath Ledger’s psychopath in pancake makeup. And while so much of this revisionist take on the Batman mythos has aged badly, the sight of a purple-suited Nicholson dancing through an art gallery to a Prince song somehow still feels timeless.

Nicholson is only in four scenes in Rob Reiner’s adaptation of Aaron Sorkin’s play, but chances are good you remember that last one very, very well. By the time his Col. Nathan R. Jessup strides into the courtroom where two of his men are on trial for murdering a fellow soldier, he’s established that this alpha marine rules over his Guantanamo Bay base with an iron fist (and can tear into Sorkin’s dialogue like it was a rare T-bone steak). You don’t mess with this man, in other words — unless you’re Tom Cruise’s hotshot Navy lawyer. Nicholson’s gradual unraveling on the stand is a thing to behold, as he goes from slow-burn anger to nuclear explosion; any actor could have turned “You can’t handle the truth!” into a few good moments of screen time, but only someone like Jack could make the line both unforgettable and endlessly quotable. He supposedly did more than 40 takes of his meltdown speech, and went full bore every single time even if when the camera wasn’t on him.

Whether you think James Riddle Hoffa — Teamsters president, thorn in RFK’s side, a more than casual associate of the Mob — is deserving of a there-goeth-the-great-man biopic is debatable. What is inarguable is that, once Nicholson signed on to play the labor icon for director Danny DeVito, the actor dove headfirst into the role. He read everything about Hoffa he could get his hands on, studied interviews like a coach watches past game footage, spoke to a number of folks who knew the man (including, apparently, the attorney who prosecuted Hoffa for jury tampering). He affected Hoffa’s Midwestern tough-guy accent, and slapped on prosthetics to help replicate Hoffa’s roughed-up mug. And while you wouldn’t say Nicholson disappears into the role, that ends up being a feature instead of a bug — the main reason to see this movie is the sheer pleasure or watching Jack do Jimmy. He plays the union leader like a pugilist perpetually entering a ring and ready to go 10 rounds with whomever stands in his way. It’s Nicholson who makes you feel like you’re watching an old Warners’ social drama; biographer Patrick McGilligan nails it when he says that, after years of channeling Brando and Bogart in roles, Jack finally got around to giving his great James Cagney performance.

He’s anti-semitic, homophobic, misogynistic, misanthropic, and neurotic to a fault — the first thing we see Melvin Udall do is throw a tiny dog down an apartment chute. He’s not someone you expect to see as a romantic interest in a rom-com, to say the least. And he’s definitely not the kind of role you read on the page and think, “This has Best Actor Oscar written all over it!” But you can see why James L. Brooks wanted Nicholson to take this part in his uptown dramedy about an obsessive-compulsive novelist, a gay painter (Greg Kinnear), and a waitress (Helen Hunt) dealing with a sick son. It would take someone with Nicholson’s ability to keep the audience on his side while he eventually learns to play nice with others. Plus, he can sell a line like “You make me want to be a better man” without drowning the notion in easy sentiment or playing it for sympathy. And to the star’s credit, he doesn’t sand down Melvin’s rough edges, either. “I can’t remember a part that left me more mentally exhausted,” Nicholson would say later, though the effort paid off: It would nab the star his fourth Academy Award.

Director Alexander Payne told Nicholson that Warren Schmidt, the retiree at the center of their 2002 collaboration, was “a small man,” the star said to The New York Times. “That’s what I gave him.” The widower that Nicholson gifts the movie with is indeed someone who seems diminished by circumstance and age. But more importantly, the actor shows us a lost man — someone who drives around in his luxury Winnebago not in search of America but a sense of self. It’s a great lion-in-winter performance from Nicholson, though not in the vainglorious or take-a-victory-lap way usually associated with that phrase. He doesn’t just push his screen persona to the side (Nicholson took great pains to consciously “un-Jack the part,” as he later told Playboy); the then-65-year-old actor channels what feels like a lifetime of pain, regret, wonder, and sorrow into this modern-day Prufrock. You get all of this, plus a priceless reaction shot to a very naked Kathy Bates entering a hot tub.

Meet Frank Costello, the boss of Boston’s underworld. He’s an Irish gangster and a fixture around the neighborhood, the kind who’ll buy groceries for a kid’s grandmother and shamelessly come on to your teenage daughter, because whaddaya gonna do? If the kingpin in Martin Scorsese’s Oscar-winning revamp of the Hong Kong crime thriller Infernal Affairs bears more than a passing resemblance to the notorious Whitey Bulger, it isn’t coincidental — the character is inspired by the real-life criminal. Nicholson didn’t want to play Costello like he was Bulger 2.0, however. Instead, he turned The Departed‘s villain into a Beantown Caligula, throwing fistfuls of cocaine around, waving a disembodied hand at Leonardo DiCaprio’s undercover cop, and brandishing a dildo at Matt Damon’s precinct mole. “I was looking for a bad guy,” he told Variety as to why he took the part, and Nicholson proceeded to turn this mobster into the baddest possible guy he could imagine. It’s a performance that’s almost too big for the movie to contain at times, hitting its over-the-top crescendo when Costello mentions “a rat” in the organization and makes a vermin-like facial expression. But it’s also a great last gasp of lunacy from the star; even though he’d make three more films before retiring, this crime thriller was really Jack’s swan song. Meeting a woman on the street, Costello inquires about her mother. She’s on her way out, she says. “We all are,” he replies. “Act accordingly.”