Jack Nicholson’s Top 10 Grittiest Roles

Roman Polanski’s Chinatown—an essential work in the era of New Hollywood cinemamarked by experimental direction, non-linear narratives, unresolved endings—turns 40 this Friday. To celebrate this renowned masterpiece from one of the great directors of the film school generation, we took a look back at Jack Nicholson’s filmography and curated his darkest, creepiest, and sometimes most terrifying roles to date.

Nicholson has never been one to shy away from roles of onion-like complexity. Even his more comedic roles share an underlying tone of sardonic abrasiveness. Nicholson is a product of New Hollywood cinema and his career epitomizes the late 1960’s to mid-1980’s off-the-wall experimentation in efforts to break away from the studio system altogether and try to go about making films in a different way. Nicholson’s characters were often faulted, broken, and challenging for viewers to categorize as either good or bad, black or white. Yet, they all seem to fall under the umbrella of “gritty,” so in honor of Chinatown‘s b-day, here’s a look at the beloved actor’s top 10 grittiest roles.

10. George Hanson – Easy Rider (1969)

When we first meet George, he’s sleeping off his hangover in the town’s jail. He’s dirty, disheveled, and dying for the hair of the dog that bit him the night before. One flash of his lawyer’s license, and he’s on his merry way to join Wyatt and Billy on their road trip. While Hanson was without a doubt the wildcard of the group, through his drunken fog he was actually the most insightful – “This used to be a great country,” he mused before being bludgeoned to death in his sleep.

Easy Rider is available to stream on Netflix. 

9. Frank Chambers – The Postman Always Rings Twice – (1981)

Chambers, a hapless drifter, catches the eye of lowly Cora (Jessica Lange) who is desperate to get out of her loveless marriage and make a life of her own. Chambers just wants some stability in his life and Lange was super hot in the 80’s, so of course when she proposed they kill her husband and run away together, Chambers was all for it. Of course, their bad karma came back to bite them in the end, but Nicholson really embraced the dark, sexy side of him in this steamy noir-like thriller.

The Postman Always Rings Twice is available for rental on Amazon Instant Video and iTunes. 

8. Henry Lloyd Moon – Goin’ South (1978)

Sentenced to death by hanging after recklessly robbing banks and pissing off the local townfolk, Moon is saved by Julia (Mary Steenburgen) who s agrees to marry him and take responsibility for his poor behavior (Yes, four people wrote this movie and they came up with that plot device). But with a combination of the criminal lifestyle he can’t bear to leave behind, the scruffy grizzly beard, and the spot-on spitting – ptooey! – into perfectly scattered tin bowls throughout the entire movie, Nicholson’s role as Moon definitely makes the grit list. Just look at the poster:

Goin’ South is available to stream on Amazon Instant Video and iTunes.

7. James “Jimmy” Hoffa – Hoffa (1992)

The movie kind of stunk—sorry Danny DeVito, you’re a better actor than a director—but Nicholson managed to come through once again, playing the most notorious union boss in history. Thinking about it now, it’s hard to imagine anyone else in that role without it being a total bomb. Plus, it was great practice for when he took on the role of Frank Costello in The Departedover a decade later.

Hoffa is available for rental on Amazon Instant Video and iTunes.

6. J.J. “Jake” Grittes – Chinatown (1974)

A hard-as-nails detective who’s “Just trying to make an honest living,” despite what some of the locals may say, Jake gets in too deep with corrupt clients while trying to solve a case. Unfortunately for him, he ends up unravelling a conspiracy that’s effecting the entire city. Nicholson pays incredible homage to cinema’s hardboiled crime detectives who came before him and gives us one of his most memorable performances to date.

Chinatown is available to stream on Netflix. 

5. Will Randall – Wolf (1994)

After being wronged his entire adulthood, Will snaps after he’s bitten by a wolf, unveiling his inner id and forcing him to go after those who have betrayed him. It isn’t long after Will’s transition that you might realize how often Nicholson bares his teeth in just about every role he plays.

Wolf is available to stream on Amazon Instant Video. 

4. Randle Patrick “R.P.” McMurphy – One Flew Over the Cuckoo’s Nest (1975)

Taking on a role like McMurphy could make or break an actor’s career. Playing a rapist who snakes his way into a mental institution in order to avoid jail would probably cause some actors to push the script back across the table to the producer, but not Jack. He made McMurphy the most lovable, wannabe psycho of all-time, especially after he choked out the evil Nurse Ratched.

One Flew Over the Cuckoo’s Nest is available for rental on Amazon Instant Video andiTunes. 

3. The Joker/Jack Napier – Batman (1989)

The voice, the makeup, the one-liners, the psychotic laughter – we couldn’t get enough! And to think David Bowie, Willem Dafoe, or Robin Williams almost had the role. Nicholson accepted creator Bob Kane’s three-year-long plea to play the part under one condition – he wanted it in his contract that he would be granted time off to catch L.A. Lakers games. No, he wasn’t joking.

Batman is available for rental on Amazon Instant Video and iTunes.

2. Frank Costello – The Departed (2006)

A fictitious embodiment of ruthless gangster Whitey Bolger, Nicholoson owned the role of mob boss Frank Costello. That image of him maniacally laughing and grinning through bloody teeth after he’s been shot by crooked cop Colin Sullivan (Matt Damon) is so unsettling and creepy, he probably even spooked Scorsese who has directed enough brutality for a lifetime.

The Departed is available for rental on Amazon Instant Video and iTunes.

1. Jack Torrance – The Shining (1980)

What makes the character of Jack Torrance so intriguing is that you find yourself nervously giggling at the most disturbing sequences. He’s terrifying in the way he smiles and moves – gliding through the ballroom, slowly creeping up the stairs after Wendy, shouting and growling after Danny as he chases him through the maze. However, Nicholson gives it that twist of his and suddenly, it becomes some of the darkest comedy you’ll ever see in horror and gives “villain” a whole new meaning. Mr. Nicholson, you are one demented genius to be able to bring out these clashing emotions in people, that’s for sure.

The Shining is available for rental on Amazon Instant Video and iTunes (But you should totally just buy it).