The career of Jack Nicholson is certainly an impressive one. He has appeared in 62 films, with a long list of incredibly successful features to his name. Obviously, it was the 70s and 80s that saw him at his finest, but he still managed some stellar performances in his later years, mostly avoiding the strange low-budget comedy many classic actors wind up appearing in as their career fades.
Nicholson claims to be retired now, having not appeared in a film since 2010’s How Do You Know. We’ve used IMDB to rank the five best films he has ever had a prominent role in, and have compared those to the five worst.
BEST: One Flew Over The Cuckoo’s Nest (8.7)
Often considered one of the greatest films in history, it is no surprise that One Flew Over The Cuckoo’s Nest comes in at the top of our list. Nicholson gives one of the most impressive acting performances ever as he brings Randall McMurphy to life.
There is a certain mystery around whether McMurphy is as crazy as he claims, or whether he is actually pretending as the audience is led to believe. This sounds like a near-impossible characterization to pull off, but Nicholson somehow nails every second he is on screen. Mixing comedy with emotion and mystery, this truly is one of the single greatest acting performances ever.
WORST: The Cry Baby Killer (5.1)
Most classic actors end up stuck in a loop of terrible comedies or role-reversing dramas in which they’re no longer the bad guy by the time their career is coming to a close. Somehow, Jack Nicholson avoided this, and it is, in fact, his first film ever that ended up his fifth worst-rated film on IMDB.
He plays a seventeen-year-old, scared that he has just committed manslaughter, who decides, for some reason, his best bet is to take loads of people hostage... The Cry Baby Killer is a crime drama, pretty much only notable for being Nicholson’s first role. In fact, it was out of print until 2006.
BEST: The Departed (8.5)
The fourth-to-last film Nicholson (potentially ever) starred in was 2006’s Martin Scorsese blockbuster, The Departed. Combining the talents of Leonard DiCaprio, Matt Damon, Mark Wahlberg and Nicholson himself in the four starring roles was pretty much-guaranteed success, but the response was better than anyone could have predicted. It’s literally ranked higher than The Shining on IMDB!
Nicholson plays mob boss Frank Costello with incredible poise, drawing on the crazed persona of many of his past parts while combining it with something new that made its way into his style in his later years.
WORST: The Terror (5.0)
Seventeen years before Jack Nicholson dominated the horror world through his incredible, commanding presence in The Shining, he appeared in 1963’s The Terror.
An independent grindhouse horror with a limited release, it was a stretch from the sort of thing Nicholson would be appearing in in years to come. He plays a Napoleon soldier who gets lost and soon encounters a shapeshifting devil.
BEST: The Shining (8.4)
Stephen King may have hated it, but it’s still one of the most impressive feats in the history of cinema. Stanley Kubrick gave Nicholson the reigns to make the character of Jack Torrance his own, basically creating every trope in the book for the crazy horror-film guy.
Not only did he improvise the film’s most iconic line, “here’s Johnny!”, but the film includes one of the most powerful, disturbing and intense scenes in horror history: “Wendy, darling, light of my life, I’m not gonna hurt you. I’m just gonna bash your brains in.”
WORST: Man Trouble (4.7)
You can sort of tell from the title that Man Trouble was never going to be a world-dominating success, and instead, a pretty well-despised rom-com.
Despite coming out in the same year as A Few Good Men and being created by the same people who made the well-loved, Nicholson-starring Five Easy Pieces back in 1970, this film didn’t land on its feet. Many critics felt that Nicholson had been let down by the film and that viewers had only been drawn in due to Nicholson’s involvement.
BEST: Chinatown (8.2)
Coming a year before Nicholson achieved worldwide adoration for One Flew Over The Cuckoo’s Nest, Chinatown was released. It saw Nicholson team up with Faye Dunaway in an impressive performance that was nominated for an incredible eleven Oscars.
Nicholson’s ability to portray private investigator JJ Gittes and then turn everything on its head with the reveal of that twist at the end is seriously impressive stuff, though he obviously wasn’t able to keep the character alive after the film. The 1990 sequel The Two Jakes was nothing in comparison to its predecessor.
WORST: The Wild Ride (4.4)
Just Nicholson’s third film, The Wild Ride looks pretty... interesting... just from its poster. The film was never exactly intended to be a major hit, running at almost an hour and having entered public domain a long time ago, it has effectively been forgotten about by all except those who consider it a cult classic.
The re-cut version of the film turns itself into a long flashback, but Nicholson obviously wanted no more involvement with it. As such, an impressionist took on the role of an aging version of his character, Johnny Varron.
BEST: A Few Good Men (7.7)
Combining Jack Nicholson with Tom Cruise and Demi Moore seems like a rather strange combination. However, Rob Reiner (also responsible for Misery and Spinal Tap) somehow made it work.
Nicholson plays Colonel Nathan Jessup, a military colonel trying to figure out a response to the charges of murder faced by two marines. His self-important monologue that comes towards the end of the film is its highlight, demonstrating his incredible range as an actor.
WORST: The Rebel Ros (3.9)
At just a 3.9, The Rebel Ros is the lowest-ranked film on IMDB to give Jack Nicholson an important role. He plays the character of Bunny, who is strangely similar to a couple of other characters Nicholson played during a similar time period in films also about motorcycle gangs.
This one has a storyline that doesn’t exactly hold up these days: a motorcycle gang have a drag race to see who can ‘win’ a pregnant girl...
