The Legendary Jack Nicholson’s 10 Best Roles

This was a tough one to put on here. On one hand, Jake is certainly one of the most iconic and memorable characters Jack Nicholson has played, but the fact that this is a Roman Polanski movie does make it awkward to celebrate.

Let’s not celebrate the movie, but instead just focus on what a great performance Jack Nicholson gives as a detective who ends up falling into one of the biggest corruption cases the city has ever seen! Add to this a rather interesting relationship with Faye Dunnaway’s Evelyn Cross. Jack plays the LA detective perfectly, it is such a believable performance that you feel like you are there with every step.

Look, I get that Anger Management may not make everyone’s 10 best Jack Nicholson roles list, but this is such a fun movie. Starring alongside Adam Sandler, Jack Nicholson plays the role of a doctor who is trying to help Adam Sandler’s Dave deal with his anger and other social and personal issues.

Adam Sandler and Jack Nicholson may not sound like an obvious pairing at first, but these two are fantastic together. It is so much fun getting to see Jack Nicholson get to be super crazy and unhinged, and he steals the show here and will have you cracking up throughout the movie. You know, Jack Nicholson truly has a great career, but the stuff he was doing in the 2000s was just as good as his earlier roles.

We are sticking with the early 2000s as we look at Jack Nicholson’s role as Jerry Black from the Sean Penn directed film, The Pledge. This is a forgotten and underappreciated movie that deserves way more love!

The Pledge is a thrilling and heartbreaking movie where Jerry Black promises a grieving mother that he will find the killer of her daughter. We are with him every step of the way, and we are committed to wanting him to succeed. There is a real vulnerability about Jerry Black in this movie that you don’t always get in a Jack Nicholson movie and that is what makes this role stand out so much. This is truly a great movie and one that everyone needs to check out.

Warren Schmidt is an unusual and fun role, so much so that you can tell Jack Nicholson had a ton of fun making this movie. Warren Schmidt is retired and widowed and he is having a hard time trying to adjust to his new life. He kind of goes off the rails, finds out some rough stuff about his wife, and even questions if his life ever mattered at all.

This is all wrapped up around these letters he sends to a little boy he is sponsoring in Tanzania! Oh, there is no way you can talk about About Schmidt without mentioning the hilarious scene with Warren and Kathy Bates’s Roberta! The fact that he can make you laugh and also break your heart shows what a great actor he truly is!

A Few Good Men has an absolutely stacked cast with the likes of Tom Cruise, Demi Moore, Keither Sutherland, Kevin Bacon, Kevin Pollak, and more. However, it’s the famous “You can’t handle the truth” line from Jack Nicholson’s Col. Nathan Jessop that people remember about this movie.

Jessop is pretty much the antagonist of this courtroom drama, where we find out that the ruthless colonel is willing to do whatever it takes to protect his military fiefdom. It’s a movie about morals and how far people are willing to go in order to stand up for what they believe in. This is a blockbuster performance from Jack Nicholson and it has to be one of his most quoted lines too!

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How can you have a list of the 10 best Jack Nicholson roles and not have The Shining on it? “Here’s Johnny!” is right up there with the quote we just discussed when it comes to iconic lines from Jack Nicholson.

His descent into madness as Jack Torrance is pure terror and while his performance is fantastic, we do also have to talk about Shelly Duvall (who sadly passed away around the time of this writing). Her reactions to the craziness of Jack truly cement just how off the deep end he has gone. His facial expressions, especially his eyes, make you think that this guy is legitimately crazy! You know a role is iconic when it gets parodied so many times and Jack Torrance has been parodied to death!

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This Martin Scorsese crime thriller is an absolute classic that boasts a blockbuster cast, all of whom are on top form. Jack Nicholson plays the role of Frank Costello, a mob boss in Boston who has one of his men infiltrate the Boston PD.

However, he also has a rat in his own crew. What is so great about Frank Costello is that he is as ruthless as you can get and the way he goes on about finding this rat is sheer terror. What’s great about this role is that we get to see just how dynamic an actor Jack Nicholson is as he can go from being calm and even charming to just downright psychotic. This is one of the all-time greats when it comes to crime thrillers. 

Next up we have a movie and a role that may not make many 10 best Jack Nicholson roles lists, but this is a real personal favorite that always makes me laugh. Jack Nicholson plays the role of Darryl Van Horne and he is best thought of as The Devil!

He is charming, but also quite vulgar, and three witches played by Michelle Pieffer, Susan Sarandon, and Cher all end up in a relationship with him. This is such a fun movie and the way that Darryl has a different relationship with each woman is so well done. He has fantastic chemistry with all three leading ladies and that shows what a great and versatile actor he is. This is easily one of his most amusing and underappreciated roles. It’s a real shame we never got a sequel to this as they certainly set it up for one.

Tim Burton’s Batman was a real game changer when it was released in 1989! The dark and brooding Michael Keaton needed a great foe to go against and who better than Jack Nicholson to play the role of The Joker? One of the interesting bits of trivia about this movie is that Jack Nicholson insisted on getting top billing – and to be fair, he deserved it.

Nicholson plays a dual role as we see him as Jack Napier before he becomes The Joker. One of the best and most underrated lines is his “My face on the one dollar bill”. Something interesting about this movie is that we get to see Keaton and Nicholson interact in every combination. You get Jack Napier and Batman, The Joker and Bruce Wayne, and of course, Batman and The Joker! I do also want to mention that the NES and the Sega Mega Drive/Genesis games that were made based on this movie are fantastic!

Surely (sorry for calling you Shirley) as you got closer and closer to the number 1 spot on my 10 best Jack Nicholson roles you had a thought that Randle McMurphy was going to be number one! This is an iconic movie in every sense of the word and for many people, one of the greatest movies ever made.

Jack Nicholson’s McMurphy ends up in a psychiatric hospital where he makes friends with the inmates and changes their lives, all the while butting heads with the deranged Nurse Ratched. The way Jack Nicholson brings the character to life and his various interactions with the other inmates, especially The Chief, is movie magic. The ending is one of the greatest of all time as it makes you sad for Randle, but happy for The Chief. One Flew Over The Cuckoo’s Nest is also amazingly parodied in The Simpson’s episode “Stark Raving Dad,” which makes for a great watch once One Flew Over The Cuckoo’s Nest has finished.

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