Top 20 Greatest Roles of Jack Nicholson

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No. 20 - How Do You Know

No. 20 - How Do You Know

Jack played Charles Madison in this comedic movie starring Owen Wilson and Paul Rudd. Madison is in trouble with the law and puts all of it on his son, played by Rudd. He can either face the music and take his dad’s place or potentially find a way to rat him out. Jack was hilarious in this movie and brilliant with comedic timing and overall delivery.

No. 19 - Ironweed

No. 19 - Ironweed

Playing a washed up baseball player named Francis Phelan, Jack was able to translate well into the romantic drama category with his role in Ironweed. Phelan deserted his family in the 1910s after he dropped his baby boy, resulting in the death of the child. From then on, he was a bum always punishing himself. He later meets Helen Archer played by Meryl Streep, who becomes his lover and drinking companion. Despite making a little over 7 million at the box office in 1987, many critics give the movie a positive review. So it’s worth checking out for sure.

No. 18 - Reds

No. 18 - Reds

Playing playright and hidden activist Eugene O'Neill, Jack was nominated for several awards for his role in this film. While it is not as well-known as many of his other movies, it is considered to be an excellent movie for war movie fans as well as fans of activism. It was a major film for its time due to recent wars and national problems. So the performances had to be spot on to avoid a letdown. Jack played his character well and many feel he was the best part of the movie.

No. 17 - Hoffa

No. 17 - Hoffa

Playing the title character of Jimmy Hoffa, Jack does an amazing job worthy of awards despite the movie failing somewhat. He did not win one, but was nominated for a Golden Globe. He was also nominated for a Golden Raspberry Award for Worst Actor. This made him one of the only people to get nominated for worst actor and best for the same movie from two different award ceremonies.

No. 16 - Five Easy Pieces

No. 16 - Five Easy Pieces

Jack plays Bobby Dupea in this 1970 drama film. Dupea is an oil field worker who also comes from a very musical family that he tells no one about originally. He ends up quitting his job and leaving for Los Angeles. Things get very interesting along the way and once they arrive. Jack does a great job in this movie, and so much so he was nominated for several awards, a Golden Globe and Oscar for Best Actor just to name a few. The movie ended up doing okay at the box office, but has since become a bit of a cult classic.

No. 15 - Anger Management

No. 15 - Anger Management

When playing Dr. Buddy Rydell, Jack was able to really translate into a comedic role that he wasn’t always known for. Adam Sandler is a known genius with his comedy movies that he helps to write and produce himself. Jack being part of one of those got many excited and he exceeded all expectations going in. He was hilarious playing the anger management doctor to Sandler’s character. But understand, Buddy was not the type of doctor that most of us think about. He ends up taking Sandler’s girlfriend from him all to help teach him a lesson that ends up with him getting married. Makes no sense you say? See the movie and you’ll get it!

No. 14 - Easy Rider

No. 14 - Easy Rider

Playing George Hanson, Jack plays a lawyer and local drunk who gets manipulated into trying marijuana and gets hooked to it. The movie was possibly Jack’s first major success, and the movie was a wild success at the box office as well in 1969. This seems to be the movie where the trademark sunglasses really started for Jack. Jack ended up getting nominated for several awards, including an Oscar.

No. 13 - Terms of Endearment

No. 13 - Terms of Endearment

Originally penciled in to be played by Burt Reynolds, Jack played Garrett Breedlove in this Hollywood classic. In a sea of stacked talent, Jack was able to stand above everyone in the movie to be nominated for awards. He won every award he was nominated for, including the Oscar for Best Supporting Actor.

No. 12 - The Bucket List

No. 12 - The Bucket List

Coming to the end of his life, Jack’s character Edward Cole meets Carter Chambers played by Morgan Freeman. The two realize that their lives are coming to an end very soon after getting startling health results. The two want to end life on a bang, and decide to do everything on their Bucket List. The movie proved Jack still had it in 2007 when the movie hit theaters. It was a moving, comedic, and overall terrific movie starring two of Hollywood’s best.

No. 11 - Prizzi's Horror

No. 11 - Prizzi's Horror

Playing Charley Partanna, Jack puts on another classic performance as a hit man who tends to only get his hands dirty when he absolutely has to. Jack won several award for his role both foreign and domestic and was even nominated for an Oscar.

No. 10 - About Schmidt

No. 10 - About Schmidt

Playing Warren Schmidt, Jack does an absolutely amazing job playing a man who goes into retirement and simply hates it. He wants to find better things to do, and his adjustment to his new life seems to really be trying on him. The movie follows how he gets his barrings, and it is quite worthy of the hype it has gotten from critics. Nominated and winning numerous awards, Jack’s performance was magic in this movie. It was highly worthy of the top 10 in my book.

No. 9 - Something's Gotta Give

No. 9 - Something's Gotta Give

In 2003, most felt that Jack was done as a leading man in Hollywood. He proved them wrong when he played Harry Sanborn in this romantic comedy opposite Diane Keaton who also excelled in this movie. Harry is a music mogul who was actually dating the daughter of Keaton’s character when the two met. He has some heart trouble and ends up staying with Keaton’s character, and although confusing when written down it ends up being a hilarious situation. The two are excellent in this movie. Jack was nominated for a Golden Globe for his performance, and despite not winning, this will go down as a Jack classic that the whole family can enjoy. It’s one that guys will be happy to watch with girlfriends. I guarantee it.

No. 8 - The Last Detail

No. 8 - The Last Detail

Playing Navy man Billy Buddusky, The Last Detail was considered a success in 1973 despite grossing just 10 million at the box office. For a 2.5 million dollar budget, it was a financial success for the studio. Jack was nominated for a Golden Globe and Oscar yet did not win. Most feel that this is one of Jack’s best movies, but one that few people see due to the age and lack of popularity.

No. 7 - Chinatown

No. 7 - Chinatown

Jack plays Jake Gittes, a private detective in this psychological thriller. The movie only drew 24 million in 1974, but while today that seems meager, that would be a terrific number then. This is especially true, with a budget of only 6 million. Jack was nominated for several awards and ended up winning the Golden Globe for Best Actor. He was nominated, but did not win the Oscar for his performance.

No. 6 - The Departed

No. 6 - The Departed

Considered one of the best mob movies of all time, this movie is stacked with great American actors. Jack Nicholson plays Frank Costello who happens to be an Irish mob boss who leads everyone astray but also into money. The movie was a wild success and even Best Picture at the Oscars. Nicholson was a supporting actor in this movie and not the main focus. But he was an excellent addition to it and made the movie better for it.

No. 5 - As Good as it Gets

No. 5 - As Good as it Gets

In one of Jack’s best performances, he plays an OCD author named Melvin Udall. He does everything the same, and the question is asked: “Is this as good as it gets?” The movie was beloved by people, and did quite well at the box office. Jack won an Oscar for this role, and most feel it could be his best acting performance in any movie he was involved with.

No. 4 - Batman

No. 4 - Batman

Other than Heath Ledger, Jack Nicholson’s Joker character may be the best villain performance in any superhero movie. He was nominated for several awards with this movie, and at a time when Superhero movies weren’t the main focus of Hollywood film makers. The movie grossed millions and was a blueprint for how superhero movies should be made at the time. No Batman movie surpassed it until The Dark Knight by Chris Nolan. Jack’s performance as The Joker however, is legendary.

No. 3 - The Shining

No. 3 - The Shining

Here’s Johnny! Crazy, psychotic, all names you could call Jack Nicholson’s character Jack Torrance in this movie. As great as a movie as this is, and one that we think of when we think of a Nicolson classic, the movie was not as big of a success as we think. Jack was also not nominated for any award. But he was fantastic in the movie.

No. 2 - One Flew Over the Cuckoo's Nest

No. 2 - One Flew Over the Cuckoo's Nest

Considered a massive box office success, this dramatic movie made in 1975 could be Nicholson’s breakout role in Hollywood. Randle McMurphy played by Jack, is a criminal who served a short sentence for rape that wants to avoid hard labor, so he fakes being mental unstable so he can spend the rest of his sentence at a mental institute to avoid the labor. Once he gets to the mental institute, things get nuts from there. Excuse the pun. Jack won Best Actor at the Oscars for his role as well as numerous other awards. Many put this movie in their top 50, and rightfully so. It is amazing.

No. 1 - A Few Good Men

No. 1 - A Few Good Men

I can’t handle the truth, that’s for darn sure. While Jack was not the main character in this movie, he was a major part of it as Colonel Jessep. His performance helped him get nominated for just about every award possible. Despite him not being the main character, A Few Good Men is one that most of us think of as a Jack Nicholson classic.

Jack Nicholson has been nominated for an Oscar over 10 times and won 3 in his illustrious career in American cinema. His movies have been considered legendary, cult classics, and crazy exciting. No matter the response, they were always memorable. Here is a countdown of the top 20 movies Jack blessed us with. Enjoy0