ByJust Good Movies, writer at
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Like so many contemporary Hollywood greats, Jack Nicholson started his career under the guidance of B-movie legend Roger Corman. After about a decade of acting in various exploitation films and minor flirtations with mainstream Hollywood, Nicholson wrote The Trip, a psychedelic LSD fuelled movie, produced and directed by Corman and starring Peter Fonda and Dennis Hopper. This clearly laid the foundations for Nicholson's breakthrough into the mainstream when he appeared alongside Fonda and Hopper in 1969's Easy Rider, a movie which can be seen as the true start of the New Hollywood period for which Nicholson basically became the poster child. His maniacal non-conformist and anti-hero-like qualities made him perfect for the period and it's these very same qualities which have defined the man's 65-year long career, which has earned him the most Oscar nominations for any male actor ever (twelve) and a tie for most wins with Daniel Day-Lewis and Walter Brennan as all three men have three statues to their name.

Prizzi's Honor (Huston, 1985)

Whilst the two had acted together in 1974's Chinatown (I'll get to that one later), it wasn't until 1985 that Nicholson starred in Prizzi's Honor, the final last film by one of Hollywood greatest directors and sometimes actor, John Huston. His portrayal of a not too smart and matter-of-fact mob hit man was without a doubt one of the strongest suits in this pitch-black comedy. Not Nicholson's nor Huston's best film, Prizzi's Honor is well worth checking out for fans of either Hollywood legend.

As Good as it Gets (Brooks, 1997)

Perfect casting would have contributed greatly to Nicholson's second Academy Award win for Best Actor here. Playing a dysfunctional narky misanthropic novelist who is suffering from a obsessive-compulsive disorder to boot, it is hard to imagine any other actor having been able to nail this part so perfectly. Add to that a film that balances drama, comedy and romance effortlessly and you end up with the most light-hearted entry in this top ten list. And who wouldn't want to see a cynical and grumpy Nicholson interact with a waitress, a homosexual artist and a little lapdog?

About Schmidt (Payne, 2002)

In the year that Nicholson turned 65 in real life, he starred in the age appropriate role of Warren Schmidt, a bitter man who has just retired, loses his wife shortly afterward and seeks purpose in a life, which he feels he has wasted and that has not mattered to anyone around him. In one of Nicholson's most controlled performances, he also manages to give one of his career's best. A poignant character study of man who at the end of his life realizes how empty the experience has been all along.

The Departed (Scorsese, 2006)

In the film that finally gave Martin Scorsese his coveted Best Director and Best Picture Academy Awards, Jack Nicholson turned in one hell of a performance as the menacing and ruthless Irish gangster Frank Costello, who as a result of a suggestion by the actor himself ended up being based on real-life mobster and informer Whitey Bulger. In a film stuffed with impressive performances, Nicholson nearly stole the show with his truly frightening portrayal of the gangster. And now that I have your attention: if you have never seen the Hong Kong classic Infernal Affairs, which The Departed is based on, change your plans tonight and simply right that wrong.

Easy Rider (Hopper, 1969)

An independently produced biker movie which nonetheless became a monumental film as it gave a voice to the sixties' counterculture, gave Nicholson his real breakthrough (and his first Oscar nomination) and truly announced the arrival of the Hollywood New Wave, a movement which would rule American cinema throughout the seventies. In a twist of fate, Nicholson scored the pivotal role of a drunk lawyer when Rip Torn, a Texan actor who the role was originally written for, almost came to blows with director Dennis Hopper after he expressed his dislike for rednecks, which he encountered whilst scouting locations for the movie in the South. Nicholson managed to make his minor role stand-out and the rest is history.

The Last Detail (Ashby, 1973)

Nicholson was quick to capitalize on his new found success through Easy Rider and quickly became the face of the New Hollywood movement with some true classics of the era, The Last Detail being one of them. Playing “Badass” Buddusky, one of two Navy men escorting a young sailor to jail for a minor crime, Nicholson received his third Academy Award nomination for Best Actor here. Playing the role of a subversive non-conformist with verve and that trademark smirk, Nicholson's character convinces his partner that they have to use the week they have to show the young goodhearted sailor a great time before he starts his lengthy sentence and wastes the most important years of his life. Notable for its incessant curing at the time, the studio decided to only give The Last Detail a wide release after Nicholson was awarded Best Actor at Cannes.

Five Easy Pieces (Rafelson, 1970)

Another New Hollywood classic and another Best Actor nomination at the Academy Awards for Nicholson, Five Easy Pieces is the film in which the actor really cemented his hold on the non-conformist role. Playing Bobby Dupea, a man from a wealthy family who was poised to become a well respected concert pianist but turns his back on his family and upbringing, Nicholson gave a towering performance as an alienated individual who is mad at the entire world and is looking for more meaning in his life. Watch out for the scene where he fights with a waitress at a diner over a chicken salad sandwich; it is pure gold.

The Shining (Kubrick, 1980)

Nicholson's ability to play intense maniacal characters has maybe never been put to better use than when he played Jack Torrance in Stanley Kubrick's horror masterpiece The Shining. Stephen King, the author of the novel the film is based on, although the two differ significantly, objected to Nicholson's casting as he felt the actor's previous roles would give away immediately that the character would go insane. On top of that it has been widely documented that King despised the final film in its entirety. Clearly King knows a lot more about writing than he does about filmmaking as The Shining is now widely considered as one of the best horror films of all time and Nicholson's performance in it as pitch perfect. “Heeeere's Johnny!”

One Flew Over the Cuckoo's Nest (Forman, 1975)

If the New Hollywood films of the early seventies made Nicholson into a respected and successful actor, One Flew Over the Cuckoo's Nest was the film that truly turned him into a bona fide movie star in the mid-seventies. Finally winning the Oscar for Best Actor, after having been nominated for it three times previously in the four years leading up to this win, Nicholson's stunning portrayal a free-spirited man who feigns insanity in order to avoid jail time and ends up in an mental hospital instead was a true tour-de-force performance. One Flew Over the Cuckoo's Nest is only one of three films in the history of the Academy Awards to win all five major awards (Best Film, Director, Screenplay, Actor and Actress). An undeniable classic of American cinema and one of Nicholson's most iconic roles.

Chinatown (Polanski, 1974)

The top three films in this list are basically interchangeable as all of them are masterpieces in their own right but Roman Polanski's Chinatown, his last film made in the United States and arguably the best neo-noir ever committed to celluloid, is my top pick, if only because nowadays it seems to be slightly less known amongst the general public than the two previous entries. Nicholson gives a stunning take on the character of a smart-ass private investigator who is in over his head, a role which would have been played by Humphrey Bogart had this movie been actually made in the forties. All other elements of the film just come together perfectly, with special mention of the screenplay by Robert Towne, which has become the stuff of legend amongst screenwriters. If you have never seen Chinatown do yourself a favour and get onto that. You won't regret it.

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