Jack Nicholson is, without a doubt, one of the most beloved actors of all time. With a career spanning over 40 years, Nicholson is one of the great icons of cinema with his blend of charisma and sardonic villainy.

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Though he has played almost every archetype in the book at one point or another, Nicholson is perhaps best known for his portrayals of the anti-hero. Oftentimes, he is able to make extremely flawed and heartless characters into likable leads in his films, a skill that has helped him nab numerous Academy Awards and other prestigious accolades.

Freddy Gale - The Crossing Guard (1995) - 75%

Nicholson's run in the 90s was the last great decade in the actor's storied career. Making more unconventional choices than ever, one of Nicholson's lesser-seen gems came in this era with The Crossing Guard.

The first of two collaborations with actor-turned-filmmaker Sean Penn, The Crossing Guard casts Nicholson as a man who spirals into alcoholism and depression after the death of his daughter in a drunk driving-related car accident. Ostensibly a mature and understated take on the "revenge drama" formula, Nicholson's pained performance elevates the material.

Daryl Van Horne - The Witches Of Eastwick (1987) - 76%

Jack Nicholson reclines on a bed from The Witches of Eastwick

Jack Nicholson seemed to be having a blast in the 80s. In that decade, he managed to score numerous hits and registered many of his most iconic performances.

That being said, Nicholson has rarely seemed to be having as much wicked fun as he did as the antagonist in The Witches of Eastwick. As a literal "Devil-in-Disguise," Nicholson inserts himself in the lives of three witches, first by seducing them, then opposing them. He brings his malicious wit to the part, making it one of his more entertaining roles.

Jerry Black - The Pledge (2001) - 78%

Jack Nicholson The Pledge - Good Actors Bad Movies

Once again, Sean Penn and Nicholson collaborated on this gritty crime thriller. In many ways a thematic sibling to The Crossing Guard, the pair revisit themes of obsession and death. Nicholson plays Jerry Black, a freshly retired detective who continues to pursue a child murderer after promising the parents of one of the victims that he would find the killer.

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Eschewing the typical tropes of the "whodunnit," the film instead focuses on the damaging effects of not letting go of an investigation, a tricky balancing act that pans out thanks to Nicholson's subtle and complex performance.

Jack Torrance - The Shining (1980) - 84%

Jack Nicholson in The Shining

One of the most revered and debated horror films ever made, Stanley Kubrick's The Shining is one of cinema's great depictions of a descent into madness.

At the heart of it all is Nicholson as writer Jack Torrance, a man who takes his wife and son to an infamous hotel to act as an off-season caretaker. Nicholson's genuinely terrifying portrayal of Torrance's slow spiral into completely unhinged lunacy is a performance of great pace and restraint and has since become one of his signature roles.

Charley Partanna - Prizzi's Honor (1985) - 86%

Charley and Irene talking in Prizzis Honor

One of Nicholson's best comedic turns, Prizzi's Honor marked another great entry in the actor's span of films from the 1980s. The film, which is directed by master auteur John Huston, tells the intriguing story of a mafioso hitman who falls in love with a rival, played by Kathleen Turner.

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The chemistry between the two is unique and it guides the film's biting and pessimistic script with aplomb. One of Huston's final films, Prizzi's Honor is underrated and one of the funniest movies of the decade.

Jonathan - Carnal Knowledge (1971) - 87%

Jack Nicholson leaning on a wall talking to someone in Carnal Knowledge

Mike Nichols sought to probe the sexual mentality of the American male with this 1971 minor masterpiece. Nicholson stars alongside Art Garfunkel as two collegiate friends who take very different romantic paths in life after intertwining freshman year. The characters are juxtaposed in such a way that the film tries to expose the contradictory logic of the male libido.

Nicholson's Jonathan is the more aggressive and unlikable of the two, though he is able to bring an expected amount of nuance and gravitas to the role, making it one of his better mid-career showings.

Robert Eroica Dupea - Five Easy Pieces (1970) - 88%

Jack Nicholson in Five Easy Pieces

Nicholson's first iconic leading performance in a classic film came in this 1970 melancholic drama about a troubled piano prodigy who decides to be a construction worker and live a blue-collar life. After returning home to see his highfalutin family, old wounds are opened up.

Nicholson's Dupea is a character rife with angst and genius, a combustible combo that rears its head most prominently in the film's legendary diner scene. In many ways, this film would set the pedigree for the rest of Nicholson's incredible run in the 1970s.

Buddusky - The Last Detail (1973) - 89%

Jack Nicholson in The Last Detail

The Last Detail is not as well known as Nicholson's biggest roles, but it is one of his very best. Channeling a mix of heart and as the ultimate bad influence, Nicholson stars as one of two naval officers charged with escorting a young private to the military prison where he has been sentenced to spend time.

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Nicholson's Buddusky decides to give the young offender a condensed amount of life experiences on the way, including sex and drinking. Buddusky is one of Nicholson's best hot-head characters, best exemplified in the scene where he tries to order the kid a beer.

Randle P. McMurphy - One Flew Over The Cuckoo's Nest (1975) - 94%

Jack Nicholson in One Flew Over the Cuckoos Nest

Truly one of the greatest male performances in one of the greatest American films ever made, Nicholson's Randle McMurphy is one for the ages. After being committed to a mental asylum, McMurphy inspires dissension among his fellow in-patients against the tyrannical eye of Nurse Ratched.

Nicholson creates one of the great anti-heroes here as a man who is as infinitely flawed as he is likable. The film's genius script gives Nicholson the perfect fodder to unleash what might arguably be his most famous performance of all time.

J.J. Gittes - Chinatown (1974) - 99%

Jack Nicholson in Chinatown

Nicholson resurrects the noir detective in Roman Polanski's thriller classic Chinatown. He plays hard-boiled private investigator J.J. Gittes, a rough-around-the-edges man with a heart of gold who gets in way over his head once he is hired to investigate a case of adultery.

Once the film picks up its pace, Nicholson guides the audience through a murky swamp of lies and danger. Alternately steamy, suspenseful, funny, and caustic, Polanski and Nicholson create a thoroughly entertaining addition to the noir canon and one of the best films of the 70s and their respective careers.

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