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Jack Nicholson's 10 best films ranked in order of greatness

“Acting is everybody’s favourite second job.” – Jack Nicholson 

One of the 20th-century’s most iconic actors – and one of the most celebrated ever to walk the silver screen – the reverberations from Jack Nicholson’s remarkable career are still felt to this day. Now retired from filmmaking, Nicholson’s roles as madman Jack Torrance in Stanley Kubrick’s The Shining, and as R.P. McMurphy in One Flew Over the Cuckoo’s Nest remain some of cinema’s most revered characters. 

A bold, counter-cultural figurehead of cinema, Nicholson earned a joint record of 12 Oscar nominations, winning three, yet fascinatingly his legacy remembers him as an individual on the periphery of the industry as an ever eclectic creative. Look no further than his breakout role in Dennis Hopper’s Easy Rider as an eccentric dope-smoking lawyer, bridging the gap between the stiff establishment, and progressive liberalism.

Establishing himself a ‘bad boy’ image, Jack Nicholson would shape a career of great success from independent features to large Hollywood projects. Here, let’s take a look at his very best films…

The 10 best Jack Nicholson films:

10. Batman (Tim Burton – 1989)

“Never Rub Another Man’s Rhubarb.”

Jack Nicholson’s Joker certainly ranks among the most sinister depictions of Batman’s greatest villains, becoming a resident of the uncanny valley with his permanent wry grin.

Tim Burton’s tale of the Dark Knight of Gotham City, brings the Joker to the forefront of the story, pinning him for the first time in Batman filmography, toe-to-toe with the titular hero. Taking partly from the campy villains of the classic 1960s series, Nicholson brings a creepy sincerity to the spiked comedic role of the Joker, elevating Burton’s otherwise forgettable superhero caper. 

9. About Schmidt (Alexander Payne – 2003)

Morphing into an entirely different enigma toward the end of his career, Warren Schmidt is a more quiet and subdued version of Nicholson’s previously wild self. 

Adapted from the novel by Louis Begley, Alexander Payne’s 2003 follows Nicholson in a leading role as a recently retired man journeying across America to attend his estranged daughter’s wedding. It’s a far more grounded role than Nicholson is used to, but one which he embraces with open arms, revealing the scars and aching humanity of a broken man.

8. Terms of Endearment (James L. Brooks – 1983)

Oscar-darling Terms of Endearment won five awards in total during the 1983 Academy Awards, including Best Picture, Best Actress for Shirley MacLaine, and Nicholson’s first in a supporting role. 

Making the most of his limited screen time, Nicholson floats in and out of James L.Brooks’ film, based on the novel by Larry McMurtry which follows a Southern American family and the troubles of a widow looking for love. The poignant dramatic comedy centres around a core mother/daughter relationship, but is given spice by Nicholson’s astronaut-next-door who brings his trademark charisma to this American classic.

7. Easy Rider (Dennis Hopper – 1969)

Kickstarting an independent American film counterculture, Dennis Hopper’s revolutionary Easy Rider features Jack Nicholson as a suave wise-cracking traveller. Safe to say it’s an effortless performance. 

The influential film follows two drug-smuggling bikers (Peter Fonda and Dennis Hopper) heading from Los Angeles to New Orleans through the open roads of the desert landscape, meeting wild characters on-route. One of these characters is Nicholson, a lawyer with particularly laid-back sensibilities who bridges the gap between the establishment the two bikers hate and the counterculture they embrace. He is perhaps the film’s most memorable aspect.  

“I think I’ll order kidneys, ’cause I left mine out there on the road somewhere.

6. The Passenger (Michelangelo Antonioni – 1975)

From filmmaking force Michelangelo Antonioni, director of L’Avventura and Blowup, Nicholson once again reels in his eccentric self to bring a softened lead performance to The Passenger.

The neo-noir drama follows David Locke (Nicholson), an American journalist who unknowingly takes the identity of a dead arms dealer whilst trying to reach a civil war he is unable to find in Chad. Famous for the seven-minute-long tracking shot which concludes the film, Nicholson’s cool performance gives the steady film some enthusiastic life and a memorable sense of style. 

5. The Departed (Martin Scorsese – 2006)

Martin Scorsese’s 21st-century crime masterpiece, adapted from Alan Mak and Felix Chong’s Hong Kong thriller, bought an incredible ensemble cast together for a sharp tale of cat and mouse.

Finally winning the iconic director his own elusive Best Picture win, Scorsese’s The Departed follows an undercover cop in an Irish gang in Boston, and a mole in the police force who are both attempting to identify each other. It’s an ingenious plot that packs an explosive final punch with help from the performance of Nicholson as mob boss Frank Costello, clearly relishing his intimidating character with a delightfully menacing performance. 

4. Five Easy Pieces (Bob Rafelson – 1971)

The celebrated road movie Five Easy Pieces from Bob Rafelson remains among Jack Nicholson’s most memorable performances, helped by a particularly iconic dinner scene.

Playing an ill-tempered high-school dropout who picks up work on an oil rig in between a life floating through bars and motels, Nicholson’s raging Robert Dupea visits home to see his dying father. Earning four Oscar nominations including best picture and Nicholson’s first inclusion as best actor, Five Easy Pieces is a riveting drama set in the backdrop of a conflicted Nixon-led America, headed by an exhilarating lead performance.

3. Chinatown (Roman Polanski – 1974)

“Forget it, Jake. It’s Chinatown.”

A late neo-noir masterpiece from Roman Polanski puts Jack Nicholson at the forefront of its compelling narrative dealing with the deceit and corruption of 1930s L.A.

Winning an Oscar for Best Original Screenplay, Robert Towne’s script is truly spellbinding, following a private detective (Nicholson) who’s hired to expose an adulterer though is forced to face the strange wrongdoings of the city’s people along the way. Receiving a nomination himself for his leading role, Nicholson relishes Towne’s gorgeous dialogue to provide an enigmatic performance layered with mystery and dread. 

2. One Flew Over the Cuckoo’s Nest (Miloš Forman – 1975)

Among his most iconic film roles and embodying the character of the actor himself, Jack Nicholson’s role in One Flew Over the Cuckoo’s Nest is a monumental achievement and one that would almost single-handedly earn the film best picture at the Academy Awards. 

Nicholson plays Randle McMurphy, an anti-hero and criminal who pleads insanity and helps to rally the patients of the Oregon State Mental Hospital against their oppressive nurse. It’s a highly enjoyable adaptation of Ken Kesey’s novel which allows Jack Nicholson full creative freedom, unleashing the natural boyish charm which made him so successful at his career inception.

1. The Shining (Stanley Kubrick – 1980)

Covering several genres across the director’s illustrious career, Stanley Kubrick’s turn at the horror genre, adapting Stephen King’s The Shining leads to one of the genres greatest films, and Jack Nicholson’s most quintessential performance.

Set in the magnificent, fictional Overlook Hotel, the tale follows Jack Torrance (Jack Nicholson) and his family who opt to look after the hotel over the winter, where a violent evil begins to influence his quickly crumbling mental state.

Nicholson’s cruel psychotic descent is a true marvel to watch, elevating the performances of his co-stars, particularly Shelley Duvall who radiates an unrivalled physical fear. The Shining is a mesmerising horror experience crafted by Kubrick but piloted by Nicholson.