Jack Nicholson’s 12 best movies – from Easy Rider to The Departed

Nicholson already had 19 film credits to his name by the time he appeared in Dennis Hopper's counter-cultural classic Easy Rider, but it was with his memorable supporting turn as alcoholic lawyer George Hanson that he truly broke out as a major star – earning an Oscar nomination for Best Supporting Actor and emerging as a key face in the New Hollywood movement.

The film sees two hippies (played by Hopper and Peter Fonda) take a cross-country trip on their Harley-Davidsons, travelling from Southern California to New Orleans while undergoing something of a journey of self-discovery. The film is now considered as a key cultural touchstone, and Nicholson's scenes are easily some of the most memorable – especially a scene in which he is introduced to marijuana. It also contains one of the best soundtracks of all time – with hits from The Band, The Byrds and The Jimi Hendrix Experience among those to feature.

Another landmark from the New Hollywood era, Bob Rafelson's drama Five Easy Pieces sees Nicholson take on the lead role of Robert Dupea, a dissatisfied oil rig worker who reluctantly takes a trip home to visit his middle-class family – all of whom are professional musicians – after learning that his father is gravely ill.

Undoubtedly one of the best, most nuanced performances of Nicholson's career (it earned him another Oscar nod), the film is a fascinating, if not exactly cheerful, study of alienation, which especially hit a chord with American audiences in the early '70s. It also includes one of the best food-ordering scenes in cinema.

Nicholson is exceptional as one of two Navy officers tasked with escorting a convict to prison in this excellent Hal Ashby drama from a script by Robert Towne (more on him later). His character Billy "Badass" Buddusky is initially far from enthusiastic about the task but he and his companion Richard "Mule" Mulhall soon take something of a shine to their charge – leading to some unexpected bonding.

Another film that very much spoke to the time and place in which it was made, the film carries a fairly pessimistic message but includes several extremely enjoyable scenes along the way – as the trio attend parties, drink in hotel rooms, and encounter a group of Nichiren Buddhists. Ashby, who also made such films as Harold and Maude and Coming Home, provides typically assured direction, with Nicholson delivering some of the best line readings of his career.

After the success of The Last Detail, Nicholson again paired with Robert Towne for his next project, with Roman Polanski this time the man behind the camera. Towne's Oscar-winning screenplay has long been hailed as one of the best in Hollywood history, and the film serves as more or less the essential neo-noir – complete with all the sharp dialogue and cynism you'd want.

Set against the backdrop of a major water dispute, the plot concerns the investigation undertaken by private eye JJ "Jake" Gittes (Nicholson) into the husband of a rich socialite, who soon winds up dead. Gittes – fedora, nose bandage and all – is unquestionably one of Nicholson's most iconic characters, and the film also features one of the most memorable closing lines of all time. "Forget it Jake, it's Chinatown."

This adaptation of Ken Kesey's classic novel swept the Oscars in 1976 – a year where the other Best Picture nominees included such classics as Jaws, Nashville, Barry Lyndon, and Dog Day Afternoon, no less. It won the five biggest awards, including Nicholson's first Best Actor gong, and remains one of only three films to ever achieve that feat.

Nicholson stars as Randle McMurphy, a new patient at a mental institution who causes chaos when he rails against the tyrannical reign of the coldly cruel Nurse Ratched (Louise Fletcher) – becoming something of a rebellion leader for his fellow inmates. It's a film fully deserving of its stellar reputation and another of Nicholson's finest turns.

Stephen King famously didn't approve of Stanley Kubrick's haunting adaptation of his 1977 novel – and indeed the film had something of a mixed reception upon its initial release. But it has endured to become one of the most iconic horror movies of all time, and with good reason: as a nightmarish, surrealist descent into one man's madness, it's rarely, if ever, been bettered.

Containing all the visual splendour you'd expect from such a master filmmaker, the film conjures up all manner of mesmerising images that have become staples in horror iconography and continues to generate much discussion and theorising. And of course, Nicholson is truly unforgettable as Jack Torrance – especially as the character veers further and further into insanity. Heeeeere's Johnny!

Nicholson has played a number of villains and anti-heroes in his career – but in George Miller's charming comedy The Witches of Eastwick he goes one step further by playing the literal embodiment of the devil himself. His character is Daryl Van Horne, a charismatic and rather beguiling man who suddenly pitches up at the titular New England town shortly after three of its single female residents have wished for a new man to enter their lives.

Initially won over by his plentiful charms, things then start to go somewhat awry for the three women (played brilliantly by Cher, Michelle Pfeiffer, and Susan Sarandon) as they begin to question if he's really as good as he first seemed. Nicholson is clearly having an absolute blast in the role – offering one of the most scenery-chewing, flamboyant performances of a career that's been dominated by them, and proving that he's just as adept at comedy as he is in more serious roles.

Ever since the late Heath Ledger's outstanding performance in The Dark Knight, portrayals of the Joker have tended to focus on the more dark and gritty aspect of the supervillain's personality. But it wasn't always this way – and in Tim Burton's majestic 1989 Batman adaptation, Nicholson turns in a spectacularly goofy performance as the Caped Crusader's arch-nemesis, offset brilliantly by the more straight-laced turn by Michael Keaton in the title role.

A far cry from the more serious adaptations of this source material that were to follow from the likes of Christopher Nolan and more recently Matt Reeves, Burton's gothic film is a wonderfully eccentric and cartoonish interpretation of the comics and is furiously entertaining from beginning to end, as Batman desperately tries to stop Nicholson's Joker from causing chaos in Gotham.

Although he appears second on the cast billing, behind only star Tom Cruise, Nicholson is actually absent for the vast majority of Rob Reiner's thoroughly enjoyable adaptation of Aaron Sorkin's play. But the scenes in which he does appear are extremely memorable – virtually the dictionary definition of scene-stealing – and deservedly earned him another Oscar nomination for Best Supporting Actor.

Nicholson plays Colonel Nathan R Jessup, a hard-nosed marine officer who proves very uncooperative in helping navy lawyer Daniel Kaffee's (Cruise) investigation into the death of a marine who died on his watch. The courtroom scenes at the film's climax are especially well-played and feature yet another iconic Nicholson line: "You can't handle the truth" – which is delivered in a rather more low-key way than you might expect.

Unless he makes a spectacular return from retirement, Alexander Payne's comedy-drama from 2002 will go down as Jack Nicholson's last Oscar-nominated performance. In the film, which is loosely based on the 1996 novel of the same title by Louis Begley, Nicholson takes on the role of Warren Schmidt, a recently bereaved, newly retired insurance company actuary who has rather lost his way in life.

Essentially a quirky road trip movie – a genre which Payne has since returned to with both Sideways and Nebraska – About Schmidt is packed with heart and humour, and Nicholson is simply perfect as the lead. Schmidt is undoubtedly a far less outlandish character than many of the oddballs and outcasts he's become famous for portraying, but it's no less impressive a performance from the great actor – and thoroughly deserving of the praise it received.

Nicholson and Diane Keaton are in fine form in this typically delightful rom-com from Nancy Meyers, starring as two polar opposite singles who unexpectedly find themselves falling for each other after a less than ideal meet-cute. The pair – who had previously starred together in the epic period film Reds – bounce off each other spectacularly, and it's impossible not to become invested in their unlikely romance.

The film doesn't exactly reinvent the wheel, but it's a heart-warming, smart, and most importantly funny film that also happens to be one of the few prominent examples of the rom-com genre to focus on characters over the age of 50. There are also several enjoyable supporting performances from a cast that includes Keanu Reeves, Frances McDormand and Amanda Peet.