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The 15 Movies You Need to Watch to Understand Michael Caine’s Career

With his seventh Christopher Nolan collaboration hitting theaters (maybe?) soon, let’s look back at the beloved British movie icon’s career highlights (well, mostly)

When Tenet makes its belated debut in (some) North American theaters this week it will undoubtedly feature a bunch of director Christopher Nolan’s signature touches, from striking visuals to a twisty narrative that requires viewers pay attention or risk getting lost. It will also feature an actor who’s become something of a Nolan trademark: Michael Caine, making his seventh appearance in one of Nolan’s films (eight if you count his vocal cameo in Dunkirk). It’s the longest sustained collaboration Caine has enjoyed with any filmmaker, a fact made all the more remarkable by the now-87-year-old Caine’s extensive filmography — he’s appeared in over 130 films and shows no signs of slowing down — and that he first appeared in one of Nolan’s films just 15 years ago, when he took on the part of Alfred Pennyworth in Batman Begins.

As anyone who’s seen Steve Coogan and Rob Brydon’s dueling impressions in The Trip can attest, Caine’s voice and manner of delivery has gone through different eras. But so has Caine’s career and the sort of roles he’s taken on. The sage counselor parts he’s played for Nolan belong to the most recent era, but hardly represent the full scope of Caine’s career. Nor do the 15 films listed below in rough chronological order, which can only capture a fraction of his work, but each represents a different aspect of Caine’s film work, and combined are a good starting point for those wishing to delve deeper into all things Caine, while collectively doubling as a history of Caine on film. They’re also all pretty terrific films in their own right. (Well, most of them anyway, but that’s also part of the Caine story.)

Alfie (1966)

Caine’s story doesn’t begin with Alfie, but his career wouldn’t have taken the shape it did without the role that made him synonymous with Swinging London. On paper, he seemed an unlikely icon for 1960s youth: Born Michael White to working-class London parents in 1933, he’d already served in the military, gotten married, fathered a child and gotten divorced before the Beatles released Please Please Me. He’d also already enjoyed a respectable acting career on stage, in films and on television before the 1964 hit Zulu — which gave him a plum role as an officer that required him to adopt a posh accent, rather than his natural Cockney speaking voice — made him a proper star. Then Alfie, in which Caine plays a charming but heartless London womanizer, made him a superstar. 

He took the part only after his roommate Terence Stamp — to whom he’d served as a mentor when Stamp was starting out — passed, having tired of the role after playing it on stage. That choice made Caine an icon of the decade’s carefree attitudes and liberated sexuality, even though the film takes a more jaded view of Alfie’s lifestyle: His monologues about how great he has it and how little he cares grow less convincing as the consequences of his actions pile up. That didn’t stop the character from influencing Caine’s public image, however, or burnishing his reputation as one of London’s great playboys.

The Ipcress File (1965)

“You’re supposed to be a great ladies’ man,” Dick Cavett once asked Caine before continuing, “and yet you wear glasses.” Cavett was only half-joking. Caine never fit the profile of a big-screen sex symbol and often found roles that leaned into this fact. In The Ipcress File, Caine plays Harry Palmer, a Ministry of Defense employee charged with investigating the disappearance of some scientists. Though the film shares a producer, composer and production designer with the James Bond series, Palmer is in most respects Bond’s antithesis, a rumpled man living in a grubby flat who spends much of the film several steps behind the bad guy. But even in such deglamorized conditions, Caine still radiates charisma. (Palmer’s pretty lucky with women, too.) Caine would play Palmer twice more in the 1960s, then revisit the character in the 1990s.

The Italian Job (1969)

As the 1960s drew to a close, Caine still found himself landing parts as playboy charmers of questionable character, this time out in a caper film that starts as a clever, lighthearted romp, then builds to a finale filled with driving stunts that have to be seen to be believed. Caine plays a just-out-of-prison crook who comes into the possession of a plan for the heist to end all heists — so long as he can assemble a team capable of essentially shutting down the city of Turin, evading the Mafia, then making a daring escape through the Alps. Working from a script by Troy Kennedy Martin, director Peter Collinson fills the film with cheeky humor and colorful characters, all revolving around the orbit of Caine’s Charlie Croker, a man who never loses his unflagging confidence up to and including a daring final scene that’s best left unspoiled. 

Thanks in part to some oddly somber advertising, the film never picked up more than a cult following in the U.S., but it became a hit in Britain and elsewhere, helping cement Caine’s stardom and making an icon of the Mini Coopers that essentially serve as Caine’s co-stars.

Get Carter (1971)

Helping darken Caine’s image for the decade to come, Mike HodgesGet Carter finds him playing a different sort of criminal in the form of Jack Carter, a London gangster who returns home to Newcastle after the death of his brother via an “accident” Jack feels the need to investigate. Once there he discovers an even grubbier underworld than the one he knows as he sets about taking violent vengeance on those who’ve wronged his family and, he later discovers, victimized his niece. Unsparingly grim and disturbingly violent, the film met with a mixed reception in the U.K. and flopped in the U.S. — though it inspired the blaxploitation sort-of remake Hit Man — but saw its reputation soar when audiences rediscovered it in the 1990s and directors like Guy Ritchie used it as a touchstone for their own British underworld films. (Caine also turns up in a 2000 remake starring Sylvester Stallone, but the less said about that the better.)

Sleuth (1972)

Based on a seemingly unadaptable play by Anthony Shaffer, Sleuth pairs Caine with Laurence Olivier as characters whose testy (to say the least) relationship doubles as a clash between two different ages of British screen acting. Olivier plays Andrew Wyke, a mystery writer living in an old house filled with strange knick-knacks. (Any similarity between this setting and that of Rian Johnson’s Knives Out is certainly not coincidental.) Caine plays Milo Tindle, the man Wyke knows to be his wife’s lover and the intended victim of a murder Wyke believes to be unsolvable. The twisty, claustrophobic film lets Caine play another cad, but it also allows him to step beyond that sort of role in ways, again, best left unspoiled. (And, in a bit of a pattern, Caine would appear in its little-liked 21st century remake, this time in the part of Wyke.)

The Man Who Would Be King (1975)

John Huston tried to make this adaptation of a Rudyard Kipling story for over 20 years, initially planning to shoot it with Clark Gable and Humphrey Bogart. As good as that might have been, it’s hard to imagine a better pairing than Caine and Sean Connery, who play former British soldiers-turned-con men determined to bilk the far-off land of Kafiristan of its treasure, only to push their luck too far. Huston brings a light touch to a tale of high adventure with both Connery and Caine matching his tone. But the film also uses their hubris to cast a jaundiced eye at imperialism, as Connery’s character starts to buy into his own scheme and Caine’s begins to recognize that their arrogance will prove their undoing.

Dressed to Kill (1980)

A capital “P” problematic classic, Brian De Palma’s riff on Psycho can most charitably be seen as a time capsule for some of the era’s truly ill-informed ideas about sexual identity. (Or, if you’re being really charitable, a parody of the same.) But, if you can get past that (and that might be too big an “if” for some), it’s a fascinating, brutally well-executed thriller. Caine’s performance as a therapist with an unusually intense interest in one of his patients also speaks to where he was at this point in his career: He’d aged out of parts written for dashing rogues but discovered new possibilities instead. A few years earlier, he slipped into the ensemble of the Neil Simon adaptation California Suite, playing a gay man at a time when actors of his stature rarely dared. Never one in the habit of saying “no,” he showed up for easy paychecks in Irwin Allen thrillers like The Swarm and took weird chances like starring as a cartoonist menaced by his own severed hand in The Hand. Why not? He was Michael Caine, and the movies still wanted him, even if they wanted him for different sorts of roles than the ones that made him famous.

Educating Rita (1983)

Unafraid to play men in the grips of midlife crises, Caine reunited with Alfie director Lewis Gilbert for another stage adaptation in 1983, this time out a Willy Russell play. Caine stars as Frank Bryant, a poet-turned-alcoholic literature professor who’s charmed by the latest non-traditional student to turn up at his office as part of Britain’s Open University: a fast-talking hairdresser nicknamed Rita (Julie Walters). Sensing real, raw passion for literature that’s still untouched by the education system’s conventional wisdom, he takes her on as a project, then finds himself developing feelings for her as their time together progresses. The film made a star of Walters and Caine’s wistful performance helped reshape his image for the 1980s nearly as much as Alfie did in the 1960s, setting him up for some of the middle-aged romantic roles that followed.

Hannah and Her Sisters (1986)

Chief among these roles: Elliot, the husband to Mia Farrow’s Hannah, who burns with desire for Hannah’s sister Lee (Barbara Hershey) in one of the interweaving stories that make up Woody Allen’s bittersweet portrait of two years in the life of an extended New York family. One of film’s great shouters — as that Coogan/Brydon face-off emphasizes — Caine can be just as effective working in a lower register. Here he remains staid and smiling on screen while his voiceover expresses a yearning he can no longer contain. The performance earned him the first of his two Best Supporting Actor Oscars.

Jaws: The Revenge (1987)

Not that he was around to collect it. Caine was unable to attend the ceremony due to reshoots for Jaws: The Revenge, the truly terrible third sequel to Jaws in which he plays a semi-shady Bahaman pilot named “Hoagie.” There’s a certain pleasure to watching Caine give his all in films he has to recognize are beneath him, and his filmography is filled with them, from The Swarm to the Steven Seagal-directed On Deadly Ground (in which he plays an unlikely Texan). But Caine never winks even when pitted against a shark with a grudge, as he is here. Of the film, he famously said, “Somebody said, ‘Have you ever seen Jaws 4?’ I said, ‘No. But I’ve seen the house it bought for my mum. It’s fantastic!’” 

Mona Lisa (1986)

Sometimes an actor can take over a movie even with limited screen time (providing he’s not competing with a shark). In Neil Jordan’s Mona Lisa, Caine plays Denny Mortwell, a London sex trafficker with an eye on the bottom line and little regard for the human lives being destroyed to shore up his profits. He’s both a criminal and the embodiment of uncaring capitalism, and Caine plays him with a casual callousness so chilling that his threatening shadow hangs over the film even when he’s nowhere to be seen.

Dirty Rotten Scoundrels (1988)

Caine has enjoyed tremendous success bringing breezy charm to a variety of films, but has a spottier record when it comes to straight-up comedies, which he started to appear in with greater frequency in the 1980s. One sterling exception: Frank Oz’s delightful tale of con artists working the French Riviera. Caine plays a refined, British seducer content to fleece unsuspecting women. Steve Martin co-stars as his crude American rival-turned-protege who joins him in a partnership that involves increasingly elaborate schemes and ridiculous disguises. They’re so delightful together (and playing opposite co-star Glenne Headly) it’s a shame they never teamed up again, or that Caine only rarely got comedic material this strong, or partners so equally matched.

The Muppet Christmas Carol (1992)

On the other hand, sometimes it’s best just to play it straight when surrounded by chaos. Part of what makes Caine’s turn as Ebeneezer Scrooge so affecting is that it would work even if teleported into a more straightforward Dickens adaptation. He finds the emotions of the character and lets them guide the performance, rather than acknowledging that he’s surrounded by felt creatures. The approach makes the lighter moments seem that much sillier, the moving moments that much more touching, and turns the film into one the most memorable versions of an oft-told story

The Cider House Rules (1999)

Caine won his second Best Supporting Actor trophy playing an orphan director/secret abortionist in this adaptation of John Irving’s novel set in Maine in the years leading up to and including World War II. The film marked something of a turning point in his career, the moment when roles in which he played older men reflecting on the lives they’d led and considering their legacies started to outnumber other types of characters. His willingness to adapt would serve him well in the years that followed.

Inception (2010)

Nolan first worked with Caine on Batman Begins and has stuck with him ever since for a couple of obvious reasons: 1) If an actor of Caine’s caliber wants to keep working with you, you don’t mess that up; and 2) if you make heady films filled with difficult concepts, it helps to have a calm, authoritative center to keep them grounded. Caine’s played variations on that part throughout his Nolan collaborations, and in Inception his cool, professorial insistence not only helps untangle some of Nolan’s more cerebral ideas, it gives them a tangible emotional weight. Caine’s work with Nolan might just be part of a busy schedule, one that also includes Dear Dictator and this year’s Four Kids and It — dubious-looking projects he undoubtedly approaches with the same level of professionalism he’s always employed. 

In his 1987 special Michael Caine: On Acting in Film, Arts and Entertainment, part of a BBC series on acting, Caine fills an hour with practical advice about hitting marks and holding the camera. (Key tip: Don’t blink.) But for Caine it’s not a matter of putting craft over art, it’s recognizing that art arises from craftsmanship. It’s his job, and he’s just kept working, in films both good and bad, sophisticated and crude, always trying his best to elevate both with his contributions without seeming to devote a thought to retirement. Caine seems to think that there will always be a place for him no matter how much time passes and fashions change. 

So far, nothing has proved him wrong.

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