It's truly amazing how much longevity Michael Caine's acting career has had. He first became a star in the mid-1960s and has worked steadily in the decades since, establishing himself as a household name to multiple generations. He has the rare distinction of being nominated for Oscars in five different decades, and though it was reported in 2021 that he was considering retirement, Caine has since walked back that claim, meaning viewers may not have seen the last of him on screen.

With well over 100 feature film credits to Caine's name, it's daunting to try and single out the best of the best, and any ranking that doesn't include every film of his will ultimately miss some notable ones. What lies below are the names of some of his very best films, taking into consideration both how great the movie itself is and how it showcases Caine's talents as an actor. They also demonstrate how he excels in every genre he tackles, as well as signifying how he's earned the right to be called one of cinema's greatest actors.

25 'The Last Valley' (1971)

Director: James Clavell

The Last Valley is a far from perfect movie, but it is supremely underrated. It lost a sizable amount of money at the box office, and to this day still isn't particularly well-known, with its story set during the Thirty Years' War in the 1600s seemingly doomed to never find an audience.

Though The Last Valley's story isn't perfectly told, and Caine's accent in the movie is - to put it mildly - ambitious. The Last Valley is gorgeously shot, and it has an unbelievably great score by John Barry. Michael Caine also commits fully to the role, and his co-star, Omar Sharif, is similarly compelling, making for a sometimes uneven but ultimately rewarding watch that's been slept on by many for more than half a century now.

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24 'The Ipcress File' (1965)

Director: Sidney J. Furie

Though The Ipcress File was rebooted as a TV miniseries in 2022, the original movie from 1965 shouldn't be overlooked. It was one of Michael Caine's earliest starring roles, and in it, he plays a spy who gets wrapped up in a complex plot involving scientists, kidnapping, and brainwashing.

The Ipcress File is one of those deeply paranoid mystery/thriller films that can be hard to follow, but it feels that way by design, given how Caine's character is almost constantly out of his depths. It does a great job of making viewers feel similarly challenged and confused, all the while keeping its pacing tight and its complicated narrative intriguing.

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23 'Dirty Rotten Scoundrels' (1988)

Director: Frank Oz

In Dirty Rotten Scoundrels, Michael Caine co-stars with Steve Martin, and two play... well, scoundrels who are both dirty and rotten. More specifically, they're both con men, and they engage in a competition with each other, with both trying to scam a wealthy heiress out of $50,000 before the other can.

As far as crime movies go, Dirty Rotten Scoundrels definitely one of the more light-hearted ones out there. Still, it's quite fun to watch, with Caine and Martin making for a great pairing, and it's primarily their charisma/chemistry that keeps the movie feeling entertaining throughout.

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22 'Zulu' (1964)

Director: Cy Endfield

If there's one role that can be pointed to as the one that began Michael Caine's rise in popularity, it's his performance as Lt. Gonville Bromhead in Zulu. This war movie from the 60s is based on the real-life Battle of Rorke's Drift, which took place in 1879 and saw 150 British soldiers defending a field hospital from a thousands-strong army of Zulu warriors.

Within the large cast, it's Caine who stands out the most, with his performance here making it easy to understand why he became one of the best-known British actors in the years that followed. The film is quite spectacular when it comes to depicting the battle, and is overall technically impressive, even if some modern-day viewers may feel troubled about watching a film like this where British colonial forces are the central focus.

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21 'Austin Powers in Goldmember' (2002)

Director: Jay Roach

Fundamentally changing the way audiences viewed the series it spoofed, spy movies haven't been the same since the Austin Powers trilogy, with three films released between 1997 and 2002. While few people would say Goldmember is the best of the three, it does feature Michael Caine in a prominent role, which has to count for something.

Caine's featured here as the father of the title character, and is perhaps the best addition to the cast, showcasing how (shockingly) good he is at comedy, despite his drama roles tending to be more well-known. And without being too hard on Goldmember, it is still a fun comedy, though it's for the best that it was the final Austin Powers movie, given the Caine-less parts of the series were beginning to wear a little thin.

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20 'The Wrong Box' (1966)

Director: Bryan Forbes

A silly and underrated crime comedy movie, The Wrong Box isn't very well-known, but deserves to be counted among Michael Caine's best early roles. It's a darkly comedic and farcical movie that follows various family members trying to get their hands on a fortune that's set to be inherited by one of two elderly brothers - whoever outlives the other.

Everything gets more ridiculous and convoluted as it goes along, with various outlandish scenarios stacking up on top of each and building, all the way to a gleefully wild climax. Caine's fantastic in an early comedic role, and the rest of the cast is impressive, too, considering the film also features the likes of Peter Sellers and Dudley Moore.

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19 'Deathtrap' (1982)

Director: Sidney Lumet

It's becoming apparent already that Michael Caine excels in crime comedies, especially ones with plenty of outlandish plot twists (1966's flawed but entertaining Gambit contains one of the best). Deathtrap isn't quite his best crime comedy role, but it's up there, with this comedic mystery/thriller doing all it can to ensure viewers won't be able to guess where it goes next.

Caine plays a playwright who'll go to great lengths to steal a play written by a young and talented student (played by Christopher Reeve). It doesn't exactly hide the fact it was based on a stage play, but this does naturally lend the film a compelling meta element, given it's centered on playwrights. The film's overall very entertaining and quite funny, and worth watching for those who love films that are overflowing with plot twists.

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18 'The Cider House Rules' (1999)

Director: Lasse Hallström

Michael Caine won his second Oscar for The Cider House Rules, where he plays the supporting role of a doctor who mentors an orphan named Homer, who's in turn trained to be a doctor. It spans a good deal of time, with the movie beginning in the 1920s and ending after World War 2, primarily serving as a coming-of-age story for Homer (Tobey Maguire).

The Cider House Rules has got a fairly slow pace and feels undeniably sentimental at times, but for the kind of movie it's trying to be, it's undeniably effective. Michael Caine's performance might not leap out as being one of his very best, but he's still good overall (he's rarely not), making his second Academy Award well-earned.

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17 'Mona Lisa' (1986)

Director: Neil Jordan

Mona Lisa (the 1986 film, not the painting) does ultimately belong to Bob Hoskins, whose lead performance earned him an Oscar nomination. Michael Caine still excels in a supporting role, though, in this film about a recently released prisoner who takes on the role of driving a high-class call girl from customer to customer.

It's a neo-noir through and through, having more outwardly adult content than the film noir movies of old while retaining the style and moral ambiguity that tends to define the genre. It's also easy to see it as a precursor to The Crying Game (1992), with both films sharing a director (Neil Jordan) and, by extension, a similar style and overall feel.

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16 'A Bridge Too Far' (1977)

Director: Richard Attenborough

It's astounding just how many big-name actors are in A Bridge Too Far, with Michael Caine ultimately being one of many in its ensemble cast. He's joined in this World War 2 film by James Caan, Sean Connery, Elliott Gould, Gene Hackman, Anthony Hopkins, Laurence Olivier, Robert Redford, and Liv Ullmann, to name just a few.

There were big names behind the camera, too, with Richard Attenborough as its director and William Goldman as its screenwriter. The large-scale film depicts 1944's Operation Market Garden, which aimed to make an Allied invasion into northern Germany easier to accomplish. A Bridge Too Far is old-fashioned and very long, but its spectacle and impressively huge cast ensure its runtime goes by reasonably fast.

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15 'Dressed to Kill' (1980)

Director: Brian De Palma

One of many compelling thriller movies directed by Brian De Palma, Dressed to Kill co-stars Nany Allen as a sex worker who witnesses a grisly murder, only to find herself the next potential target of a serial killer. Things get progressively messier, and the film's plot gets continually twistier with each passing scene.

Dressed to Kill is the kind of outlandish thriller you kind of have to give yourself over to, but in large part, it really works, and Michael Caine is great as always. Some of the content hasn't aged as well as the film's style and frenetic pacing, but those who don't mind their thrillers going to some wild places should find a good deal to be entertained by here.

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14 'The Prestige' (2006)

Director: Christopher Nolan

You can't talk about Michael Caine's career without bringing up the films of Christopher Nolan, as the frequent collaborations between the two have helped keep Caine a popular and recognizable actor well into the 21st century. Caine has appeared in seven of Nolan's films between 2005 and 2020, with 2006's The Prestige being one of them.

It's a mystery-heavy thriller about two magicians in the late 1800s who develop a fierce rivalry, with each pushing themselves to their limits to outdo and outwit the other. Like many films by Nolan, it aims to keep viewers on their toes and wrapped up in a complex plot, with The Prestige satisfying as a story while featuring great performances from Caine, Hugh Jackman, Christian Bale, and Scarlett Johansson, among others.

13 'Get Carter' (1971)

Director: Mike Hodges

Get Carter was a defining film for the neo-noir genre, to which the aforementioned Mona Lisa (1986) also belongs. Its central premise involves revenge, with Michael Caine playing a gangster who believes someone's responsible for his brother's death in an alleged car accident, and will stop at nothing to find out who.

Of course, once he finds out who was behind it, then his mission turns to one of vengeance, which is where things get particularly dark. It's an uncompromising film for its time, and showed how Caine could excel in more hard-edged roles, given that at its core, Get Carter is a bleak, gritty, and violent crime movie.

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12 'Alfie' (1966)

Director: Lewis Gilbert

The title character of Alfie was arguably born in the wrong decade, as he's a womanizer who would've loved online dating apps that have had people swiping throughout the past 10 or so years. Caine slips into this role with ease, successfully showing Alfie to be someone who's charismatic while also deeply flawed, with the movie following the way he discovers how his actions have consequences.

It's quite provocative for its time, and also would've felt novel for the way it presents its narrative, given Alfie frequently breaks the fourth wall and addresses the audience. It serves as a comedy that morphs into more of a drama as it goes along, making for a sometimes challenging but ultimately rewarding watch that, in some ways, still surprisingly holds up.

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11 'Inception' (2010)

Director: Christopher Nolan

After two Christopher Nolan-directed Batman movies that set the box office on fire, it's no wonder why Inception was so highly anticipated. To this day, it's still one of Nolan's very best movies, having a unique heist movie premise that follows a team who infiltrates the dreams of their target and attempts to implant an idea within his subconscious mind.

These play out as a series of exciting and imaginative action sequences, though Michael Caine's role is relegated to the film's quieter (and more exposition-heavy scenes), as he's a professor who's also the protagonist's mentor. Still, Caine shines in Inception, showing once again how well he can slip into the ensemble cast of a Nolan-directed film.

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10 'Kingsman: The Secret Service' (2014)

Director: Matthew Vaughn

Even though it hasn't exactly taken off as a franchise, the first Kingsman movie, The Secret Service, was a surprise hit and still holds up as an entertaining action/comedy movie. It follows a spy organization training a young man to become a secret agent who clashes with a wealthy tech genius who has an odd yet dangerous plan to take over the world.

It can be pretty crude and juvenile, but it's undeniably funny in parts and has a good deal of great action. Thanks to starring in his fair share of spy thrillers and comedies over the decades, Michael Caine slips right into his role as the leader of Kingsman, expertly handling the surprisingly complex role he has to play in the film.

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9 'The Muppet Christmas Carol' (1992)

Director: Brian Henson

Few actors appearing in live-action would dedicate themselves so thoroughly to a Muppet movie, but Michael Caine went a step or two beyond the norm with his role as Ebenezer Scrooge in The Muppet Christmas Carol. The core story is of course familiar, but the presentation is novel, with more comedy (and far more puppets) than you'd expect from the standard A Christmas Carol adaptation.

Caine was quoted as saying: "I am going to play Scrooge as if it is an utterly dramatic role and there are no puppets around me." His resulting performance undeniably succeeds at this, with him bringing a surprising level of depth to the role, and helping to ensure The Muppet Christmas Carol endures as an iconic holiday movie.

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8 'Interstellar' (2014)

Director: Christopher Nolan

Interstellar is something of a modern classic within the sci-fi genre, and arguably Christopher Nolan's most ambitious film to date. It's set in a future where Earth is slowly becoming inhabitable, forcing a group of astronauts to venture out into space, in search of a new planet for humanity to live on.

Interstellar also provides Michael Caine with maybe his most complex role in a Nolan movie, with him playing a NASA scientist in charge of the operation who's also a mentor to the main character and the father of another significant character. He makes the most of all his scenes in another great supporting role, and to date, it's his penultimate credited role in a Nolan film, seeing as he only made a brief appearance in Tenet and isn't slated to appear in Oppenheimer.

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7 'The Italian Job' (1969)

Director: Peter Collinson

While younger viewers might be more familiar with the 2003 version of The Italian Job, that one's not as great as the original from 1969. The first Italian Job is an iconic heist movie about a gang of thieves who plan to use a traffic jam to steal a large quantity of gold, only to find that their perfect plan doesn't exactly unfold perfectly.

That's the way most good heist movies go, after all. It's kind of boring when everything seems to work out as planned. Michael Caine plays the leader of the team, Charlie Croker, and gets to be equal parts cool and silly in this exciting yet comedic crime movie. The Italian Job stands to this day as perhaps the best movie from the 1960s to star Caine.

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6 'Youth' (2015)

Director: Paolo Sorrentino

Youth is ironically not about young people. It's a dramedy that stars Michael Caine and Harvey Keitel as two friends who are getting on in life, and look back on what they've done in their years while vacationing in the Swiss Alps, leading to plenty of impressive scenery that's captured in typically dazzling style, thanks to Paolo Sorrentino's directorial flair.

Youth shows one of the greatest performances of the last 10 to 20 years from Caine (and Keitel, too, who's equally excellent). It's naturally bittersweet, with its story fluctuating between funny and dramatic, but it balances tones well overall, and makes for a compelling and somewhat underrated film that's well worth checking out.

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