best film: With Michael Caine’s long career (archiveable films span fifty-six (56) years – from 1964 to 2020), vast collection of archiveable films (twenty-nine (29)), and his collaborations with Christopher Nolan – this category requires some maneuvering. Starting with Nolan might be easiest. Caine is unfortunately not physically in Nolan’s strongest work, the 2017 film Dunkirk – so Inception is the top contender here from their frequent collaborations. The Ipcress File is stunning and has to be broached. Non-auteur masterpieces are few and far between – so kudos to Caine for having this film on his resume. Brian De Palma’s Dressed to Kill (1980) is worthy of a mention as well – so there is depth in this category for Caine. Ultimately though, Alfonso Cuaron’s 2006 film Children of Men is the winner – and an easy top one-hundred (100) of all-time film – more than one can say for the others.

from Alfonso Cuaron’s Children of Men (2006) – The Rolling Stones song “Ruby Tuesday” is used twice for five seconds each to great affect – once to show emotion on Clive Owen’s beaten face remembering his son – and the other with Michael Caine’s goodbye to his wife. Caine dazzles in his few scenes – humor, life, vitality in a bleak world.
best performance: Michael Caine, on the surface, may seem like an odd casting choice for a Woody Allen film – but Hannah and Her Sisters is Caine’s best performance. Most of the males in Woody’s films are either Woody himself or Woody surrogates – everyone from John Cusack (Bullets Over Broadway) to Kenneth Brannagh (Celebrity) to Owen Wilson (Midnight in Paris) to Jesse Eisenberg (Café Society). Rarely, Allen would pick someone that strays from that type (his type) and go with a more imposing figure or masculine lead like Caine (Gene Hackman in Another Woman is another example of this). Caine is Get Carter and Alfie after all – bastions of virility. Regardless, the results are sublime here. Caine somehow makes this pretty sickening character sympathetic – or if not sympathetic then at least real, human, and pitiable.

Hannah and Her Sisters (1986) – Woody’s film is perfect and definitely a candidate to be his best film post Manhattan in 1979. This is an ensemble film with more than enough meat on the bone for all three sisters (Diane Wiest, Mia Farrow and Barbara Hershey) along with Allen himself who acts in the film and, of course, Michael Caine who walks away with the best performance in the film. It is a tribute to Caine that his character does not come off as more repulsive (“despicable” as he says in the film) than he does . He is charmingly awkward in his fawning over Hershey’s character and his own self hatred helps to soften the blow on the audience.
stylistic innovations/traits: Michael Caine has six (6) Oscar nominations, two (2) wins (both for supporting – Hannah and Her Sisters in 1986 and the win over Tom Cruise in 1999 for The Cider House Rules), and has twenty-nine (29) archiveable films. Caine likes to work – very prolific. He has roughly 150 film credits and is not overly picky in role choices (hurt him a few times – in notorious bombs like The Swarm and Jaws: The Revenge). But still, Caine, taking his name from Humphrey Bogart and The Caine Mutiny (1954), has had a very long and prestigious career. Zulu is 1964 and 21st century cinephiles are certainly very familiar with Caine from the Nolan films and there are no overwhelming gaps between. Caine, unlike say an Anthony Hopkins or Christopher Plummer (two notorious sort of late peakers) was a big time star in the 1960s. His take on Anthony Perkins (but in doctor form) is fascinating in Dressed to Kill and assuredly his work with Nolan in the 21st century should not be underestimated. His story about the Joker and watching the world burn in The Dark Knight so important to the film. Caine is a little hurt on this list because Hannah and Her Sisters as his single best role – is a weakness – at least for an actor in the top fifty (50) on this list. Caine’s case rests upon that overwhelming body of work with seven (7) straight decades (Tenet now in the 2020s) with an archiveable film, and five (5) straight with an Oscar nomination (ranging from the 1960s to 2000s).

from The Ipcress File (1965) – this is the first of three in a trio of adaptations from Len Deighton’s books. Caine would star again as Harry Palmer in Funeral in Berlin (1966) and Billion Dollar Brain (1967- and neither directed by Sidney Furie). Palmer is akin to James Bond – and it is worth noting that Caine and Sean Connery would come together in 1975’s The Man Who Would Be King as a sort of Cold War spy agents Batman vs. Superman. With all due respect to 007 – no one Bond film hits the cinematic high-water mark The Ipcress File does. Caine was famous for his spectacles in the 1960s. He is in Gambit in 1966. Apparently Shirley MacLaine (at the height of her star power clout in 1966) hand picked Caine and brought him over across the pond for his first Hollywood film.
directors worked with: Christopher Nolan (7), Joseph L. Mankiewicz (1), John Huston (1), Brian De Palma (1), Sidney Lumet (1), Woody Allen (1), Alfonso Cuaron (1), Paolo Sorrentino (1)

Dressed to Kill (1980) – it is somewhat complex set up. Michael Caine plays Doctor Robert Elliott – a psychiatrist. He is treating Angie Dickinson’s Kate Miller. There is a murder (Psycho-like stabbing) and Brian De Palma (ever the Alfred Hitchcock acolyte) will part with the recognizable female lead early in the film) where Liz Blake (Nancy Allen) is a witness. The victim’s son (Keith Gordon as Peter Miller) works with Allen’s character to help solve the crime. Caine is not only a very worthy actor for certain, but is also perfectly cast in the psychiatrist role.
top five performances:
- Hannah and Her Sisters
- The Ipcress File
- The Man Who Would be King
- Dressed to Kill
- Get Carter
archiveable films
1964- Zulu |
1965- The Ipcress File |
1966- Alfie |
1966- Funeral in Berlin |
1966- Gambit |
1967- Billion Dollar Brain |
1971- Get Carter |
1972- Sleuth |
1975- The Man Who Would Be King |
1975- The Wilby Conspiracy |
1977- A Bridge Too Far |
1978- California Suite |
1980- Dressed to Kill |
1982- Death Trap |
1986- Hannah and Her Sisters |
1986- Mona Lisa |
1988- Dirty Rotten Scoundrels |
1999- The Cider House Rules |
2000- Quills |
2002- The Quiet American |
2005- Batman Begins |
2006- Children of Men |
2006- The Prestige |
2008- The Dark Knight |
2010- Inception |
2012- The Dark Knight Rises |
2014- Interstellar |
2015- Youth |
2020- Tenet |
Do you think his work in Children of Men or The Dark Knight is stronger?
@Matthew- Tough one, what do you think? Can I take option C and say “The Dark Knight Rises?”
I maybe prefer the Children of Men role (and film) more overall but ultimately I would (atleast for now) go with TDK just because the “some men just want to watch the world burn” monologue always gives me chills. I even prefer his performance there to the one on in Rises slightly just because of that scene, although I get it, the scene with him and Bale on the stairwell “It also means losing someone I have cared for since I first heard his cries echo through this house.“ is phenomenal stuff
On a semi-related note, if you combined all of the Alfred Pennyworth performances (so the entirety of TDK trilogy) into one performance how high do you think that would rank for Caine?
@Matthew – I think it would slide into that 5th slot
The case against calling Plummer and Hopkins late bloomers is Plummer is a big part of 1965’s Sound of Music and Hopkins plays a crucial part in the 1968 Oscar winner Lion in Winter. Both films with high artistic merits.
@Malith -Well aware, still… they are late bloomers. That case would be wrong
Drake, love the site. Small correction: Caine is in Dunkirk, but it’s just a vocal cameo. He plays Tom Hardy’s squadron leader over the radio
@Haider- Thanks- changed the language here
Can Michael Caine play working class men in Kitchen sink realism movies say saturday night and sunday morning?
I think he can’t. He’s masculine but he does not have a rugged masculinity that early Albert Finney had.
@M*A*S*H- I am not recasting Finney here, but with his masculinity and cockney accent- I’d watch the version with Caine and have high hopes for the performance
What according to you is the best Kitchen Sink realism movie. To me it’s The Entertainer from the master of the movement Tony Richardson. Saturday Night and Sunday Morning is extremely close. And 2 of Jack Clayton’s films.
I find this movement very rarely talked about and I just love the movies from this period of british cinema.
@M*A*S*H- I love the movies from this period in British cinema as well. Kes is listed here https://en.wikipedia.org/wiki/Kitchen_sink_realism – we’re getting into genre and subgenre definitions – but certainly you list some of the best here.
“Caine is a little hurt on this list because Hannah and Her Sisters as his single best role – is a weakness – at least for an actor in the top fifty (50) on this list.”
Is this more to do with the quality of the film or the fact he isn’t the lead?
@Harry – perhaps a little a both – just a small differentiator