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:

  1. Hannah and Her Sisters
  2. The Ipcress File
  3. The Man Who Would be King
  4. Dressed to Kill
  5. 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