Hannah And Her Sisters
"Hannah And Her Sisters" (1986)
Back before Woody Allen’s Grand European Tour, when he still made films in New York, “Hannah and Her Sisters” was one of his finest, telling the story of three tightly knit sisters and their extended family in Manhattan. Caine and Allen might not seem like an obvious combination, but his storming turn as Elliot, husband to Mia Farrow's Hannah, won him his first Oscar. A bespectacled middle-aged accountant, Elliot pursues his wife’s vivacious younger sister Lee (Barbara Hershey). As the affair commences, Elliot is not only a philanderer, but also caddishly blames his wife’s self-sufficiency and emotional strength for his wandering eye. Playing another character we should hate, Michael Caine makes us believe in Elliot and the earnestness of his torn feelings between Hannah and her sister. Elliot lacks the panache of Alfie and the dignity of Caine’s later roles, but we are forced to feel for Elliot as he searches for what he thinks is the answer (“For all my education, accomplishments and so-called wisdom, I can't fathom my own heart”) rather than viewing him merely as a middle-aged lech (“She looks so sexy in that sweater. I just want to be alone with her and hold her and kiss her…”). Almost thirty years later, Elliot still resonates with audiences, as Peter Bradshaw wrote in his Guardian review, “Caine's performance, so fervent, so agonisingly dedicated, actually gains in force and touching sincerity with the years.”

Dirty Rotten Scoundrels
“Dirty Rotten Scoundrels” (1988)
An unofficial remake of "Bedtime Story" starring David Niven and Marlon Brando, "Dirty Rotten Scoundrels" follows two very different conmen on the French Riviera as they are wined and dined by rich female tourists. Unlike others on this list, "Dirty Rotten Scoundrels" is strictly a comedy (and one that makes you wonder why he doesn't go broad more often), but like in the other films, Caine plays a real cad. Lawrence Jamieson (Caine) is a suave and sophisticated con artist who seduces gullible but not wholly innocent women and relieves them of their wealth. Lawrence’s modus operandi involves convincing these women of a certain age that he is an exiled prince who needs funds to rally his troops and reclaim his birthright. In Caine’s portrayal, Lawrence is catnip for these bored, too-rich-for-their-own-good women with his dashing looks and classic charisma – stealing their hearts and their wallets. Lawrence’s financial future is threatened by the appearance of Freddy Benson (Steve Martin), a small-time crook who has taken an interest in the very same women Lawrence is after – “A poacher who shoots at rabbits may scare big game away.” Whether battling over an American soap queen or teaming up to get rid of a mark, Caine and Martin are a laugh riot. In the end, it turns out that Lawrence’s heart is as golden as his bank account, and we have fallen in love with Michael Caine all over again, even as a thief, liar, and con man. Martin might get the most uproariously funny scenes (particularly in his moments as Prince Ruprecht), but Caine's the perfect, ultra-suave foil for him, and gets almost as many laughs.

Quiet American
"The Quiet American" (2002)
The second adaptation of the Graham Greene novel, the film is set in 1952 Vietnam, and sees Caine play Thomas Fowler competing with an American CIA agent (Brendan Fraser) for the love of local beauty Phuong (Hai Yen). As Fowler, Caine plays an eyewitness to the development of the Vietnam War and used Greene as inspiration in developing his character, telling the BBC that, "I didn’t know him very well, but I knew a great deal about him. […] I knew a lot by proxy. I just copied something of the way he [Greene] spoke, and his movements. They were very small." He did it so successfully that the film garnered some success and a few nominations in spite of having been shelved for a year in the wake of 9/11 and cries over supposed anti-American sentiments. But Caine trudged on and succeeded where many others would fail. His role here is among his most complex and textured performances, and deserves a look by anyone that might have skipped it first time around.

Caine Children Of Men
"Children Of Men" (2006)
After seeming to settle into the position of highly respected older British supporting actor (see "Cider House Rules" and "Batman Begins"), Michael Caine shook things up by playing an aged hippy in "Children of Men." Taking second seat to the main plot of Theo's (Clive Owen) attempt to save humanity through a miraculously pregnant woman, the star plays Jasper, a former political cartoonist who spends his days smoking weed and listening to tunes in the woods. Even as the world is crumbling around him, Jasper says, “Pull my finger!” Although a minor part, the actor steals a few scenes (“Your baby is the miracle the whole world has been waiting for”), providing real levity in an otherwise tough film (playing air guitar to Aphex Twin), and pathos in his heroic last stand. In "Children of Men," Caine’s versatility is tested and he comes out on top yet again.

Michael Caine, TDKR
"The Dark Knight Rises" (2012)
In his twilight years, Caine has become the unexpected muse of one of the biggest filmmakers in the world: he's featured in the last five of Christopher Nolan's films (and has apparently been promised a role in his next, "Interstellar") proving a reliable, sly supporting hand from "Batman Begins" to "Inception." They're all fine performances (even one as brief as in "Inception") but perhaps Caine's finest Nolan hour so far came in last year's "The Dark Knight Rises." Of all the relationships Bruce Wayne has had throughout Nolan’s trilogy, none have been as important as that with Alfred, his most important father figure. As the man who raised him, and promised his parents to look out for the young man for the rest of his life, Alfred has grappled with Bruce’s desire to save Gotham even as it so very often comes at the risk of his own life. And in “The Dark Knight Rises,” Alfred reaches the limit of what he can stand by and watch Bruce do. With his body battered, spirit waning and public image still tarnished, Bruce is very much on the path of martyrdom early in the movie (and seemingly pretty much suicidal), something the world-wise Alfred recognizes all too well, and he will have no part of it. When he announces to Bruce that he can no longer in good conscience be with him -- and reveals at the same time the contents of Rachel’s letter from “The Dark Knight” as a last resort to get Master Wayne to move on from his plans to return as Batman -- it’s a crushing scene. And Caine is absolutely shattering in it, delivering one of the best pieces of acting in the entire trilogy, and giving the film a much-needed emotional core, the trilogy a lovely arc for Bruce and Alfred.

Honorable Mentions: Possibly the biggest omission here is "The Cider House Rules," the film that won Caine his second Oscar. It's as fine a turn, but perhaps one of those Oscar wins that's for a breadth of career achievement rather than the specific performance itself. That said, it did allow Caine to give one of the all-time greatest Oscar speeches, which you can watch below.

Other performances we considered, but didn't quite have time for include "Gambit," "The Italian Job," "The Eagle Has Landed," "California Suite," "Educating Rita," "Last Orders," "Is Anybody There?" and "Harry Brown." Any others you feel deserve a mention? Let us know below.  

- Diana Drumm, Oliver Lyttelton