- 2008: Reprised role of Alfred in the second installment of the revived "Batman" series, "The Dark Knight"
- 2008: Co-starred with Demi Moore in "Flawless"
- 2007: Played the role of Andrew Wyke (originally portrayed by Laurence Olivier) in the adaptation of the 1972 film "Sleuth"; caine also starred in the original opposite Olivier (played by Jude Law in the remake)
- 2006: Again collaborated with director Christopher Nolan for "The Prestige"
- 2006: Played a pot-smoking hippie in Alfonso Cuaron's futuristic tale "The Children of Men"
- 2005: Played Nicole Kidman's ancient warlock father in the comedy "Bewitched"
- 2005: Cast as Bruce Wayne's butler Alfred in Christopher Nolan's "Batman Begins"
- 2003: Portrayed Pierre Brossard, a Nazi executioner in the film "The Statement"
- 2002: Played a British journalist in Phillip Noyce's "The Quiet American"; received Golden Globe, BAFTA and Oscar nominations
- 2002: Appeared in "Austin Powers in Goldmember"
- 2001: Starred in the dramatic film "Last Orders" which premiered at the Toronto Film Festival
- 2000: Co-starred with Jeffrey Rush and Kate Winslet in the critically acclaimed "Quills"
- 1999: Won second Academy Award as Dr. Larch in Lasse Hallström's "The Cider House Rules"; adapted by John Irving
- 1998: Received rave reviews for his turn as a sleazy talent agent in "Little Voice"
- 1995: Reprised the role of Harry Palmer in the Showtime original "Bullet to Beijing"
- 1994: Portrayed Joseph Stalin in the NBC miniseries "World War II: When Lions Roared"
- 1993: Co-produced (also starred) the HBO spy drama, "Blue Ice"
- 1988: Co-starred with Steve Martin as con artists in the Frank Oz directed comedy, "Dirty Rotten Scoundrels"
- 1988: American TV miniseries debut, "Jack the Ripper" (CBS)
- 1987: Debut as executive producer, "The Fourth Protocol"
- 1986: Won first Oscar as Mia Farrow's cheating husband in Woody Allen's "Hannah and Her Sisters"
- 1983: Received third Best Actor Oscar nomination as an alcoholic university professor who mentors a promising female student in "Educating Rita"
- 1980: Had starring role in Brian De Palma's stylized thriller "Dressed to Kill"
- 1975: Co-starred opposite Sean Connery in John Huston's epic adventure "The Man Who Would Be King"
- 1972: Received second Best Actor Oscar nomination for his work opposite Laurence Olivier in "Sleuth"
- 1969: Starred in the British cult favorite "The Italian Job"
- 1966: First American film, "Gambit" opposite Shirley MacLaine
- 1966: Earned first Best Actor Oscar nomination for the woman-chasing title character in "Alfie"
- 1965: Debuted working-class spy Harry Palmer in "The Ipcress File"
- 1964: First starring feature role, playing against type as posh Lieutenant Gonville Bromhead in "Zulu"
- 1960: Appeared at the Royal Court Theatre in London
- 1956: Film acting debut in a bit part in "Hell in Korea"
- 1954: Appeared in Theatre Workshop in Stratford East, London and Sam Wanamaker's company in Liverpool
- 1951: Drafted for the National Service and spent one year in West Berlin and another in the Royal Fusiliers in combat in Korea
- 1949: Worked on set of the British film, "Morning Departure"
- Began acting apprenticeship while still in grammar school
- First theater job, assistant stage manager at Westminster Repertory Theatre; led to work with Lowestoft Repertory Theater
- Attended night drama classes, supporting himself with various day jobs
- Began appearing regularly on TV in mid-1950s
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