- 2009: Played Amy Adams and Emily Blunt's father in the independent film, "Sunshine Cleaning"
- 2008: Played The Chief in the adaptation of Mel Brooks and Buck Henry's hit 1960s spy parody show, "Get Smart"
- 2008: Played Owen Wilson's boss in the family film, "Marley and Me"
- 2007: Co-starred with Meryl Streep and Reese Witherspoon in "Rendition"
- 2007: Played an elderly handyman in director Neal Miller's character-driven comedy drama, "Raising Flagg"
- 2006: Played a foul-mouthed grandfather with a taste for heroin in the indie comedy, "Little Miss Sunshine"; earned a SAG nomination for Best Supporting Actor
- 2003: Cast in the FX mini-series "The Pentagon Papers"; received a Best Supporting Actor Emmy nomination
- 2001: Headlined the ensemble cast of the A&E series "100 Centre Street"
- 1998: Returned to the stage in the Off-Broadway play (also co-authored) "Power Plays"; also starred son Anthony, Elaine May and May's daughter Jeannie Berlin
- 1998: Played the family patriarch in "The Slums of Beverly Hills"
- 1997: Played American ambassador to Brazil in the Oscar-nominated foreign film "Four Days in September"
- 1997: Offered a hysterically funny turn as hitman John Cusack's psychiatrist in "Grosse Point Blank"
- 1996: Played George Kraft in film version of Kurt Vonnegut's "Night Mother"
- 1995: Appeared in "Jerky Boys: The Movie"
- 1993: Played a bitter ex-ballplayer in TNT's "Cooperstown"
- 1992: Joined a heavyweight cast for the film version of David Mamet's "Glengarry Glen Ross"
- 1990: Offered a satiric turn as suburbanite in "Edward Scissorhands"
- 1988: Co-wrote (with wife Barbara Dana from her novel) and co-starred with her in the PBS special "Necessary Parties"
- 1987: Co-executive producer and star of short-lived ABC series "Harry"; also starred wife Barbara Dana
- 1987: Directed, "The Visit," the fifth episode of PBS' first original comedy series, "Trying Times"
- 1987: Delivered an Emmy-nominated turn in CBS movie "Escape from Sobibor"
- 1985: Won critical praise as James Woods' colorful dad in "Joshua Then and Now"
- 1982: Provided the voice of Schmendrick the Magician in the animated feature "The Last Unicorn"
- 1981: Teamed with Carol Burnett in the film "Chu Chu and the Philly Flash"; scripted by Arkin's then wife Barbara Dana
- 1979: Feature producing (executive producer) debut, "The In-Laws"; also acted; second film with director Hiller
- 1977: Portrayed Sigmund Freud to Nicol Williamson's Sherlock Holmes in "The Seven-Per-Cent Solution"
- 1977: Last feature directed to date, "Fire Sale"; also acted
- 1975: Co-directed (with Clark Jones) George Furth's TV adaptation of his play "Twigs" (CBS)
- 1975: Directed episodes of NBC's short-lived series "Fay" starring Lee Grant
- 1972: Broadway directorial debut, Neil Simon's "The Sunshine Boys"
- 1971: Feature film directing debut, "Little Murders"; also acted
- 1970: Landed plum role in Mike Nichols' film adaptation of Joseph Heller's antiwar novel "Catch-22"; initial tepid response hurt his career; film has since acquired cult status
- 1969: Directed Off-Broadway revival of Jules Feiffer's "Little Murders"
- 1969: Starred in Arthur Hiller's "Popi"; earned a Best Actor Golden Globe nomination
- 1968: Earned second Best Actor Oscar nomination as a deaf mute loner in "The Heart is a Lonely Hunter"
- 1967: Terrorized a helpless and blind Audrey Hepburn in "Wait Until Dark"
- 1967: Made short film directing debut, "T.G.I.F"
- 1966: Off-Broadway directing debut, "Eh?"; credited as Robert Short
- 1966: Feature acting debut, "The Russians Are Coming, the Russians Are Coming"; earned Best Actor Oscar nomination
- 1963: Screen acting debut in short, "That's Me"
- 1963: Delivered Tony-winning turn in Carl Reiner's "Enter Laughing"
- 1961: Broadway debut in the revue, "From the Second City"
- 1960: Became a member of Chicago's Second City Group
- 1959: Joined the improvisational group The Compass Players at the Crystal Palace in St. Louis, Missouri
- 1958: Off-Broadway debut, "Heloise"
- 1958: Recorded four albums of songs for children with group, The Babysitters
- Recorded albums and was a founding member of the folk group The Tarriers



