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Milestones
- 2003: Co-starred in the mini-series "The Pentagon Papers"; received an Emmy nomination for Outstanding Supporting Actor In A Miniseries Or A Movie
- 2001: Co-starred in "13 Conversations About One Thing"; screened at Toronto; shown at the 2002 Sundance Film Festival
- 1998: Acted opposite Marisa Tomei in "The Slums of Beverly Hills"
- 1998: Returned to off-Broadway stage as co-author and co-star of "Power Plays", working with son Anthony, Elaine May and May's daughter Jeannie Berlin
- 1997: Cast as Charles Elbrick, the American ambassador to Brazil kidnapped by Brazilian radicals in 1969, in the Oscar-nominated foreign film "Four Days in September", directed by Bruno Baretto
- 1997: Offered a hysterically funny turn as hitman John Cusack's psychiatrist in "Grosse Point Blank"
- 1997: Portrayed Detective Hugo in sci-fi feature "Gattaca"
- 1996: Played George Kraft in film version of Kurt Vonnegut's "Night Mother", starring Nick Nolte
- 1995: Appeared in "The Jerky Boys" movie (in a moment of poverty)
- 1993: Starred as bitter ex-ballplayer in "Cooperstown", a TNT movie written by playwright Lee Blessing and directed by Charles Haid
- 1992: Joined a heavyweight cast in film version of David Mamet's "Glengarry Glen Ross", playing a complaining, endangered, vetern real estate salesman
- 1990: Offered a satiric turn as suburbanite in "Edward Scissorhands"
- 1988: Co-wrote (with wife Barbara Dana from her novel) and starred with her in award-winning PBS special "Necessary Parties"
- 1987: Directed "The Visit" (written by Christopher Durang), the fifth episode of PBS' first original comedy series, "Trying Times"
- 1987: Delivered an Emmy-nominated turn in CBS movie "Escape from Sobibor"
- 1987: Co-executive producer and star of short-lived ABC series "Harry"; also starred wife Barbara Dana
- 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 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: Directed episodes of NBC's short-lived series "Fay", starring Lee Grant
- 1975: Co-directed (with Clark Jones) George Furth's TV adaptation of his play "Twigs" (CBS), starring Carol Burnett
- 1972: Broadway directorial debut, Neil Simon's "The Sunshine Boys"
- 1971: Feature film directing debut, "Little Murders"; also acted
- 1970: Landed plum role of Yossarian in Mike Nichols' film adaptation of Joseph Heller's antiwar novel "Catch-22", but initial tepid response hurt his career; film has since acquired cult status
- 1969: Starred in Arthur Hiller's "Popi", a charming story of poverty in the ghetto, focusing on Arkin's character's zany antics in securing a better life for his children
- 1969: Directed Off-Broadway revival of Jules Feiffer's "Little Murders"
- 1968: Earned second Best Actor Oscar nomination as deaf mute loner in "The Heart is a Lonely Hunter", based on Carson McCullers' first novel
- 1967: Short film directing debut, "T.G.I.F"
- 1967: Terrorized a helpless and blind Audrey Hepburn in "Wait Until Dark"
- 1966: Off-Broadway directing debut, "Eh?"; credited as Robert Short
- 1966: Feature film acting debut in "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; co-starred in improvisational revue, "Second City"
- 1959: Joined the improvisational group The Compass Players at the Crystal Palace, St Louis, Missouri
- From 1958 to 1968: Recorded four albums of songs for children with group, The Babysitters
- 1958: Off-Broadway debut as Singer in "Heloise"
- Headlined the ensemble cast of the A&E series "100 Centre Street"
- Founded, recorded albums and performed with folk singing group, The Tarriers
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