Although he had appeared as a member of The Tarriers in "Calypso Heat Wave" (1957), Arkin made his feature acting debut as a stranded Soviet submariner afloat in the USA in Norman Jewison's Cold War spoof "The Russians Are Coming, The Russians Are Coming" (1966), earning a Best Actor Oscar nomination. He demonstrated his dramatic range as the psychopathic killer opposite Audrey Hepburn in "Wait Until Dark" (1967), then reinvented himself again as the sensitive, deaf-mute protagonist of "The Heart Is a Lonely Hunter" (1968), for which he received a second Academy Award nomination as Best Actor. Arkin took on yet another ethnic identity for his hysterical starring turn in Arthur Hiller's "Popi" (1969), playing a Puerto Rican father struggling against big odds to make a better life for his family. He followed with perhaps his highest profile part, that of Captain Yossarian in Mike Nichols' film version of Joseph Heller's antiwar novel "Catch-22" (1970). Although it has acquired a following, the movie did not initially live up to expectations, and as a result, Arkin's career suffered.

Arkin made an impressive Sigmund Freud opposite Nicol Williamson's Sherlock Holmes in "The Seven-Per-Cent Solution" (1977) and roared all the way back to the top with Peter Falk in Hiller's "The In-Laws" (1979), scripted by Andrew Bergman and executive-produced by Arkin. Unpredictably wacky from start to finish, it cast him as a dentist who becomes involved in the bizarre intrigues of his daughter's father-in-law (Falk) and provided him comic flourishes similar to those with which he had made his name on both stage and screen. In the early 80s he acted in three movies that were family affairs, "Chu Chu and the Philly Flash" (1981, written by wife Barbara Dana with a part for son Adam as well), "Improper Channels" (1981, written by Adam) and Larry Cohen's teenage werewolf comedy "Full Moon High" (1982, starring Adam with a cameo for Tony). He also turned in a terrific performance as James Woods' colorful dad in "Joshua Then and Now" (1985) and was particularly memorable leading an escape from a death camp in the riveting CBS movie "Escape from Sobibor" (1987).

Arkin, who has enjoyed success as a stage, film and TV director, made his Off-Broadway debut with "Eh?" (1966), introducing Dustin Hoffman, then segued into film, helming the shorts "Thank God It's Friday" (1967), and "People Soup" (1969), which he also produced. He earned a Drama Desk Award for his direction of the Off-Broadway revival of Jules Feiffer's "Little Murders" (1969), and the following year's "The White House Murder Case" brought him both a Drama Desk Award and an OBIE. He then made his feature debut directing the film version of "Little Murders" (1971) before scoring a resounding success in his Broadway directorial debut, Neil Simon's "The Sunshine Boys" (1972). Arkin tackled TV next, sharing the helm with Clark Jones on "Twigs" (CBS, 1975), adapted by George Furth from his Broadway play. Though he has helmed only one additional feature to date, the poorly received "Fire Sale" (1977), his efforts for TV have included "The Visit" (1987) and "The Boss" (1989) for PBS' original comedy series "Trying Times.”

Arkin started out the 90s with a bang acting in three features, including Tim Burton's dark satire "Edward Scissorhands" (1990), before contributing to the ensemble tour de force "Glengarry Glen Ross" (1992). He starred as a bitter former baseball player in TNT's "Cooperstown" (1993) and delivered a vivid supporting turn as Nick Nolte's neighbor in "Mother Night (1996). In 1997, he appeared in two very different projects, "Grosse Pointe Blank", which featured him in some hilarious scenes as hitman John Cusack's psychiatrist, and the sci-fi "Gattaca,” playing a detective tracking a killer. The Oscar-nominated foreign-film "Four Days in September" (1997) cast him as the American ambassador to Brazil, kidnapped by rebels in 1969, and he followed that with "The Slums of Beverly Hills" (1998) opposite Marisa Tomei. Arkin also returned to the New York stage as co-author and co-star of "Power Plays" (1998), working with son Tony, Elaine May and May's daughter Jeannie Berlin. He subsequently portrayed a judge in the ensemble drama "100 Centre Street" (A&E, 2001-02), which marked Sidney Lumet's return to the small screen.

Arkin returned to the big screen with “Thirteen Conversations About One Thing” (2002), an ensemble drama that emerged from the 2002 Sundance Film Festival about a group of people living in New York City who live separate lives completely unaware of the subtle interconnections that bring them together. Arkin played a pessimistic insurance company manager troubled by his ex-wife and delinquent son who enjoys deflating his more cheery employees. In “The Pentagon Papers” (FX Network, 2003), a made-for-cable-TV movie about former Defense Department employee Daniel Ellsberg and his struggle to leak top secret military secrets about the Vietnam War to the New York Times, Arkin played Ellsberg’s Rand Corporation boss, a role that earned the actor an Emmy Award nomination for Outstanding Supporting Actor in a Miniseries or a Movie. That same year, Arkin was seen in another cable movie, “And Starring Pancho Villa as Himself” (HBO, 2003), a true-life telling of the famed Mexican revolutionary (Antonio Banderas) and his outrageous offer to allow Hollywood to make a movie of his exploits while using the money he made to fund his war efforts.