Alan Arkin, an acclaimed actor who excelled at both comedy and drama over the course of his more than 70-year-career, died Thursday at age 89.

From his Tony Award–winning career breakthrough in the early 1960s to his first Academy Award win in the 2000s, Arkin’s career was defined as much by its longevity as it was the actor’s casual wit and exceptional talent. Below are 10 of the greatest performances from the late actor’s long and diverse career.

Enter Laughing (1963)

After starting his career in the early 1960s with the Second City improv comedy troupe and some television appearances, Arkin had his breakout performance in the Broadway play Enter Laughing in 1963. A farcical comedy based on actor Carl Reiner’s autobiography, Arkin earned a Tony Award for his performance as David Kolowitz, an aspiring young actor in the Bronx. “The show ran for a year and made him a star,” according to The New York Times.

The Russians Are Coming, the Russians Are Coming (1966)

alan arkin wearing a navy hat and uniform in a submarine
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Alan Arkin portrayed a Soviet Union Navy lieutenant in The Russians Are Coming, the Russians Are Coming.

Arkin earned his first Oscar nomination for playing a Soviet Union Navy lieutenant in a submarine that becomes grounded in a New England town in this Cold War satire. Arkin, who grew up in a Russian Jewish household, spoke English and Russian fluently in the role, according to the Encyclopedia of Jewish American Popular Culture. Variety called Arkin “absolutely outstanding as the courtly Russian who kisses a lady’s hand even as he draws a gun.”

Watch The Russians Are Coming, the Russians Are Coming

The Heart Is a Lonely Hunter (1968)

alan arkin and sondra locke in the film the heart is a lonely hunter
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Alan Arkin and Sondra Locke in the film The Heart is a Lonely Hunter

Arkin received a second Academy Award nomination for his performance as John Singer, a deaf-mute in a small southern town during the Depression, in this adaptation of the classic 1940 novel by Carson McCullers. “Walking, with his hat jammed flat on his head, among the obese, the mad, the infirm, characters with one leg, broken hip, scarred mouth, failing life, he somehow manages to convey every dimension of his character, especially intelligence,” The New York Times wrote.

Watch The Heart Is a Lonely Hunter

Catch-22 (1970)

alan arkin and three other actors wearing military uniforms in a publicity photo from the film catch 22
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Alan Arkin (right) in a scene from Catch-22

Arkin played the lead role in this anti-war satire, based on the novel of the same name by Joseph Heller. In portraying Captain John Yossarian, a U.S. Army Air Force bombardier whose determination to survive World War II leads to several comedic exploits, Arkin said: “It was the only part I’ve ever worked on which didn’t demand a conception, because there isn’t much difference between me and Yossarian.”

Watch Catch-22

The Sunshine Boys (1973)

Arkin stepped off of the stage and into the director’s seat in 1973, when he directed a Broadway production of this Neil Simon play about an estranged vaudeville comedy duo who reunite for a TV special. Simon chose Arkin to direct the play after a falling out with the playwright’s usual directing partner, Mike Nichols, who had demanded a larger percentage of the show’s profits, according to Acting Foolish, an autobiography by actor Lewis J. Stadlen.


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Escape from Sobibor (1987)

One of Arkin’s most celebrated television performances was his portrayal of Leon Felhendler, a Polish resistance fighter, in this British TV film based upon a real-life mass escape of Jewish prisoners from the Nazi extermination camp at Sobibor in 1943. Arkin earned an Emmy nomination for his performance as Felhendler, who helped organize the prisoner uprising, according to Indelible Shadows: Film and the Holocaust by Annette Insdorf.

Watch Escape from Sobibor

Thirteen Conversations About One Thing (2001)

Arkin appeared in several supporting film roles throughout the 1990s, including The Rocketeer, Glengarry Glen Ross, and Gattaca. But he earned some of his best reviews in years for his performance in Thirteen Conversations About One Thing, a 2001 film featuring a large ensemble cast and a story told in 13 vignettes. Arkin was nominated for an Independent Spirit Award and National Society of Film Critic Award and won the Boston Society of Film Critics award for Best Supporting Actor.

Watch Thirteen Conversations About One Thing

Little Miss Sunshine (2006)

alan arkin wearing a black suit and holding an oscar
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Alan Arkin won an Academy Award for Best Supporting Actor in 2006.

More than five decades into his acting career, Arkin finally won his first Academy Award for Little Miss Sunshine, in which he played the caustic grandfather in a dysfunctional family driving across the country to a child beauty pageant. “More than anything, I am deeply moved by the open heart and appreciation our small film has received, which in these fragmented times, speaks so openly of the possibility of innocence, growth, and connection,” Arkin said during his Oscar acceptance speech.

Watch Little Miss Sunshine

Argo (2012)

ben affleck and alan arkin wearing suits and smiling to each other
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Ben Affleck and Alan Arkin attend a screening of Argo in September 2012.

Arkin received another Oscar nomination six years later—again for a comedic supporting performance—for his role in this Ben Affleck–directed film inspired by the real-life C.I.A. mission to rescue six U.S. diplomats from Tehran during the 1979 Iran hostage crisis. Arkin portrayed Lester Siegel, a film director who cooperates with Affleck’s CIA agent character, and who bitingly delivers one of the film’s most memorable lines: “Argo f–– yourself!”

Watch Argo

The Kominsky Method (2018-19)

michael douglas and alan arkin, wearing gray suits and black shirts, sitting on chairs on a stage
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Michael Douglas and Alan Arkin speak onstage about The Kominsky Method in June 2019 in Los Angeles.

Arkin continued acting into the final years of his life, and one of his most memorable late-career performances was Norman Newlander in The Kominsky Method, a Netflix comedy-drama series. Newlander is the agent and friend of the show’s protagonist, a washed up actor and Hollywood acting coach played by Michael Douglas. The performance earned Arkin Emmy nominations in two consecutive years.

Watch The Kominsky Method

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Colin McEvoy
Senior News Editor, Biography.com

Colin McEvoy joined the Biography.com staff in 2023, and before that had spent 16 years as a journalist, writer, and communications professional. He is the author of two true crime books: Love Me or Else and Fatal Jealousy. He is also an avid film buff, reader, and lover of great stories.