'Chasing Amy' - 1997
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In Kevin Smith's classic '90s romantic comedy "Chasing Amy", Affleck plays a comic book artist who falls for a woman, played by Joey Lauren Adams, who happens to be a lesbian.
Things get (more) complicated when they actually begin a relationship, leading to heartbreak and broken friendships.
'Good Will Hunting' - 1997
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After a string of roles in Hollywood movies throughout the '90s, Affleck and longtime friend Matt Damon crafted their own success, co-writing and starring in the acclaimed drama "Good Will Hunting", which won them a Best Original Screenplay Oscar, and earned Robin Williams the Best Supporting Actor prize.
'Armageddon' - 1998
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Affleck became a blockbuster star, thanks to his role as one member of a team of deep-core oil drillers who travel to space to destroy an asteroid threatening all life on Earth in Michael Bay's "Armageddon".
'Gone Girl' - 2014
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Affleck had some dark fun with his own public image, starring as a man accused of killing his wife in David Fincher's acclaimed thriller "Gone Girl", based on the bestselling novel by Gillian Flynn.
'Gone Baby Gone' - 2007
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After reaching a low point in his career, Affleck crafted a comeback by getting behind the camera to co-write and direct the crime-drama "Gone Baby Gone".
The acclaimed film starred his brother Casey Affleck and was based on the novel by Dennis Lehane.
'The Town' - 2010
Photo: THE CANADIAN PRESS/HO, TIFF, Warner Bros. - Claire Folger
Affleck followed up his directorial debut, "Gone Baby Gone", with 2010's "The Town", in which he also joined his ensemble cast in front of the camera.
Based on the novel Prince of Thieves, by Chuck Hogan, the crime-thriller follows a team of bank robbers in Boston who attempt to rob Fenway Park in one last score.
'To The Wonder' - 2012
Affleck got the opportunity of a lifetime, working with acclaimed director Terrence Malick in the 2012 film "To the Wonder".
The beguiling film tells the story of a couple who fall in love in Paris, only to find their relationship breaking apart when they move to the U.S.
'Argo' - 2012
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Though he failed to secure a Best Director nomination, Affleck won the Oscar for Best Picture with his 2012 true-life drama "Argo", about the mission to extract Americans hiding in the Canadian embassy in Tehran during the Iran Hostage Crisis.
'The Way Back' - 2020
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After years of struggling with addiction, Affleck plumbed his own history for the emotional sports drama "The Way Back".
The actor played an alcoholic construction worker who becomes the head coach of his old high school's basketball team where he was once a star player.
'The Last Duel' - 2021
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More than two decades after "Good Will Hunting", Affleck re-teamed with Matt Damon, as well as Nicole Holofcener, to co-write the historical drama "The Last Duel", directed by Ridley Scott.
The film, which flopped at the box office but earned praise from critics, tells the story of a woman in medieval times who is raped by a friend of her husband, and must watch as her fate is decided in trial by combat.