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Affleck has described this period of his life as "dreamlike": "It was like one of those scenes in an old movie when a newspaper comes spinning out of the black on to the screen. Good Will Hunting had not yet been released during the casting process and, after Affleck's screen test, director Michael Bay dismissed him as "a geek".He was convinced by producer Jerry Bruckheimer that Affleck would be a star, Later in 1998, Affleck had a supporting role as an arrogant English actor in the period romantic comedy Shakespeare in Love, starring his then-girlfriend Gwyneth Paltrow.Affleck's first starring film role was as an aimless art student in the college drama Glory Daze (1995), with Stephen Holden of The New York Times remarking that his "affably mopey performance finds just the right balance between obnoxious and sad sack".He then played a bully in filmmaker Kevin Smith's comedy Mallrats (1995), and became friends with Smith during the filming.Affleck worked "sporadically" on Mimi from the age of eight to fifteen in both Massachusetts and Mexico.

Affleck's most notable role during this period was as a high school bully in Richard Linklater's cult classic Dazed and Confused (1993).Stephen Holden of The New York Times wondered why actors like Affleck and Peter O'Toole had agreed to appear in the "junky" film: "Affleck's thudding performance suggests he is reading his dialogue for the first time, directly from cue cards." Affleck and Damon had an on-screen reunion in Kevin Smith's religious satire Dogma (after having appeared in Smith's previous films, Mallrats and Chasing Amy), which premiered at the 1999 Cannes Film Festival.Janet Maslin of The New York Times remarked that the pair, playing fallen angels, "bring great, understandable enthusiasm to Mr. Affleck starred opposite Sandra Bullock in the romantic comedy Forces of Nature (1999), playing a groom whose attempts to get to his wedding are complicated by his free-spirited traveling companion.He starred in the psychological thriller Gone Girl in 2014.In 2016, Affleck began playing Batman in the DC Extended Universe, starred in the action thriller The Accountant, and directed, wrote and acted in the gangster drama Live by Night.