‘Chasing Amy’ To ‘Argo': Ben Affleck’s Five Defining Films

By Colin Greten

Ben Affleck has been in the Hollywood spotlight for a long time now, but as a star, he has taken on many different forms. He has gone from an Oscar-winning screenwriter, to a leading man, to a disreputable actor and the butt of jokes, to acclaimed director. With his latest film “Argo” now receiving praise—many claiming it’s the best of the year—it’s safe to wonder how Affleck made this transformation.

We’ve been able to break it down to five movies, so here are the films that have defined the journey of Ben Affleck.

“Chasing Amy” (1997)
“Chasing Amy” was “Clerks” director Kevin Smith’s third feature film and one of the first starring roles for the young Affleck. He already made an appearance in Smith’s “Mallrats,” but “Chasing Amy” gave him the chance to prove he could carry a film with some dramatic themes, as he falls in love with the perfect girl (Joey Lauren Adams), who turns out to also be a lesbian. Although the film is low-budget, it was decently successful and showed that Smith and Affleck both had staying power in Hollywood. Affleck continued to act in Smith movies throughout his career, including a hilarious cameo as himself in “Jay and Silent Bob Strike Back” (2001).

“You gotta do the safe picture, then you do the art picture… and sometimes you gotta do the payback picture because your friend says you owe him.” –Ben Affleck in Smith’s “Jay and Silent Bob Strike Back.”

“Good Will Hunting” (1997)
Along with childhood friend Matt Damon, Ben Affleck wrote the script for “Hunting,” winning the Oscar for Best Original Screenplay. It has always been rumored that Damon was more of the brains behind the project, although that has never been proven and is perhaps a result of resentment towards Affleck early in his career. “Good Will Hunting” meant that both Affleck and Damon had officially arrived on the Hollywood scene and that their careers would be linked together forever.

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“Gigli” (2003)
Despite starring in the successful “Armageddon” (1998) and having a supporting role in Best Picture Winner, “Shakespeare in Love” (1998), Affleck’s acting career took a serious downturn. “Reindeer Games” (2000), “Pearl Harbor” (2001), “Daredevil” (2003), “Paycheck” (2003) and “Jersey Girl” (2004) were all extreme disappointments both critically and at the box office. However, no film epitomizes Affleck’s dry spell more than “Gigli” (2003) which starred then fiancé Jennifer Lopez and is considered one of the biggest flops of all time, grossing a mere six million at the box office, despite a high budget. Affleck’s series of busts as an actor made him laughable to most viewers as he seemingly took roles for the money rather than ones that really suited him.

“Gone Baby Gone” (2007)
After the series of poor showings previously mentioned, Affleck began taking less roles focusing on quality projects and working behind the camera. After being nominated for a Golden Globe for playing George Reeves in “Hollywoodland” (2006), Affleck wrote “Gone Baby Gone,” which became his directorial debut. Although Ben was not featured as an actor in the film, it received great critical reception leading some to believe that Affleck was better suited for directing rather than acting.

“Argo” (2012) and beyond
After writing, starring and directing his second feature film, “The Town” (2010), Affleck showed his improvement as a serious actor, as well as, his continued success as a director. Affleck’s latest project, “Argo” (in which he stars and directs) has already garnered a lot of Oscar buzz, as many critics are calling it one of the best films of the year. After several years of flops, Affleck seems poised to finally receive the respect he deserves as a filmmaker. If he does win an Oscar for “Argo,” Ben Affleck will have one more Oscar than acclaimed actor and friend Matt Damon, for those of you scoring at home.

What is your favorite Ben Affleck movie? Let us know in the comments below and on Twitter!