Ben Affleck's Hollywood career has played out like a rollercoaster. After winning an Oscar for Good Will Hunting in 1998, the Boston-raised actor slowly, painfully plummeted to rock bottom (2003's Gigli). Three successful stints as a director have helped reverse his misfortunes, but his high-profile divorce from Jennifer Garner has once again put his future in jeopardy. In light of that scandal, we're taking a look back at his long, but shaky, career as an actor and director.




Rise: Good Will Hunting (1997)

After acting in bit parts for over a decade, Ben Affleck finally hit big in 1997 with the release of Good Will Hunting, which he co-wrote and co-starred in with his best friend, Matt Damon. The film—about a Harvard janitor (Damon) who is secretly a math genius—was an immediate box office and critical smash, earning rave reviews and, eventually, a Best Original Screenplay Oscar for Affleck and Damon. In an overnight success story that could only happen in Hollywood, Affleck and Damon were suddenly Hollywood's most sought-after men

Rise: Hollywood Leading Man


With movie offers piling up post-Good Will Hunting, Affleck and Damon each tried their hand at playing one of Hollywood's most coveted roles: Leading Man. In Affleck's case, he stuck mostly to high-profile Hollywood films, ranging from prestige Oscar winners (Shakespeare in Love), to romantic comedies (Forces of Nature), to male-driven thrillers (Reindeer Games; Boiler Room) and blockbusters (Armageddon, which, to this day, remains his most successful movie). Not every movie he starred in was a success. (Lest we forget Bounce.) But by the end of 2000, audiences and critics remained patient as they waited to see how his career would shake out.


Fall: Pearl Harbor (2001)

Michael Bay's World War II drama Pearl Harbor proved to be a blessing and a curse for Affleck. On one hand, the film was an undeniable box office hit, ranking seventh among the year's top grossers. On the other, it was a critical disaster. For his role in the film, Affleck earned some of his worst reviews to date and, perhaps most embarrassingly, his first Razzie nomination for Worst Actor. After Pearl Harbor's release, you couldn't say Affleck's name without laughing a little.


Fall: Rehab

A couple months after the release of Pearl Harbor, 29-year-old Affleck voluntarily checked himself into Malibu's famous rehab facility, Promises, reportedly with the help of then-reformed bad boy, Charlie Sheen. Affleck sought treatment for alcoholism—his first of many personal woes to come.

Fall: Jennifer Lopez

While filming the movie Gigli (we'll get to that one in a second) in 2002, Affleck fell head-over-heels in love with his leading lady, singer-actress Jennifer Lopez. Thus began the biggest and most-written-about Hollywood romance of the new millennium. Affleck and Lopez were almost immediately referred to as "Bennifer" by the tabloids, who covered the couple's every move to an exhaustive and, eventually, tiresome degree. A quickie engagement at the end of the year officially made them overexposed in the eyes of the public. Naturally, everyone got sick of hearing about them.


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