Thanks to his recent shift to directing, the Artist Formerly Known as One-Half of Bennifer has risen like a phoenix from the Gigli ashes and gone on to cultivate a compelling film career, including a great performance in this weekend's Gone Girl. But for a minute there, things got weird. The success of Good Will Hunting let Ben Affleck ride right into the world of questionable (and I mean questionable) film choices for a solid few years. His movie roles over the past two decades run the gamut of quality, but at least nine have been particularly odd. Not bad, just … different.
9. Gigli (2003)
The tale of Gigli is a cautionary one, a story that evokes memories of turkey jokes and celebrity-couple portmanteaux. Believe it or not, though, compared to the rest of the Affleck-ography, Gigli is actually the least bizarre. At the time, the actor was bouncing from genre to genre, dabbling in rom-coms and action films, and had yet to plunge into the type of filmmaking that would bring him back into the Academy’s good graces. Of course he would star opposite his fiancée. When you’re flailing, you don’t ask questions.
8. Forces of Nature (1999)
This is way weirder than the Gigli phenomenon. In 1999, Ben Affleck could do no wrong. Having just come off '98’s Good Will Hunting win, his appearance in '99’s Shakespeare in Love, and even his turn in 200 Cigarettes, it was odd to see Affleck pick such a formulaic romantic comedy so soon in his career.
7. Jersey Girl (2004)
On paper, this movie makes sense: Ben Affleck plays a dad (believable) who loses his wife (played by Jennifer Lopez), and raises his daughter on his own (okay) before falling in love with a video-store clerk (played by Liv Tyler). With Lopez literally and proverbially out of the picture, Jersey Girl could’ve represented Affleck’s turn as a man ready to refocus on acting — or at least on indie films, since it was written by longtime collaborator Kevin Smith. But no. Instead, a watered-down Gigli follow-up that made audiences question why Ben kept acting alongside his romantic partner.
6. Man About Town (2006)
We know that Ben Affleck can take on serious roles. We also know Ben Affleck can do romance. And we know that any movie co-starring John Cleese has the potential to be very good. With Man About Town, the combination of all three was ... released directly to DVD. The failure of this movie was a good indication of the mess Affleck had made for himself, career-wise, in the first few years of the 21st century.
5. The Third Wheel (2002)
This is a movie about a homeless man who interrupts a first date between Luke Wilson and Denise Richards. Affleck does not play the homeless man. Affleck plays the best friend. Affleck is the fourth wheel.
4. Daredevil (2003)
2003 wasn’t Affleck's greatest year. Considering that roles like O’Bannion (Dazed and Confused) and Chuckie Sullivan (Good Will Hunting) had cemented his typecasting as a smarmy bully, playing the title role in a superhero movie could have been meant to combat that stereotype. “See? He can be heroic! He can be the guy we root for!” And he is, 11 years later.
3. He’s Just Not That Into You (2009)
He’s Just Not That Into You was perhaps the worst result of the post–Love Actually multi-star relationship comedy, offering us Affleck, Bradley Cooper, Scarlett Johansson, Jennifer Connelly, Jennifer Aniston, and several others in a less-smart, "subversive" take on how relationships "work." By 2009, Ben Affleck had restored his reputation … only to sign on to play a boyfriend who can't commit until his girlfriend agrees that marriage is stupid.
Unless this is how Gone Girl starts. Then I take it all back.
2. Surviving Christmas (2004)
Ten years ago, Ben Affleck played a money-hungry ad exec who infringes on the Christmas of the family who now lives in his childhood home. Through them, he (somehow) finds the true meaning of both the holiday and his life. Surviving Christmas was almost — almost — as weird as Affleck would ever get. The following year saw Affleck return to audiences’ graces as he began to embrace more interesting roles and would go on to direct his first movie, the well-received Gone Baby Gone.
1. Runner Runner (2013)
Why, after the success of Argo and The Town, would Ben Affleck even think about helping indulge Justin Timberlake’s acting dreams? Why would he agree to play a forgettable online-gambling kingpin called "Ivan Block"? Did he need a break? A vacation? What could we have done to stop this from happening? What did we need to say? Who tricked him? This movie was made in 2013! Which meant that, as recently as last year, Ben Affleck looked around at his life and all his awards and all the A-list projects begging him to join and simply thought, Sure, I’ll be in a Justin Timberlake movie. Absolutely.