Ben Affleck picks his favourite Ben Affleck movies
Alongside his early career partner Matt Damon, Ben Affleck became an overnight star in 1997 following the success of the duo’s debut movie, Good Will Hunting. Damon and Affleck co-wrote and starred in the classic Gus Van Sant direction, earning them the Academy Award for ‘Best Original Screenplay’ for their efforts. Consolidating the monumental achievement, Robin Williams also won the Academy Award for ‘Best Supporting Actor’ for his role as therapist Sean Maguire.
“Ben has always had an incredible charisma. People are just getting introduced to it through film,” Damon told The Los Angeles Times while reflecting on their friendship in 1999. “It’s hard to think of your best friend as a movie star, but the fact that he is [stems from] the extent to which parts of the real him come through. He is somebody that everybody wants to be around.”
Though their career paths have parted and converged several times over the past 25 years, Damon and Affleck have enjoyed a sturdy friendship and reunited in 2022 to collaborate on Air, the latter’s direction covering the story of basketball player Michael Jordan and his famous association with Nike.
Speaking with People magazine in April, Damon discussed the importance of his friendship with Affleck. Damon stated that their bond is “everything to me” and that his life would be “unimaginably harder” without his childhood buddy. “It’s been really helpful to check in with Ben throughout this whole surreal process over the last 25 years,” he added.
It comes as no surprise that, when asked in 2021 to name his favourite three of his own movies, Affleck saved a spot for his 1997 debut with Damon. “Do I star or direct? Does it matter?” Affleck asked podcast host Bill Simmons.
“Oh, that’s interesting. I think it can be either. Let’s say either,” Simmons replied.
“Ok. Gone Baby Gone, The Town and Good Will Hunting,” Affleck asserted without hesitation.
While the podcast predates Air, these choices are undoubtedly prominent milestones in Affleck’s career. Gone Baby Gone, released in 2007, marked Affleck’s directional debut. He also co-wrote the screenplay with Aaron Stockard, based on the 1998 novel of the same name by Dennis Lehane.
Affleck cast his younger brother, Casey, in the movie alongside Michelle Monaghan and Morgan Freeman. Gone Baby Gone was a resounding success both critically, promising a bright future for Affleck behind the camera.
Three years later, Affleck co-wrote, directed and starred in The Town. The successful crime drama was an all-encompassing labour of love based on Chuck Hogan’s popular 2004 novel Prince of Thieves. The story, based on true events, follows Affleck’s character, Douglas ‘Doug’ MacRay, who commits a bank robbery with a group of childhood friends before strangely befriending one of the hostages.
Watch the trailers for The Town, Gone Baby Gone and Good Will Hunting below.
