Ones of Matt Damon’s 2026 movie releases, The Odyssey, couldn’t stop breaking records after its debut this past July. It became the second highest-grossing movie of the year with a worldwide haul of $1.8 billion. It’s also the highest-grossing R-rated movie ever and the 11th highest-grossing movie ever. At present, Damon’s name is also being mentioned amid awards season conversations. Still, as the star comes off his big year, he’s speaking honestly about what he considers to be the low points of his career.
The Good Will Hunting star was recently asked when he knew The Odyssey would be a hit, and he admitted that moment came when he saw the movie for himself. Decades earlier, Damon had those same instincts, as he explained to GQ. However, in those cases, the results weren’t nearly as strong as they are now. While discussing one particular slump, Damon named one of the films he had on the docket in 2000:
The first time was before The Bourne Identity came out. I had done The Legend of Bagger Vance with Will [Smith] and Charlize [Theron], and that movie didn’t do well. And Will was, as he is now, the biggest star. And so it’s like, it’s not Will’s fault. [Laughs]
While The Legend of Bagger Vance may have had one of the best golf scenes in Hollywood history, it was definitely a box office bomb, grossing $39.5 million globally against a reported production budget of $80 million. Not to mention, the sports-drama film has low critics’ score of 43% on Rotten Tomatoes. In the long run, it didn’t hurt the careers of Damon, Smith or Theron, but I can understand why the Bourne star would’ve been shaken by the reception at that time.
Damon, unfortunately, experienced another setback after the release of Bagger Vance. There’s another failed movie of Damon’s that he’s still not over, and it was released in 2000 as well:
And then I did All the Pretty Horses with Billy Bob [Thornton], and that was a whole fraught experience. There were different ideas between the studio and between Billy Bob about what the movie should be, and so it ended up getting cut in a way that wasn’t to Billy’s liking and it didn’t do well. And so I had had these misses. And so there was this stretch where the phone just didn’t ring. The silence was…. It was a real rose-colored lenses coming off.
I can imagine how frustrating that must have been to envision what you wanted your movie to be, only for the studio to take over. With that, it’s hard not to wonder what could have been if Billy Bob Thornton had had his way. Ultimately, All the Pretty Horses was another bomb for Damon, as it made only $18.1 million worldwide on a budget of $57 million. As for its critics score on Rotten Tomatoes, it’s at 33%, as of this writing.
Considering the Saving Private Ryan star’s immense success, it’s now somewhat wild to think about Damon worrying about his acting career, but it happens. He’d later experience a huge lull with no job offers, until Steven Soderbergh approached him about The Informant! The Ocean’s alum was so happy that he even offered to write the screenplay. While Scott Z. Burns ended up with the screenwriter role, Damon was still honored to be offered this leading role after a long career stretch.
It’s so refreshing that Matt Damon has no problem looking back on the rougher points of his career. It’s also not unheard of for actors to look down on their own movies, but Damon speaks more diplomatically about Bagger Vance and All the Pretty Horses. I can imagine setbacks being hard to think about, but I get the sense that they’ve served as fuel for his career. And just look at him now. He’s the lead of one of the biggest movies of all time and could even land himself some awards over the next few months.
On that note, The Odyssey is now available now available to rent on various digital platforms.
