Matt Damon: It Was "Hard for Me" to Watch Ben Affleck's Rough Years

Matt says it wasn't easy seeing Ben struggle during a career downswing, but he feels "vindicated" now that Affleck is back with a vengeance

Matt Damon and Ben Affleck's careers both started out with a bang when they starred in and cowrote the 1997 drama Good Will Hunting -- for which they won best screenplay Golden Globes and Oscars. They both went on to star in some great films -- Saving Private Ryan and The Talented Mr. Ripley for Damon, Shakespeare In Love and The Boiler Room for Affleck -- but the early 2000s marked a turn for the worse for Affleck's public persona.

After a series of public relationships and breakups (remember Bennifer?) and box office disasters (hello, Gigli), Affleck had become something of a Hollywood joke. Damon's career was booming during that period, considering he had landed the lead in The Bourne series and was also starring in the Ocean's trilogy. In an interview with ShortList.com, Damon reveals just how difficult to it was to watch his best friend struggle during that time.

"That was really hard for me to watch as his friend, because I didn't think it was fair to him," Damon says of Affleck.

Fortunately, Affleck's career has made a serious comeback. The 39-year-old started directing (he has two acclaimed films, Gone Baby Gone and The Town, under his belt), got married to Jennifer Garner and has two daughters -- Violet Anne, 6, and Seraphina Rose Elizabeth, 2 -- with a third child on the way. Damon says it's nice to see Affleck back on top.

"It's more of a relief to me, to be honest. As his writing partner, I know how great he is. I always knew that better than anybody, so now I just feel vindicated," he shares. "I'm not at all surprised, but I'm glad to see him doing so well and it's turned back the way it should be. Everything is right with the Force again."

But just because Affleck's slump is a sensitive subject doesn't mean it's off limits for a few Daredevil jokes here and there. "Oh man, we've always been at that stage. We never left that stage," Damon says.

The two haven't worked together since 1999's Dogma, but 41-year-old Damon says they have plans to reunite again in the future. He promises they have a "couple of things we're developing" and they have a "deal together over at Warner Bros." One of those projects is the based-on-real-life Yankees movie The Trade that teams Damon and Affleck with Ben's younger brother, Casey Affleck. The movie, about two Yanks pitcher's who swap wives (seriously!) might even put Damon in the director's seat for the first time.

"I don't know how it'll come together, acting and directing, but Casey and I have decided to write it together," Affleck told MTV News last year. "Once the script's kind of ready, then it's like: Who's doing what? What's the time frame? Matt, me, Casey directing? Particularly for Matt, he's had this extraordinary career where he's worked with these great directors. He's a great director who just hasn't directed a movie."

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