Matt Damon and Bill Simmons talked for almost 2 hours. Here’s what we learned

Matt Damon.
Jordan Strauss/Invision/AP, file
Matt Damon.

When Matt Damon joined Bill Simmons for the latest episode of the sports buff’s podcast, you knew the duo would discuss Boston, “Good Will Hunting,” and everything in between.

The two locals didn’t disappoint, chatting for almost two full hours during an episode of “The BS Report” released earlier this week, touching on everything from a lost ending to “Manchester by the Sea” to one magical night Damon spent hitting baseballs at Fenway Park.

The full episode is worth a listen, but here are five intriguing things we learned while listening to their conversation:

Damon got a special night of batting practice at Fenway Park.


When Fenway Park hosted the MLB All-Star game in 1999, Damon got to participate in the Celebrity Hitting Challenge with Red Sox great Jim Rice, one of Damon’s favorite players growing up. But the actor’s personal highlight came the night before the game when a former Sox employee let Damon, his dad, his brother, and a few friends hit batting practice for an hour in the middle of the night under the lights.

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“My dad was a pitcher in college, and I hit the wall, wood bat, off my dad,” Damon said. “We were driving out of there, and I said, ‘I’m never gonna need therapy, because that just happened.’”

Ben Affleck’s broken engagement helped “Good Will Hunting” get finished.

At one point during Damon’s time living in Los Angeles, he, Affleck, and another childhood friend, Soren, were discussing signing a new lease. But Affleck was engaged at age 22, and chose to move in with his then girlfriend, leaving Damon and Soren to rent a two-bedroom unit.

“Soren and I got this two bedroom on Curson [Avenue] off of Melrose,” Damon said. “And about two months later, Ben showed up with all his [expletive].”

Damon said what had been a comfortable living situation quickly became crowded, as Affleck filled their living room with his stuff and crashed on their cheap black leather couch.


“Ben’s 6’4″, the couch is probably 5’9″, so we’d go in in the morning and his legs would be hanging off the end,” Damon said. “I think that was one of the reasons — we were already writing ‘Good Will Hunting,’ but we finished it in that bungalow apartment in West Hollywood because we were like, ‘This is untenable.’”

Robin Williams struck a surprisingly good deal on “Good Will Hunting.”

Damon said that when Robin Williams signed on for his Oscar-winning role, producers were thrilled at how little they had to pay him. But Williams added a clause to his deal so that he earned significantly more if the movie did well at the box office.

“Robin made this incredible deal where if the movie made over $60 million he started to get some sort of escalating participation. He read [the script] and he just got it,” Damon said. “Everyone was like, ‘This is cool, we’re getting Robin Williams cheap,’ because he’s the biggest movie star in the world and I think he got $20 million a movie, and I think they paid him like $5 million.”

The film ended up earning more than $225 million worldwide, netting Williams a tidy payday.

“They were like, ‘Great, we’re winning here,’ and then it just turned out Robin crushed them,” Damon said.

“Manchester by the Sea” originally had a very different ending.


One of the topics discussed at length by Simmons and Damon was how the movie industry has fundamentally changed, such that movies like “Good Will Hunting” are rarely made today. According to Damon, digital technology and the almost-complete disappearance of the DVD market has caused Hollywood to spend 50 percent less in total on making films. The movies hurt the most were the mid-budget films, as studios shifted to big-budget superhero flicks with simple plots and safer profit margins.

“The movie that’s really gone is the $15 [million] to $70 million drama,” Damon said. “A lot of that has migrated to TV.”

Damon said he witnessed the difficulty of the disappearing middle-class movie while working as a producer for 2016’s “Manchester by the Sea.” Damon said that if they had more money to make the movie, director Kenneth Lonergan had planned an ending that would’ve made the critically acclaimed, Oscar-winning film even better.

In a flashback sequence, Casey Affleck’s character is on a boat watching whales with his now-dead children and brother (played by Kyle Chandler), along with his ex-wife (played by Michelle Williams). Even though Damon said the scene would have only taken one day of shooting and a little bit of luck with finding whales to film, the scene was scrapped due to budget.

“The camera’s pulling up, up, up, and it reveals all of these other boats all around it,” Damon said, describing the never-produced scene. “It’s all these other families that are watching these whales, right? This is one little story in this sea of stories. It was epic, and it was beautiful, and it tied the whole thing [together]. And we ran out of money. And it was like, ‘[Expletive]!’”

Damon was hurt by the way Ben Affleck was characterized early in their careers.

The perception of Damon and Affleck following the success of “Good Will Hunting,” according to Simmons, was that Damon was the “smart” one, while Affleck was the “dumbass.” That perception was aided by the fact that the year after “Good Will Hunting” was released, Affleck starred in the Michael Bay blockbuster “Armageddon,” while Damon was in the Oscar-winning “Saving Private Ryan.”

Damon called the whole situation “really hurtful.”

“I remember the first time seeing ‘Saturday Night Live,’ and they portrayed Ben as some [expletive] Neanderthal who literally couldn’t talk,” Damon said. “It was so offensive and so not true.”

Damon said that as relatively inexperienced actors, both he and Affleck were considering any roles they could get, and that he would have done “Armageddon” if he had landed the part.

“I would have done ‘Armageddon,”’ Damon said. “We had no idea where things were going to go for us. We needed jobs. I had lucked out and been cast in ‘Saving Private Ryan.’ Those movies came out the following summer … and then it was like, ‘Oh Matt’s the serious guy and Ben’s the big popcorn movie guy.’

“And it was just like, ‘No!’ We [each] would have done the other job,” Damon continued. “It was terrifically unfair, and then it took a long time for Ben to right that ship publicly.”

Kevin Slane can be reached at