The Rewatchables
‘Good Will Hunting’ Live From Boston With Bill Simmons, Ryen Russillo, Chris Ryan, and Sean Fennessey
Tue, 01 Apr 2025
Live from the House of Blues in Boston, The Ringer’s Bill Simmons, Ryen Russillo, Chris Ryan, and Sean Fennessey gotta see about a pod after rewatching the 1997 Boston classic, ‘Good Will Hunting’—starring Matt Damon, Ben Affleck, Minnie Driver, and Robin Williams. Watch this video and much more on our Ringer Movies YouTube channel! Producer: Craig Horlbeck Video Producers: Ronak Nair, Jack Sanders Learn more about your ad choices. Visit podcastchoices.com/adchoices
Chapter 1: What is the significance of 'Good Will Hunting' in film history?
Chapter 2: What makes Boston movies unique?
This is like the math scene.
Sean's like, you know how easy this is for me?
It's a fucking joke. Don't put a whiteboard in front of me, man. I got markers. It happened again one year later with Life is Beautiful. Roberto Benigni did it.
That's a tough one. And you know who brings that? Harvey Weinstein. Yeah. Well, we have two big Oscar debates that come out of this.
Do we?
Yeah, we do. Buckle up, Ursula. It's coming up next! Jack Nicholson wins for As Good As It Gets. The other nominees were Matt Damon, Good Will Hunting, Robert Duvall, and The Apostle. Peter Fonda and Uli's Gold. That was the other choice for tonight. And then Dustin Hoffman for Wag the Dog. And all these years later, I just think Damon should have won. Agree.
And As Good As It Gets, which was really good when it came out. It was James L. Brooks, and it was a thing. Helen Hunt got nominated, too. I just don't think it's aged well as a movie. And it makes me mad that Matt Damon didn't win. CR?
Damon's unbelievable in this movie. Do you ever think about him writing his own speeches, though? Do you ever think that that should be some sort of demerit? Because if Jack Nicholson could always just write his own scenes... Is this you justifying never having won an award? No. If you write all your own material? But I think Damon is like...
Even scenes that I thought of as Robin Williams scenes, like Damon is unbelievable in them. So he is very deserving. I thought he was awesome. What do you think, Priscilla?
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Chapter 3: Why are Matt Damon and Ben Affleck important figures in Hollywood?
And just like the formation of the group, the smart one, quiet one, loud one, dumb one, like perfect The Beatles right there.
Yeah, definitely Matt and Ben Industries. You know, the idea of them being this iconic duo now for 30 years running, which is amazing that it lasted this long and usually doesn't work out that way. And then I think this is the conversion of Robin Williams' legacy from comedy person to iconic actor. And if he doesn't have this movie, even though he did plenty of dramatic parts...
He's really thought of more as a performer and not Mork. Even if he had done Dead Poets and he had done What Dreams May Come or whatever.
Yeah, because he was struggling a little bit from an IMDb standpoint. He made that movie Jack. He made that movie, What Dreams May Come, with Cuba Gooding that you just mentioned. He was a little bit of a slump.
Although, if not for Jack, he might not have done this movie. True. Because he asked Francis Ford Coppola, who the fuck are these guys? Because he had just made Jack with Francis Ford Coppola. And Francis Ford Coppola cast Damon as the Rainmaker. So that was a critical, even though Jack sucks. Sorry, Jack.
Sorry, Jack. Look, that's the right answer because I was watching the Oscar acceptance speech this morning. It's great.
That's a good message.
I mean, it looks like a bit.
Yeah.
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