Kevin Smith has been known for working with Ben Affleck and Matt Damon during the course of his career, but I recently learned the two were actually involved in the meet-cute between Kevin Smith and his wife. At least sort of. The story is a twisted yarn that also includes the Oscar-winning movie Good Will Hunting and Chris Rock getting out on the town. It's a crazy story, truly. Let me walk you through it.
A few years back, The Ringer’s Katie Baker wrote a piece for Mallrats’ 30th anniversary, noting it was Smith that helped convince Miramax it needed to get Good Will Hunting off the ground with Ben Affleck and Matt Damon attached. More recently, when Damon spoke with Travis and Jason Kelce about getting paid $600k with Ben Affleck on their first movie, only to need a job within a year, the writer gave us some wild backstory on X about this era and how it led Kevin Smith to meet his wife.
Let me set the scene here. Smith at the time had already been famous for a while when this story commenced thanks to movies like Clerks and Mallrats. The cat story that comes up in Mallrats, which Affleck appeared in, is similar to one told in Good Will Hunting just a couple of years later, and Baker asked Smith about it.
Apparently it’s just a side note in the even crazier story of how he met his wife.
I was in the culture at that point with Clerks, and maybe they were just like, ‘Oh yeah, write some dialogue like [the cat thing].’ But no. But that was how I met my wife Jennifer. Because Miramax was catching a lot of shit. And there was no Internet really, but in the entertainment media, you know, there were a lot of people like, ‘This Good Will Hunting should get nominated for a screenplay!’
This was in 1998, after Good Will Hunting had already come out and made a name for itself. In fact, Affleck and Damon have previously credited Smith for getting the movie made. At this point, though, Affleck and Damon were the cool kids in town, though Smith was also a big name with sway who happened to be pals with the two Hollywood newcomers. (His movie, Chasing Amy, also came out the same year as Hunting.) As the Oscar race heated up, he said so did the rumors.
And then Hollywood started getting real cutthroat about the Oscars and shit. And so people started spreading this rumor like, ‘Well I heard William Goldman did a draft of Good Will Hunting.’
As cool as The Princess Bride writer is, that was not good news for the movie studio trying to promote Ben Affleck and Matt Damon. So, they asked Kevin Smith to step in and talk to a journalist about what was going on. The gist was “the boys” had talked to Goldman and “picked” his brain, but he didn’t write a draft for them.
Ben and Matt said they sat around just fuckin’ picking William Goldman’s brain about his movies for the next hour. So, the press is starting to be like, ‘I don’t know if these boys did write the screenplay.’ And so Miramax goes, ‘You got integrity. We’re gonna send you an interview where you’re gonna talk about your comic books and you’re about to make Dogma and the year you’ve had with Chasing Amy. But primarily there’s a sidebar we’re really interested in about Good Will Hunting. And you’re gonna go vouch for the boys that they did indeed write the screenplay.
Smith nearly forgot about this interview he'd committed to. He’d been working with Chris Rock on Dogma while Rock was also working on Lethal Weapon 4 (one reason we know it was '98 at this point), and Rock had been trying to get him to go out on the town.
After we were done, he was like, ‘What are you gonna do for the rest of the day? You’re in Hollywood, you gotta do something.’ I said, ‘I might go to the Details Young Hollywood party, Ben and Jason Lee are going.’ And he goes, ‘No, no, you gotta get a hooker, man!’ And I was like, ‘Oh no, I’m not –I’m not a hooker guy.’ And shit like that. He goes, ‘You’re wasting Hollywood, Kevin.’
Now, Kevin Smith’s wife is Jennifer Schwalbach, who worked at the time at USA Today. He said he had a pretty specific picture of what a journalist at USA Today would look like, and it was not what young or hip like she looked like when she came and knocked on the door.
It was a knock on my door; open my door; and it was not, like, a middle-aged woman. There was this like really young, 25, 26-year-old girl in like leather jacket and jeans and shit like that. Insanely attractive. And the first thought I had about the woman who I’d marry was, ‘Oh my god, Chris Rock sent me a hooker.’
I don’t think anything could get more Hollywood than this story, until Kevin Smith pointed out to Baker that without Affleck, he never would have met his wife. He concluded:
I realized at this point that if I don’t cast [Affleck] in Mallrats, we don’t become friends. He doesn’t ask for my help on Good Will Hunting. And because of Good Will Hunting going to Miramax, they never ask me to go defend the movie, and that’s where I meet Jennifer.
Good Will Hunting went on to win the Oscar at the 1998 Academy Awards; Ben Affleck and Matt Damon's speech from the event is legendary. Chris Rock went on to make Lethal Weapon 4; it's reception was OK, though plenty of fans of the franchise fondly remember it. Ben Affleck and Kevin Smith later had a falling out, then rekindled their friendship a few years later in 2022; Smith owned Ben Affleck's house for years before selling it in 2023.
Kevin Smith and Jennifer Schwalbach went on to become on of the enduring celebrity marriages. They were married by 1999, had Harley Quinn Smith that same year, survived Smith's heart attack, and celebrated their 27th anniversary just a few months ago. To think about it all starting with William Goldman, Good Will Hunting, and a goof around conversation with Chris Rock about a hooker is... pretty crazy honestly.
