14 Apr 2026

Kent Goes to Chelmsford: Episode 5

by Jack Pendarvis

Kent Osborne lives in Vermont. Jack Pendarvis lives in Mississippi. The two old friends, each sleep-deprived and noticeably loopy from traveling all day, met up at a hotel bar in Burbank, California, to discuss Kent’s role in the 1992 drama School Ties.

Episode 5: The Five Jerks

JACK: So your first day on the set. So, okay. They say, “Okay, Kent, you’ve got the part. And you need to go to Chelmsford.”

KENT: Yeah.

JACK: And you were like, “Chelmsford?”

KENT: Yeah.

JACK: “I’ve always wanted to see Chelmsford!”

KENT: You know, I’m trying to remember now. I feel like I went up for a weekend and met everyone, and we rehearsed in the hotel. And then I went back to New York. And then I went back up for two weeks when they were filming, I think. Because when I first went up, all the—Matt Damon and Ben Affleck and… they were all staying at the Chelmsford Inn. They were all coming from L.A., I think. And we went up from New York for a couple of days to rehearse and meet everybody.

JACK: Who’s “we”?

KENT: It was like me and four other actors. And I’m trying to—one of the guys was named Jayce Bartok. And he ended up—he had been in a couple of other movies. Another guy was named Sean Kent, which was strange, because I was Kent Osborne. And there were maybe two other guys. And we were like—there was the main cast and then there was “There’s five other people in this classroom that have a couple of lines here and there.” Or, you know, we were there to… “The cast is too good-lookin’! We need some, like… some…”