Matt Dillon and Diane Lane as the couple from “Oaks.”
Some of my favorite things ever are the S.E. Hinton books and the movies made from them (The Outsiders, Rumble Fish, etc.). Matt Dillon and Diane Lane have a knack for looking good while getting into trouble, or at least not being far from it.
Harry Dean Stanton as the priest in “How a Resurrection Really Feels.”
I like the idea of a fatigued priest. He’s had a good run, but he just can’t get quite as excited for all of it anymore. In this song, the priest laughs at the most dramatic moment and also surrenders his pulpit.
Katherine Heigl as the girl in “Chips Ahoy!” and “The Weekenders.”
Katherine Heigl is, in my mind, the queen of the Romantic Comedy That I Can Only Watch on an Airplane. She’s especially good at the first part of the rom-com where the male lead finds her hard to like. She does this very believably. At the end of “The Weekenders,” I say, “It’s not going to be like a romantic comedy,” and this seems like something you’d have to remind Heigl about.
Gena Rowlands as herself in “Slapped Actress.”
This song was written about Opening Night, the John Cassavetes movie. I was really obsessed with it when we were making the Stay Positive record. It has this whole “all the world is a stage” vibe that ends up getting a bit spooky actually. Gena Rowlands was so good in all the Cassavetes movies, but I especially love her in Minnie and Moskowitz.
John Lovitz and Whoopi Goldberg as the couple from “The Ambassador.”
I loved this pairing in Jumping Jack Flash and again in Rat Race. I think they could bring a certain lightheartedness to the heavy situation of the song. Or maybe I’m crazy.
SEE IT: The Hold Steady plays Wonder Ballroom, 128 NE Russell St., with Cheap Girls, on Thursday, July 17. 7:30 pm. $23 advance, $25 day of show. 21+.