With almost 30 albums under his belt, Loudon Wainwright III has been going strong since the ’70s, which makes it hard to figure out where to start digging into his catalog of funny, melancholic folk rock. So I’ll tell you where I started: Strange Weirdos, Wainwright’s 2007 album consisting of songs inspired by Judd Apatow’s comedy Knocked Up. These days, Knocked Up seems most memorable for introducing the world to the now-derided genre of “Seth Rogen making out with women who are out of his league,” but Knocked Up is also an excellent showcase for Apatow’s unmatched ability to blend crassness and sentiment, unearthing laughs and heart in equal measure. Apatow chose Wainwright to contribute to the film's soundtrack—as well as casting the musician, who’s been acting since appearing in M*A*S*H as a gynecologist—and Wainwright went to town with an album that’s clever, tender, warm, and sharp. Wainwright’s from-the-gut songs on Strange Weirdos (particularly his take on Peter Blegvad’s “Daughter”) hit hard, but when taken altogether, they come with a grin and a quick elbow to the ribs. “When it’s gray in LA/ it’s much better that way,” Wainwright sings. “It reminds you that this town’s so cruel/ yeah, it might feel like fun when you're sportin’ sunglasses/But really you're one more fool.”

by Erik Henriksen