Loudon Wainwright III: songwriting, humor, inspiration and the late-Tom Lehrer (Full Interview)

Acclaimed singer-songwriter and professional funnyman Loudon Wainwright III spent his 79th birthday diving deep with IPR's Tony Dehner at the inaugural Iowa City Songwriters Festival on September 6, 2025. The pair discuss everything: Wainwright's storied career in music, film and television (including his roles on "M*A*S*H" (13:17), the Judd Apatow projects 'Undeclared,' 'Knocked Up' (14:22) and his own Christopher Guest-directed Netflix special 'Surviving Twin' where he reimagined his own father's writings), his creative children, writing a song about O.J. Simpson for NPR in 3 days, the "New Bob Dylan" Club (16:07), Charlie Poole, "I Wish I Was A Lesbian," "Dead Skunk" (4:40) and, of course, songwriting. Wainwright wowed with an a cappella performance of the late-Tom Lehrer's 1959 satirical classic "Oedipus Rex" (22:11), and took no prisoners with his wisecracks. "Johnny Depp, I think, wants to be a singer-songwriter," said Wainwright. "He can try. It's harder than selling men's cologne, Johnny" (16:29). Wainwright even took time for an audience Q&A following Tony's interview (30:27). Audio/Video by Lucius Pham.