The song's music video is presented as a mockumentary about Mann's past as vocalist for 'Til Tuesday. In the clip a decision is made to recreate the music video for the group's best-known hit, "Voices Carry
," scene by scene, against the wishes of Mann. The visual was directed by comedian Tom Scharpling and features Mad Men's
Jon Hamm as well as his comedy partner, Superchunk drummer Jon Wurster, who plays Mann's love interest. Also featuring are punk musician Ted Leo and former 'Til Tuesday drummer Michael Hausman, who is now Mann's manager.
Mann told Spinner
: Tom Scharpling is the guy who directed it. He's a comedy writer. His instincts are so dead on and he felt like there was sort of a nostalgic interest [in the "Voices Carry" video] but also a ridiculousness factor - especially if the setup was that I was coerced into it. He thought [that] was really funny and I totally agree. And having Jon Wurster, who's a good friend of mine, play the guy in the [video]. He's so funny and he's got this high voice so it's even more ridiculous. I thought it was a real inspired idea."