There’s an outtake from Season 3 of HBO’s Mr. Show with Bob and David in which Karen Kilgariff, then a performer on the Nineties sketch series, mocks herself by furrowing her brow and shaking her first at someone off camera after flubbing a line. It’s throwaway by design, but it sticks with the viewer and underscores Kilgariff’s ability to turn random moments of self-awareness into pointed, memorable humor.
Kilgariff’s Live at the Bootleg, recorded in September at L.A.’s Bootleg Theater, gives her even more chances to bring out the knives in song form—an accomplishment in a genre not always known for its poignant gifts to the comedy canon. On album opener “I Want to Win,” we learn more about her in two and a half minutes than we do from entire sets of other standups.
She’s jealous of Tina Fey (her job, her money, her glory) and ready to kill the next person who tells her to watch Modern Family. But she’s also doubtful about the possibility for true love and wistfully resigned to its fleeting nature. Communicating these clashing ideas in the same short, sprightly song is an impressive magic trick, and it’s one she pulls off throughout the album.
Kilgariff’s a fine singer, with a wavering, vulnerable voice that falls somewhere between coffee shop balladeer and demented children’s entertainer. Her saccharine delivery complements the murky timbre of her acoustic guitar and sells the jokes against the often bleak, angry lyrics. It’s not Garfunkel and Oates, where the twists are dull and predictable, and the music is painfully cutesy. Nor is it a female Tenacious D, where the joke is in the band’s ego. It’s multi-layered observational comedy with recurring (but not overbearing) feminist themes set against metaphor-laden love songs. Again, not an easy task.
Five of these tracks appeared on Kilgariff’s 2011 EP Behind You, but given their quality and the life a few of them have taken on through podcast appearances, it’s perfectly justifiable to include them on Bootleg. They don’t feel tacked on or dated, especially since the subject matter and styles jump around so much. The connective tissue is Kilgariff’s alternately gracious and catty between-song banter, which proves her ability to play the crowd at least as well as her instrument. “I’m treating this like a Behind the Music,” she says after “Solid 9,” “so if you don’t want to hear it, get the FUCK out right now.”
The banter is so charming and loose that it’s hard to imagine Kilgariff doing either a straight stand-up set or a music-only set. The stories are equally as important as the songs. And the songs are pitched perfectly: not complicated or showy, but also meatier than the basic, incidental backing tracks of Zach Galifianakis’s ivory tickling or Demetri Martin‘s meandering acoustic work. Kilgariff discounts her guitar skills a few times, but songs like “Drink Your Way Through Christmas” prove she’s at least confident enough to tackle propulsive, upbeat chord progressions while hitting the vocal high notes.
A press release for the album notes that musical comedy is “rarely done right,” which is a sentiment (and sales tactic) that could have easily backfired had Bootleg not been so great. But given that the titans of the genre, from the Smothers Brothers to Flight of the Conchords, have proven there’s no single way to work humor into melodies, it’s encouraging that Kilgariff’s own take on the genre sounds so fresh and vital.