Sleepyhead was formed in a basement room at NYU’s Brittany dorm in the fall of 1989 by drummer/vocalist Rachael McNally, bassist Mike Galinsky and guitarist/vocalist Chris O’Rourke. They released their first 7″ single, the Kramer-produced “Play,” in 1991 on Picture Book Artifact Records. Four full-length albums followed, on three different independent record labels. Punk Rock City USA was released by Slumberland Records in 1993, followed by Starduster (Homestead 1994), Communist Love Songs (Homestead 1996), and The Brighter Shore (Sealed Fate 1999). They toured the United States and Europe throughout the nineties, sharing the stage with such legendary bands as Polvo, Half Japanese, Yo La Tengo, The Grifters, The Dambuilders, Nation of Ulysses, Helium, Royal Trux, Antietam, Luna, Versus, The Magnetic Fields, and Dungbeetle.

After a move to Boston and a few lineup changes, the band released Wild Sometimes on the esteemed Carrot Top Records label, which sadly closed up shop in 2016. Now, with a lineup including multi-instrumentalist Derek van Beever and bassist Ani Somasundaram, the band has found a new home with Dromedary, releasing the single “Hoping That You’re Lonely” b/w “Busted Lullaby” in advanced of a full-length coming in 2025.