Sleepyhead was formed at NYU 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. 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). Around the time their fourth album was released in 1999, Rachael and Chris got married, and Mike Galinsky had moved on to a successful career in filmmaking. Dan Cuddy (The Special Pillow, ex-Hypnolovewheel) joined Chris and Rachael on bass. Rachael and Chris moved from New York to Boston in 2002. By this time, they had begun recording a new album with producer Mike Deming (Pernice Brothers, Apples in Stereo, Beachwood Sparks, Lilys), at Deming’s famed Studio 45 in Hartford, and subsequently Enfield, CT. In 2004, bassist/vocalist/keyboardist Derek Van Beever joined the band and they’ve been playing shows in Boston, Providence, and New York, and beyond ever since. They released Wild Sometimes on Carrot Top Records in 2014. In 2018, Sleepyhead celebrated the deluxe double-vinyl reissue of Starduster and Communist Love Songs in April 2018 on Drawing Room Records. They are working on a new album at Q Division Studios in Boston, which they plan to release in 2019.