Chris O'Rourke (vocals and guitar), Michael Galinsky (bass) and Rachael McNally (vocals and drums) started Sleepyhead in New York and soon published the trio of singles Play (Picture Book, 1991), Fairyboat (Picture Boo, 1992) and Punk Rock CIty USA (Slumberland, 1993) and the debut album Punk Rock City USA (Slumberland, 1993), altogher revealing the influence of Sonic Youth.

Starduster (Homestead, 1994) is instead already a mature work, in which the band finds a true voice, an angular folk-rock balladry that rewards lyrical and atmospheric gestures in a lightly psychedelic manner (What's Gonna Set You Free, Sick of Heaven).

Communist Love Songs (Homestead, 1996) is even better, despite a still uncertain style, as if the band did not know how to interpret its own compositions. The arrangements span acidrock and countryrock but rarely coalesce in a memorable groove or riff. Go West may be the standout track, mainly because the catchy melody and the energetic delivery support each other. The singers are a mixed blessing. McNally echoes both the epic Grace Slick (Ice Cream Cone, My Blooz) and the hoarse Kim Carnes (Yer Excellence), but mostly whispers away her vocal treasure. The songs tend to "talk" too much, and the counterpoint of the instruments does not adequately support so many words. I Love You The Rain weds a sunny refrain to a syncopated country-rock in the tradition of Grateful Dead. They have the skills to excel but they are still trying to organize them.

The EP Last Night Thinkin' (Sealed Fate, 1998) may have found the right approach with songs that are both melodic and robust (Wake-up Call, Boys Don't Lie).

Brighter Shore (Sealed Fate, 1999) displays influences from Yo La Tengo and Neil Young, which together weaken Sleepyhead's sound albeit bestowing an oneiric tone to the catchiest songs. The songs compete for the weirdest arrangement. Haflway between the Paisley Underground and garage-rock, the subtle crescendo of Late Night Thinking leverages O'Rourke's acid keyboards, dreamy whispers and McNally's convoluted, jazzy rhythm. Miss America, fundamentally an insinuating, bluesy tale in the style of glam-rock, features jazzy piano and dissonant jamming. The seven-minute work-out Gateway is a martial fantasia of glorious melodic bridges, celestial keyboard drones, jangling guitars.
These slowly mutating beasts are hard to make sense of. Song For The Pied Piper achieves a sublime fusion of Duan Eddy's twang, surf music, acid-rock and caribbean music, all wrapped in surreal vocal harmonies and middle-eastern chords. The noisier fabric of Poor Baby partially abandons the baroque posture of the album for a down-to-earth "Dylan-ian" ballad. The sprightly ska pace of The Box For Blue releases a Rod Stewart-esque soul ballad.
The roots of the band are hard to discern. Perhaps the light boogie of Citizen Band and the epic country of Like A Grizzly To Honey betray a bit of their musical background.
If Syd Barrett had not departed for another dimension, this is how Pink Floyd would have sounded in 1999.