The Greenberry Woods was a power-pop quartet formed in 1989 by songwriters Matt Huseman and Ira Katz while students at the University of Maryland. They were later joined by Huseman's twin brother Brandt Huseman on bass and drummer Miles Rosen. Named for a suburban Maryland housing development, the band seemed destined for big-time success—with critical acclaim[citation needed], a major-label record contract, and an ever-growing fan base. However, the band released only two albums before disbanding in 1996.

Upon graduation from the University of Maryland, the band moved to Baltimore. The band hired manager John Lay, whose previous clients included Squeeze and Robyn Hitchcock, Lay’s industry connections helped the band secure a deal with Sire Records in February 1993. Their debut album, Rapple Dapple, was released in 1994, with the single "Trampoline" receiving healthy radio airplay. Supporting tour slots with such acts as Debbie Harry and the Proclaimers followed. The Greenberry Woods performed at the 1994 HFStival, May 14, 1994, RFK Stadium, Washington, DC.

When Sire merged with Elektra Records, the label’s support for the band dwindled, and tensions arose over Splitsville, the Husemans’ side project with Paul Krysiak. The individual ambitions of three songwriters took its toll on group harmony during the recording of their second album Big Money Item, and Sire released the band from its contract in 1996, leaving the Husemans free to pursue Splitsville; Katz, meanwhile, formed a new band, Wonderfool, while Rosen quit music to become a mortgage broker.