Given Trip Shakespeare's connections in the music industry, it didn't take long for Semisonic (which had initially formed under the name Pleasure) to secure a record deal with Elektra. Before the band could record, however, management reorganization at Elektra's headquarters resulted in the termination of Semisonic's contract. The band bounced back in 1995 by signing with MCA and releasing a self-produced EP, Pleasure. The Great Divide followed in 1996, marking Semisonic's full-length debut and garnering a favorable review from Rolling Stone, which deemed it "a record of simple but sparkling modern pop." However, it was the musicians' sophomore effort, Feeling Strangely Fine, that marked their major breakthrough in 1998. "Closing Time" topped the modern rock charts, "Secret Smile" became a Top 20 hit in the U.K., and Semisonic enjoyed a brief flash of megastardom as the millennium drew to a close.

All About Chemistry, the band's third album, was issued in early 2001 and yielded additional U.K. hits, but the record failed to maintain the group's popularity in America. Semisonic wrapped up the year by contributing "Over My Head" to the soundtrack for Summer Catch, a baseball-themed teen flick, and covering Wings' "Jet" for a Paul McCartney tribute CD entitled Listen to What the Man Said. Dan Wilson also took time out to lay the brickwork for his solo material, playing a slew of dates around the Midwest, while his brother Matt hooked up with John Munson to form the Flops. As these side projects mounted, Semisonic went on indefinite hiatus in late 2001.