During the '80s, Aimee Mann led the post- ew wave pop group $'Til Tuesday. After releasing three albums with the group, she broke up the band and embarked on a solo career. Her first solo album, Whatever, was a more introspective, folk-tinged effort than $'Til Tuesday's albums, and received uniformly positive reviews upon its release in the summer of 1993. However, the album was only a small hit, spending only seven weeks on the American charts, where it peaked at 127. Nevertheless, Whatever rejuvenated her career -- after its release, critics were praising her songwriting, as were peers like Elvis Costello, Difford & Tilbrook, and Andy Partridge.

Early in 1995, Mann had a modest hit with "That's Just What You Are," a song included on the soundtrack to the television series Melrose Place. Following the success of the single, Mann was set to release her second solo album in the spring of 1995, but her record label, Imago, filed for bankruptcy before its release. She signed a contract with Reprise Records after Imago went under, but Imago prevented her from releasing any records. For most of 1995, Mann battled Imago in an attempt to free herself from the label, eventually winning her independence at the end of the year. After her dispute with Imago was settled, she signed with DGC Records. Mann's second album, I'm with Stupid, was released in England in the late fall of 1995 and in January of 1996 in America. Again, it was greeted with positive reviews yet weak sales.