Trip Shakespeare was an American rock band formed in Minneapolis, Minnesota and active from the mid-1980s to early-1990s. The band included Dan Wilson and John Munson, who would later go on to be founding members of Semisonic.

The band originated when Harvard University English student Matt Wilson (guitar/vocals) teamed up with Elaine Harris (drums), a Harvard grad student in biological anthropology, in the early 1980s. Harris had responded to a notice posted by Wilson seeking "wicked percussion hands."

Matt Wilson and Munson had played together in an earlier band (E Brown), and Wilson had not been impressed by his bass playing, so he didn't want Munson to audition for the new band. "But he came over anyway and played, and he'd improved a lot," Wilson later recalled. "We ended up begging him to just give it a try and stay around."

In 1986 drummer Tim Rowe, who had played with Munson in several other bands, joined the group as percussionist. They performed as a quartet for several months before Rowe left the band during the recording of Applehead Man to join The Nietzsches with the former guitarist for E. Brown, Jimmy Harry.

Matt Wilson originally proposed that the band be named Kirk Shakespeare, after two of his heroes: James T. Kirk and William Shakespeare. "I think maybe John and Elaine didn't want to be in a band named after Matt's two heroes, so they changed Kirk to Trip," explained Dan Wilson, Matt's older brother, who joined the band later. In an interview with the Chicago Reader's Bill Wyman, Matt Wilson suggested that Dan was convinced to join by the quality and potential suggested by Applehead Man: "We sent him the first record almost as a demo tape, to get him to join up, and kept telling him how serious we were."

In 1986, the trio self-released their debut album. "The first album, Applehead Man, we just put all the songs we knew on there," Matt Wilson later said. One of these was the title track, which described a head being carved from "the brightest fruit...furthest from the road on the apple farm."

With its lineup complete, the band released a follow-up album, Are You Shakespearienced?, on the Minneapolis-based independent label Gark Records in 1988. Recorded live in the studio without headsets, the album featured "Toolmaster of Brainerd," a song that "insanely links dairyland folklore with the enduring rock myth of guitar-hero supremacy." Hailing from "Brainerd where the children go to milking school," the Toolmaster

"Toolmaster," according to the Twin Cities alternative new weekly paper City Pages, "perfectly captured the tension between Minneapolis ambition and outstate resignation that pretty much informs life in the Land of 10,000 Lakes."