Jupp began his career with the Essex-based British R&B group the Orioles in the early '60s. The band earned a devoted local following in the early '60s, yet they never had the opportunity to record. The Orioles broke up late in 1965 after Jupp was arrested for not making alimony payments to his wife. Three years later, he returned to music, forming Legend, who laid the groundwork for English pub rock of the early '70s. Following the release of their third album in 1971, Legend disbanded and Jupp took another lengthy break from music. When he was coaxed back into performing in 1975 by Lee Brileaux, the lead singer of Dr. Feelgood, pub rock was in its last days yet Jupp was well respected in the scene, since both Ducks Deluxe and Dr. Feelgood had recorded versions of his songs ("Cheque Book" and "Down at the Doctors," respectively).

Jupp released his first solo single, "Nature's Radio," on Arista Records in 1978. The single led to a contract with Stiff Records, who released the "Old Rock 'N' Roller" single and the Juppanese album in 1978; the bulk of Juppanese was recorded with Rockpile and produced by Nick Lowe. Released the same year as his debut, Mickey Jupp's Legend featured material from his previous band. Following the release of Juppanese, Jupp joined Stiff's Rail Tour, although he left the lineup before it hit the U.S. because he was afraid of flying. Shortly afterward, he left Stiff Records and signed with Chrysalis in 1979. The same year he released Long Distance Romancer, which was produced by 10cc members Kevin Godley and Lol Creme; like Juppanese, it failed to gain a large audience. Jupp moved over to A&M Records in 1982, releasing Some People Can't Dance. After releasing one more record on A&M, 1983's Shampoo Haircut and Shave, he was dropped from the label. Jupp spent the rest of the '80s and '90s touring the U.K., releasing the occasional album on independent labels.