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 Brilleaux, 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.
Here's another biography written By Bert Muirhead
The following text is taken from Bert Muirhead’s book: “Stiff - The Story of a Record label”
All is re-published with kind permission by Bert Muirhead.
One of the originals of the Southend rock scene, Mickey started out in the Orioles in 1963 which, with lots of line-up changes, lasted until 1965 when he vanished from the Southend scene for some three years. He popped up again in 1968, during the 'blues boom' in Legend (he had apparently been in Bath during the missing years) who started off as a sort of country-blues band then moved into Orioles-style rock and roll before finally succumbing to the early 1970, heavy rock format. The famous Red Boot Album is the only record from this era worth looking out for and tracks from it and the album Moonshine make up the bulk of the songs on Legend (GET 2).
After the demise of Legend in 1972, Mickey took another holiday from playing before returning to the fray with the Mickey Jupp Band in 1975, a ten-piece outfit who played a fine blend of R and B, rock 'n' roll, Jupp originals and pop hits. The budding generation of Southend rockers (Kursaal Flyers, Dr Feelgood etc) all mentioned Mickey's name as the main man on the scene. He was briefly signed to Arista before moving to Stiff, but left very quickly after the Train tour and the Juppanese album, returning briefly in a one-off deal in 1981. He has since recorded albums for Chrysalis and more recently A & M (Some People Can't Dance) and nearly had a hit when Joggin' was adopted as the theme tune for the London marathon.