Glenn Peter Gregory was born on 16 May 1958 in Sheffield, England. His father, Howard, was a steel worker. As a teenager, he wanted to be an actor, but he worked in London as a photographer.[2]
Gregory knew the founding members of the Human League for many years. He had been singing and playing bass guitar in bands with Ian Craig Marsh since 1973, and was later also in a short-lived band with Martyn Ware.[4] In early 1981, he was contacted by Martyn Ware after the original incarnation of the Human League broke up, and was asked to join Heaven 17, a new band resulting from the break-up.[4]
The band Heaven 17 included the trio of Martyn Ware, Ian Craig Marsh, and Gregory as lead singer. The band released eight studio albums, and had many hits in the UK. However, by the late 1980s their popularity had declined. The band broke up in 1988, but reunited in 1996,[5] and played their first ever live concert in 1997. Marsh left the band in 2007, but Ware and Gregory continued to perform as Heaven 17.
In 1983, Gregory married singer Sarah Osborne of the Belgian pop group Allez Allez, but the two divorced after about three years. Gregory then married his second wife Lindsay who works for a design company. The couple have a son, Louis.[8][9]