At only 17, Jobson first gained success as front-man with the Scottish punk band, The Skids, who had a string of hits in a 2-year period, from 1979 to 1981, the biggest song being the top-10 hit, "Into the Valley" in 1979. The band was formed by Jobson and his friend, Stuart Adamson, who later formed the band, Big Country. After Adamson departed the band, The Skids commercially declined and disbanded in 1982. Shortly after, Jobson formed the short-lived band, The Armoury Show and, although not a commercial success, were critically-acclaimed by the music press. This was to be Jobson's last foray as a musician as he turned his attention to modeling for a few years and once claimed he was the highest male earner in the industry.

For the past decade, Jobson has been working on SKY-TV in Britain, presenting predominately film shows and the odd music show on VH-1 Britain. However, after the death of his old friend, Stuart Adamson, in December 2001, he reunited The Skids at a tribute gig for Adamson on May 31, 2002 in Glasgow and, needless to say, stole the show. His next project will be in directing films - he is currently working on his first film in this category, 16 Years of Alcohol (2003).