While such diversity earned him critical praise and a cult following, it didn't result in widespread acclaim until 1982's Night and Day, which launched the jazzy hits "Steppin' Out" and "Always Something Breaking Us In Two." Once he had a taste of success, Jackson didn't become more accessible -- he became weirder, crafting a number of self-consciously difficult records intended to push the boundaries of pop. Following his 1987 classical album Will Power, Jackson's audience began to decline, and by the early '90s, his cult was a fraction of its size a decade earlier. Despite his shrinking audience, Jackson was even less compromising in the '90s than he was in the '80s, eventually abandoning pop altogether. Jackson began playing music as child, learning violin at the age of 11 and convincing his parents to invest in a piano by the time he was a teenager. He began writing songs as an adolescent, and he studied percussion and oboe in school as well.
Following high school, he received a scholarship for London's Royal Academy of Music, and he studied composition at the institution between 1971 and 1974. Following his graduation, he performed with a band named Arms and Legs, and was then hired as the musical director for the Portsmouth Playboy Club. Within a few years, he recorded a demo album of original songs that landed him a publishing deal with Albion Music. By 1978, he had secured a record contract with A&M. Released in early 1979, at the height of new wave, Jackson's debut album Look Sharp! was a collection of nervy, edgy pop songs recorded in just a week and a half. Highlighted by the Top 25 single "Is She Really Going Out With Him?," Look Sharp! was widely praised and became a Top 20 hit in the U.K. Jackson followed it six months later with I'm the Man, a record that closely resembled the debut. Not wanting to be pigeonholed as an Elvis Costello-style pop songwriter, Jackson took a detour on his next record, 1980's Beat Crazy, recording a full-fledged reggae and ska album. The album received mixed reviews and weak sales, but it played well with his cult audience. Jackson followed the reggae experiments of Beat Crazy in 1981 with Jumpin' Jive, a collection of swing and jump blues. He supported the album with a tour featuring a big band, and the record became a cult hit.
Following Jumpin' Jive, Jackson moved to New York, where he attempted to write a jazzy, sophisticated pop album in the vein of Cole Porter. The resulting album, Night and Day, was widely praised upon its 1982 release, and the album proved to be his commercial breakthrough, as "Steppin' Out" reached the U.S. Top Ten and the ballad "Always Something Breaking Us In Two" also became a hit. Jackson delved further into jazz with the record's follow-up, Body and Soul. Boasting a cover modeled on a Coleman Hawkins sleeve, Body and Soul was even jazzier than its predecessor, and it produced the Top 20 hit "You Can't Get What You Want (Til You Know What You Want)." Breaking away from his sophisticated pop leanings, Jackson conceived his next record as a live album of entirely new material, recorded directly to two-track, and performed in front of a live audience who would not be audible on the recording. The album was also conceived as one seamless piece, designed for a compact disc -- it was released as a double album on vinyl, but one side was blank. The resulting record, 1986's Big World, received decidedly mixed reviews and was a only a moderate hit.
The artistic contrivance of Big World was only the beginning of Jackson's wild deviations from the norm. He had already proven himself an idiosyncratic musician, yet few observers would have predicted that his next album would be a full-fledged symphony. Will Power was poorly received upon its 1987 release, and Jackson, who was contemptuous of the bad reviews, nevertheless backed away from its complexities on his next album. Following the double-disc set Live 1980/86 in 1988, Jackson released Blaze of Glory, a collection of pop songs designed to tell a semi-autobiographical story, in 1989. Blaze of Glory was moderate hit, producing the album-rock hits "Down to London" and the title track. It was also his last album for A&M -- he signed to Virgin for 1991's straight-ahead pop/rock record, Laughter & Lust. Despite strong reviews, Laughter & Lust wasn't the hit it was designed to be, and Jackson abandoned pop music once and for all with 1994's Night Music, a fusion of classical music and show tunes that was greeted with mixed reviews and poor sales. Heaven and Hell followed in 1997, and in the spring of 2000 Jackson resurfaced with Summer in the City--Live in New York. Night and Day II, featuring guest spots from Marianne Faithfull, Dave DeVere, and Sussan Deyhim, followed later that fall. ~ Stephen Thomas Erlewine, All Music Guide