Despite some success with the single 'Cigarette Dangles' (the video appeared on Beavis and Butt-head), more label troubles ensued, and the band recorded their next two albums for the now-defunct Canadian label Iron Music. The band then went through difficulties with Chrysalis, and eventually followed Chrysalis president Mike Bone to Mercury Records in 1992, and released The Downward Road in 1993. Murumets left the band in 1992 in order to pursue the business side of music, and was replaced by Rachel Oldfield. Starting with the Spring 1990 tour for One Sided Story, Brad Barker (bass) and Susan Murumets (backing vocals) joined the lineup. Stanwyck and Sinclair left the band in early 1990, going on to form power pop band Universal Honey. The band's follow-up album with Rundgren, 1990's One Sided Story, featured the hit singles 'New Language' and 'Two Girls in One.' Although the album did not sell as well as Love Junk it was still a significant hit for the band. The album sold over 100,000 copies in Canada and was certified platinum. It was followed by 'She's So Young', which became their biggest hit single in Canada and also received radio play in the UK and became a minor hit there, and 'Hard To Laugh'. In January 1989 the song peaked at No.Р’В 6 on Billboard's alternative songs chart. 'I'm an Adult Now' was re-recorded and re-released as a single, making it to the charts a second time.

Their debut album, Love Junk, was produced by Todd Rundgren and released that year. In 1988, they signed to Chrysalis Records. The Amabile sisters left to concentrate on their own band, and were replaced by Kris Abbott (guitar and backing vocals) and Leslie Stanwyck (backing vocals) in early 1988. The band did not immediately sign to a record label, but instead released another independent single, 'Killed by Love', in 1988. The band signed with manager Jeff Rogers (Swell) in 1986. Their debut single, 'I'm an Adult Now', quickly became a smash hit across Canada in 1986, sparked by a low-budget video (made by Berg's director friend Nelu Ghiran) which made it onto the Canadian music video channel MuchMusic. They soon met bassist Johnny Sinclair and formed the band, adding sisters Tamara and Natasha Amabile as backing vocalists. Led by Edmonton, Alberta, singer and songwriter Moe Berg, The Pursuit of Happiness were launched in 1985 when he and drummer Dave Gilby moved to Toronto, Ontario. 4 Canadian Indies Hall of Fame, reunion shows, recent Canadian tour dates.

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