They are best known for the UK number-one single "You're Not Alone".
Following Simply Red's 1991 album Stars, which garnered the band's greatest commercial success in the UK and worldwide at the time, Tim Kellett, last among its original lineup (as trumpet player), left the band. Meanwhile, Robin Taylor-Firth had just departed George Evelyn's techno/hip hop project Nightmares on Wax. The two met through a mutual friend who had recently joined Simply Red as bassist, and formed a musical collaboration (Taylor-Firth cites the disparity between his relatively "underground" work among Sheffield's electronic music and DJ community, and Kellett's mainstream history).
By 1994, three demos (which would become "Miracle", "Falling" and "You're Not Alone") were recorded in Kellett's cellar studio, upon which the two began their search for a singer. At this time, Kellett went on tour as keyboardist with Vini Reilly's The Durutti Column (which he played for a decade ago prior to joining Simply Red). While playing back pre-recorded keyboard samples on stage, Kellett heard a favourable vocal sample; the voice was that of Ruth-Ann Boyle, who had provided the samples for The Durutti Column's 1994 album Sex and Death.
Kellett contacted Boyle about singing for the collaboration; at the time working in a bar, and though disillusioned from past experiences singing in bands, Boyle accepted. After a "kind of an audition" with "Miracle", Boyle's membership in the band was set. The completion of the three initial demos attracted the interest of various UK record labels, and Olive signed with the top bidder, RCA, in September 1995.
The songwriting and recording process concluded with the completion of their first album in January 1996. The first single, "You're Not Alone," was released in 1996. Although the song took a year for audiences in England to catch onto, it eventually made number one in 1997, after the release of a new, remixed version, selling over 500000 copies. Popularity in America and Australia was muted, with the track falling short of an American Top 40 position and being restricted to a small musical niche with Australians. "Outlaw" followed not long after, with similar responses, as well as their first album, Extra Virgin in 1996.
Going along with the success of the remixed single, Extra Virgin was re-released with a bonus disc of remixes (by producers including Monkey Mafia, Roni Size, and the famed duo of Paul Oakenfold and Steve Osborne) in 1997.
The band went on tour to promote the album with a seven-piece band, playing three episodes of Top of the Pops ("You're Not Alone" twice in May 1997, "Outlaw" in August), a ten-date UK tour, as well as legs in Germany (alongside Faithless) and the U.S.
In the time leading up to the release of the follow-up album, Taylor-Firth had left the group to return to Nightmares on Wax, bringing it down to a duo. Meanwhile, they lost the support of RCA's UK branch, which dropped the band; however, they were then picked up by Madonna's Maverick Records (supposedly, with Madonna's personal approval after she attended one of their concerts in Germany).
In 2000, their presciently-named second album Trickle was released. While Trickle still displayed the distinctive Olive sound, the tunes were more dance-oriented. The best known song on this album was a cover of the 10cc song "I'm Not in Love"; it reached number one on the Billboard Hot Dance Music/Club Play chart, and was featured on the soundtrack to The Next Best Thing. Since then, like many trip-hop bands, little has been heard of them. The band has entered an extended hiatus. Kellett is focussing on songwriting for other artists so that he can spend more time with his family. Ruth-Ann joined Enigma as a vocalist, and released her first solo album 'What About Us' on June 4th 2007. It was released exclusively through iTunes.
At the 1997 Ivor Novello Awards (May 28, 1998), Kellett and Taylor-Firth received the Best Dance Music award for "You're Not Alone". The song was also covered as a 2002 single by German dance producer ATB.
During the American leg of the Trickle promotional tour, the band suggested that 60-70% of their audience demographic at the time was gay. This was recognized to the extent that the final show of the tour was played at the San Francisco Pride festival.