In 1967, O'Sullivan moved from Swindon to
London in pursuit of a career in music. Determined to get a record deal and looking to stand out, he created an eye-catching visual image consisting of a
bowl cut, cloth cap and short trousers. O'Sullivan said his love of
silent film inspired the look. He obtained a five-year contract with April Music,
CBS Records' house publishing company, after coming to the attention of the professional manager, Stephen Shane, who also suggested changing his name from Ray to Gilbert as a play on the name of the light opera partnership of
Gilbert and Sullivan. He was paid an advance of £12 (), with which he bought a piano. He was signed to CBS Records by the
A&R manager Mike Smith, who produced
the Tremeloes,
the Marmalade and
the Love Affair. O'Sullivan's first single was "Disappear", produced by Smith and released in November 1967, credited to the mononym "Gilbert". It failed to chart, as did his second single, "What Can I Do", released in April 1968. A switch to the Irish record label
Major Minor Records, in 1969, yielded a third single, "Mr. Moody's Garden", which was again unsuccessful. O'Sullivan then sent some demo tapes to
Gordon Mills, the manager of
Tom Jones and
Engelbert Humperdinck, whereupon O'Sullivan was signed to Mills' newly founded label, MAM Records. Mills did not agree with O'Sullivan's self-created image, but O'Sullivan initially insisted on using it. O'Sullivan's signature look garnered much attention and often saw him compared to the
Bisto Kids. O'Sullivan explained his thinking behind his appearance in a 1971 interview: "My mother probably doesn't like
Neil Young because she hates the way he looks, his hair and everything. If you can get them interested in the way you look then they tend to like the music. The thing which I'm trying to create is of the thirties;
Keaton and
Chaplin."
Early success At the end of 1970, O'Sullivan achieved his first UK
top 10 hit with "
Nothing Rhymed", where it earned O'Sullivan his first
gold disc. O'Sullivan released his debut album,
Himself, in August 1971. O'Sullivan opted not to tour in promotion of the album, but did however make a number of appearances on British television during 1971, most notably recording an edition of the
BBC's
In Concert broadcast on 18 December 1971. In 1972, O'Sullivan achieved international fame with "
Alone Again (Naturally)", a
ballad which touches on
suicide and loss. The single peaked at no. 3 in the UK but in America spent six non-consecutive weeks at number one on
Billboards Hot 100, selling nearly two million copies. It peaked at no. 2 in New Zealand (during an 11-week chart run) and spent two weeks at number one in Canada (13 weeks in the Top 40); and reached number one in Japan (during a 21-week chart run). In America the single ranked no. 2 (behind
Roberta Flack's "
The First Time Ever I Saw Your Face") in
Billboards year-end chart, based on both sales and airplay. In 1973, both titles were
Grammy-nominated for both
Song of the Year and
Record of the Year, with Flack winning in both categories. This international success coincided with a new image, with O'Sullivan discarding the appearance he had used since 1967. He unveiled a more modern 'college-like' look in which he often wore a
sweater bearing a large letter 'G'. O'Sullivan followed up on the success of "Alone Again (Naturally)" with "
Clair", which reached no. 2 in the United States on the Hot 100 and no. 1 in the UK, Norway, France, Belgium, Ireland and Canada (14 weeks in the Canadian Top 40). Its parent album (and O'Sullivan's second),
Back to Front, spawned a further hit with "
Out of the Question", which reached no. 17 in the US and no. 14 in Canada. and in May 1973 he won an
Ivor Novello award for "British Songwriter of the Year". In 1973, O'Sullivan released his third album, ''
I'm a Writer, Not a Fighter'', which reflected a new emphasis on
rock music and
funk influences. Its lead single, the
electric keyboard-based "
Get Down", reached number one in the UK, Belgium and Germany, no. 7 in both the US and Canada, and no. 3 in the Netherlands. By 1974, his sales were decreasing. It was O'Sullivan's first single since his 1970 breakthrough to miss the top 40 of the
UK singles chart, reaching a peak of no. 42. His November 1974 single "Christmas Song" reached no. 12 in the UK and no. 5 in Ireland. In June 1975, O'Sullivan had his last top 20 hit, "I Don't Love You But I Think I Like You". in which he sued
rapper Biz Markie over the rights to use a
sample of his song "Alone Again (Naturally)". O'Sullivan has continued to record and perform into the 21st century. He enjoys
particular acclaim in Japan. O'Sullivan, feeling embarrassed, wrote a "long apologetic" letter to
Michael Eavis, yet received no response; O'Sullivan was never asked to return to the Glastonbury stage, which led to a brief period of sourness between him and his agent. O'Sullivan played London's
Royal Albert Hall on 26 October 2009. On 26 August 2010, O'Sullivan joined Hypertension, a record company whose artists have included
Leo Sayer,
Chris de Burgh,
Fleetwood Mac, and
Gerry Rafferty. O'Sullivan's album
Gilbertville was released on 31 January 2011; it featured "All They Wanted to Say", which dealt with the 2001
attacks on the World Trade Center, and his single "Where Would We Be (Without Tea)?". On 19 July 2011, O'Sullivan played live on the
BBC Radio 2 Ken Bruce Show. On 26 August that year, the documentary
Out on His Own was broadcast by
BBC Four (before by Irish
RTÉ). In March 2012, the compilation album ''Gilbert O'Sullivan: The Very Best Of – A Singer & His Songs'' entered the UK Albums Chart at No. 12. 2015 saw O'Sullivan re-emerge on Irish and BBC radio and television. He toured Ireland beginning of June and on 8 June 2015 his album
Latin à la G! was released. On 24 August 2018, O'Sullivan released his 19th studio album, ''Gilbert O'Sullivan''. The album entered the
UK Albums Chart at No. 20, his first UK charting studio album in over 40 years. He received the honor in person on 27 March 2024. ==Personal life==