Oldham's father, Andrew Loog, was a United States Army Air Forces lieutenant, a Texan of Dutch descent, who served with the Eighth Air Force. Loog was killed in June 1943 when his B-17 bomber was shot down over the English Channel: he was buried at the Ardennes American Cemetery and Memorial in Belgium. Oldham's Australian mother, Celia Oldham, was a nurse and comptometer operator. He attended the Aylesbury School for Boys, Cokethorpe School in Oxfordshire, St Marylebone Grammar School and Wellingborough School in Northamptonshire.
A self-proclaimed hustler who spent teenage summers swindling tourists in French towns, Oldham's interest in the pop culture of the 1960s and the Soho coffeehouse scene led to working for Carnaby Street mod designer John Stephen and later as an assistant to then-emerging fashion designer Mary Quant. Oldham became a publicist for British and American musicians and for producer Joe Meek. Among his projects were stints publicizing Bob Dylan on his first UK visit and the Beatles for Brian Epstein in early 1963.
In April 1963, a journalist friend recommended that Oldham see a young R&B band called the Rolling Stones. Oldham saw potential in the group being positioned as an "anti-Beatles" - a rougher group compared to the "cuddly moptop" image of the Beatles at that time. Oldham, still a teenager, rapidly acquired a seasoned business partner (Eric Easton) and took over management of the Stones who had been informally represented by Giorgio Gomelsky. Oldham had previously been business partners with Peter Meaden, first manager of the Who, but they had fallen out. Oldham signed recording rights to the Stones to Decca, targeting A&R head Dick Rowe, who had earlier declined to sign the Beatles.
Among strategies devised and executed by Oldham to propel the group to success:reassigning Ian Stewart from onstage keyboard player in May 1963 to studio-only play. This was to keep their public appearance as a five-man group of slender young men; Oldham said that six was too many and Stewart was five years older (although Bill Wyman is older). Stewart stayed on as the road manager and continued to contribute keyboard parts to the band's recordings and live performances, and remained an influence.
bringing John Lennon and Paul McCartney to the recording studio, which led to their song "I Wanna Be Your Man" becoming the Rolling Stones' second single;
encouraging Mick Jagger and Keith Richards to start writing their own songs ("Tell Me" was their first); and
promoting a "bad boy" image for the Rolling Stones in contrast to the Beatles. Oldham generated widely reprinted headlines like "Would You Let Your Sister Go with a Rolling Stone?" and provocative album-cover notes such as a satirical incitement to fans to mug a blind beggar for funds to buy the album.
Oldham and Eric Easton negotiated a recording contract which was very favourable to themselves. Instead of having the Stones sign directly with Decca they set up a company, Impact Sound, which retained ownership of the group's master tapes, which were then leased to Decca—an idea learned from Phil Spector. Impact Sound received a 14% royalty from Decca but only paid 6% to the Stones, out of which Oldham and Eric Easton received a 25% management fee.
Oldham produced all Rolling Stones recordings from 1963 until late 1967 despite having no previous experience as a producer. According to the Rolling Stones' website "Accounts regarding the value of his musical input to the Stones recordings vary, from negligible to absolute zero". Though lacking technical expertise in the studio, it is thought that Oldham was good at seeing the "big picture" of the Rolling Stones' image and sound. He discovered Marianne Faithfull at a party, giving her Jagger and Richards' "As Tears Go By" to record. He also developed other studio talent with his Andrew Oldham Orchestra, in which Rolling Stones as well as London session players (including Steve Marriott on harmonica) recorded pop covers and instrumentals. As his success increased, Oldham thrived on a reputation as a garrulous, androgynous gangster who wore makeup and sunglasses and relied on his bodyguard "Reg" to threaten rivals.
During this period, Oldham took advertising space in the Melody Maker to unfavourably compare Cilla Black's version of "You've Lost That Lovin' Feelin'" with the competing original by The Righteous Brothers.
In 1965 Oldham hired Allen Klein as his business manager. On Oldham's behalf Klein renegotiated the Rolling Stones' contract with Decca, excluding Oldham's partner, Eric Easton. But over the next two years Oldham's relations with the Stones were strained by his drug use and inattention to the group's needs. When Jagger and Richards were arrested for drug possession in 1967, instead of devising a strategy for their legal defence and public relations, Oldham fled to the United States, leaving Klein to deal with the problem. Oldham was forced to resign as manager of the Rolling Stones in late 1967 and sold his rights to the group's music to Allen Klein the following year.
In 1965, Oldham set up Immediate Records, among the first independent labels in the UK. Among the artists that he signed and/or produced or guided were PP Arnold, Chris Farlowe, the Small Faces, John Mayall & the Bluesbreakers, Rod Stewart, the Nice, Jimmy Page, Jeff Beck, Eric Clapton, Amen Corner, the McCoys, the Strangeloves, Humble Pie and Duncan Browne.
With Arthur Greenslade he was credited as the co-writer of "Headlines", the B-side of "Ride on Baby" (IM 038), by Chris Farlowe, which was released in October 1966.
Oldham also helped Derek Taylor publicise the Beach Boys' Pet Sounds (1966) album by publishing advertisements praising the album. He enlisted songwriter Billy Nicholls to record a British response, the album Would You Believe? (1968). After the Small Faces disbanded in 1969, he put together Humble Pie, featuring Steve Marriott (formerly of the Small Faces) and Peter Frampton (formerly of the Herd).
In the 1970s and 1980s, Oldham worked primarily in the United States. He produced Donovan, Gene Pitney and other artists. In the mid-1980s, he made Colombia his primary residence after marrying Esther Farfan, a Colombian model. There he became a mentor for local bands.
A recording by the Andrew Oldham Orchestra was rediscovered in the 1990s when the Verve used a string loop based on the orchestral arrangement of the Rolling Stones song "The Last Time" in their song "Bitter Sweet Symphony"; in the ensuing court battle, songwriting royalties for the Verve track were awarded to Allen Klein's ABKCO Records, the owner of the copyright for "The Last Time".
Oldham co-wrote a biography of ABBA in the 1990s and three autobiographies: Stoned (1998), 2Stoned (2001), and Rolling Stoned (2011) in which he and other music figures recount his days as a manager, producer and impresario. He was inducted into Rock and Roll Hall of Fame in 2014.
In 2005, Oldham thanked the drug rehab organisation Narconon for saving his life from his cocaine addiction. That same year, he was recruited by Steven Van Zandt to host a radio show on Van Zandt's Underground Garage radio channel heard in North America on Sirius Satellite Radio. Oldham has a three-hour show on weekdays and a four-hour weekend show. Since 2006, he has worked with the Argentine musician Charly García. In 2008, he worked on the production of Los Ratones Paranoicos' new album. In 2008, he produced and arranged Canadian singer Wyckham Porteous's album 3 A.M. and has been managing and working with the Colombian rock artist Juan Galeano.
In 2014, Oldham overheard Canadian artist Ché Aimee Dorval singing backup on a friend's track he was helping to produce, and he subsequently signed her to his label. In September 2014, Oldhams's label released Dorval's second studio EP, Volume One. She was also given two covers to sing on his recently released (2013) album consisting of Rolling Stones' songs entitled Andrew Oldham Orchestra and Friends play the Rolling Stones Songbook Vol. 1. Dorval sang "As Tears Go By" and "Under My Thumb".
The song "Andrew's Blues", sung by the Rolling Stones and appearing on the Black Box collection CD1, is a humorous if scathing evocation of Oldham.