In 1959 Bailey became a photographic assistant at the John French studio, and in May 1960 he was a photographer for
John Cole's Studio Five, before being contracted as a fashion photographer for British
Vogue magazine later that year. He also undertook a large amount of freelance work. Along with
Terence Donovan and
Brian Duffy, Bailey captured and helped create the "
Swinging London" of the 1960s: a culture of fashion and celebrity chic. The three photographers socialised with actors, musicians and
royalty, and found themselves elevated to celebrity status. Together, they were the first real celebrity photographers, named by
Norman Parkinson "the Black Trinity". In 1966 Bailey directed the short film
G.G. Passion. The 1966 film
Blowup, directed by
Michelangelo Antonioni, depicts the life of a London fashion photographer played by
David Hemmings, whose character was inspired by Bailey. The Swinging London scene was aptly reflected in his
Box of Pin-Ups (1964): a box of poster-prints of 1960s celebrities including
Terence Stamp,
The Beatles,
Mick Jagger,
Jean Shrimpton,
P. J. Proby,
Cecil Beaton,
Rudolf Nureyev and
East End gangsters, the
Kray twins. The
Box was an unusual and unique commercial release. It reflected the changing status of the photographer that one could sell a collection of prints in this way. Strong objection to the presence of the Krays by fellow photographer,
Lord Snowdon, was the major reason no American edition of the
Box was released, and that a second British edition was not issued. The record sale for a copy of
Box of Pin-Ups is reported as "north of £20,000". At
Vogue, Bailey was shooting covers within months, and, at the height of his productivity, he shot 800 pages of
Vogue editorial in one year.
Penelope Tree, a former girlfriend, described him as "the king lion on the Savannah: incredibly attractive, with a dangerous vibe. He was the electricity, the brightest, most powerful, most talented, most energetic force at the magazine". Bailey also photographed album sleeve art for musicians including
The Rolling Stones and
Marianne Faithfull. Bailey directed and produced the TV documentaries
Beaton (1971) on
Cecil Beaton,
Visconti (1972) on
Luchino Visconti, and
Warhol (1973) on
Andy Warhol. In 1972, rock singer
Alice Cooper was photographed by Bailey for
Vogue magazine, almost naked apart from a snake. Cooper used Bailey the following year to shoot for the group's chart topping
Billion Dollar Babies album. The shoot included a baby wearing shocking eye makeup and, supposedly, one billion dollars in cash requiring the shoot to be under armed guard. In 1976, Bailey published
Ritz Newspaper together with David Litchfield. In 1985, Bailey was photographing stars at the
Live Aid concert at Wembley Stadium. As he recalled later: "The atmosphere on the day was great. At one point I got a tap on my shoulder and spun round. Suddenly there was a big tongue down my throat! It was
Freddie Mercury." In 1992, Bailey directed the BBC drama
Who Dealt? starring
Juliet Stevenson, story by Ring Lardner. In 1995 he directed and wrote the South Bank Film
The Lady is a Tramp featuring his wife Catherine Bailey. In 1998 he directed a documentary with Ginger Television Production,
Models Close Up, commissioned by Channel 4 Television. In 2012, the BBC made a film of the story of his 1962 New York photoshoot with
Jean Shrimpton, entitled ''
We'll Take Manhattan'', starring
Aneurin Barnard as Bailey. In October 2013, Bailey took part in Art Wars at the
Saatchi Gallery curated by
Ben Moore. The artist was issued with a stormtrooper helmet, which he transformed into a work of art. In October 2020 Bailey's memoir
Look Again (co-written with James Fox) was published by Macmillan Books, a review of his life and work. == Fashion ==