Failing to graduate from the college in 1928, he took up art classes at the Regent Street Polytechnic. It was around this time that he changed his name to Quentin Crisp.
Simultaneously, he started visiting cafes of Soho, taking his effeminate behaviour to another level by experimenting with make-up and women's clothes. He even started interacting with other homosexual men and rent boys and worked as a male prostitute.
Leaving home in 1930, he moved to the centre of London. It was while at London that he enhanced his effeminate behaviour and appearance by wearing loud make-up, long and painted finger nails and crimson red hair.
While his bizarre and eccentric appearance amused some Londoners, for most others it was outrageously weird and attracted hostility and violence.
During World War II, he enlisted himself in the army but was rejected on ground of his personality and changing sexual perversion.
In 1940, he relocated his lodging to a bed-sitting room in 129 Beaufort Street, which eventually served as his residence for the next four decades.
In 1941, he let go of his job as an engineer's tracer to take up modelling in life classes in London and Home Counties. For the next three decades, he continued posing and posturing for artists
At the time of penning what eventually became known as 'The Naked Civil Servant', he had already published three short books. 'The Naked Civil Servant' was earlier named 'I Reign in Hell' but was changed on Caroll's insistence.
Published in 1968, the book gave a detailed account of his work and life in a homophobic British society. It generally garnered positive reviews from its readers.
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It was after the success of the book that he was asked by Denis Mitchell to talk about his life in a short documentary made by the latter. The discussion brought him immense limelight and fame and so did to his book.
No sooner than in 1975 he was asked to star in the television drama serial which was to be based on his book, 'The Naked Civil Servant'. With the same name, the series had him star alongside John Hurt. It was broadcast on both US and British television.
The success of the tele-series helped him think of his career as a performer and lecturer. Subsequently, he devised his own one-man show. While the first half of the show included entertaining and humorous monologue, the second part included an interactive session with a question-and-answer round with the audience.
In 1975, his autobiographical book, 'The Naked Civil Servant' was re-printed. His own-man show was a runaway success and gave him a complete makeover in the social circles who thought of him as a narrator and a witty speaker.
In 1976, he made his film debut with the Royal College of Art's low-budget produced movie, 'Hamlet'. A 65 minute adaptation of the Shakespearean play, he played the role of Polonius, supported by Helen Mirren, who portrayed the characters of Ophelia and Gertrude.
In 1978, his show was a sold out at the Duke of York's Theatre in London. Following the success of his show in London, he took the show to New York. Despite certain hitches during his stay in New York, he decided to relocate permanently to the country.
As such, in 1981, he moved to America with a few possessions. He eventually found a place to stay in the small apartment on East 3rd Street in Manhattan's East Village. Post relocation, he enlisted his number in the telephone directory first thing.
He was largely open to strangers to the point of gaining dinner invitations from anyone whether known or unknown. While the inviter would pay for his dinner, he entertained the latter with his jokes, humorous tales and creative stories during and after the meal. Thus, these dinners turned out to be one-of-the-kind shows.
Over the years, he continued to write his books on the importance of contemporary mannerism as a means of social inclusivity. He accepted invites to social parties and functions, wrote movie reviews and columns for US and UK magazine and newspapers
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Other than his books and show, he acted in several television and films. In 1985, he starred in the film, 'The Bride'. In the movie, Sting played the central character of Baron Frankestein.
While in 1987 he appeared in the episode 'First Light' on the television show, 'The Equalizer' in 1988, he was cast as the narrator of Richard Kwietniowski's short film 'Ballad of Reading Gaol'. The film was based on the Oscar Wilde's poem.
The decade of 1990s proved to be a quintessential phase in his career. He bagged a lead role in the 1992 low-budget independent film, 'Topsy and Bunker: The Cat Killers'. His character was that of a doorman of a flea bag hotel in a shabby and dilapidated neighbourhood.
The same year, he played the role of Elizabeth I in the film Orlando. Though the role-play was a tough job, he excelled in his portrayal and won much acclaim and appreciation for his touching performance.
Some of the other films that he was a part of include, 'Philadelphia' and 'To Wong Foo Thanks For Everything, Julie Newmar'. 'American Mod' was his last independent movie, while 'HomoHeights' was his last feature film.
In 1995, he was interviewed by The Celluloid Closet, which highlighted how Hollywood films depicted homosexuality. The same year, he brought out his third volume of the memoirs titled, 'Resident Alien'.
In June 1995, he served as one of the guest entertainers at the second Pride Scotland festival in Glasglow. Three and a half years later, in December 1998, he celebrated his ninetieth birthday by performing at the opening night of his one-man show, An Evening with Quentin Crisp, at The Intar Theatre on Forty-Second Street in New York City.