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Born and raised in London, Fielding was educated at Croydon School of Art and Buckinghamshire Chilterns University College (now Buckinghamshire New University).
During the late 1990s he became a stand-up comedian, through which he met Barratt, with whom he established the Mighty Boosh.
Fielding also made a short appearance in the film Plunkett & Macleane as a bystander to Robert Carlyle's scuffle in a brothel.The show generated a cult fan following and won a variety of awards.During the 2000s, he also had smaller roles in a number of comedy shows for Channel 4 including Nathan Barley, The IT Crowd, AD/BC: A Rock Opera and Garth Marenghi's Darkplace.Fielding appeared on The Charlotte Church Show as a special guest.
At Bill Bailey's request, Fielding stood in as a team captain for three episodes during Season 21 of Never Mind the Buzzcocks.In 2008, Fielding appeared with comic partner Julian Barratt on Transmission.As usual, he wore a somewhat flamboyant attire, this time featuring Cuban heels and polka dot trousers.His highly animated stand-up routine included surreal stories, physical comedy, characters, and songs, much like his later work in The Mighty Boosh.