Hawkes's career began at 19, when he appeared as the title character in the film Buddy's Song. In March 1991, he released his biggest single "The One and Only" from the film's soundtrack, on which his younger brother, Jodie, was the drummer. Written by Nik Kershaw, the song was later featured in the opening credits of Doc Hollywood (1991), starring Michael J. Fox.

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Hawkes was born in Windsor, Berkshire. He was named after the singer and comedian Chesney Allen. His father is the singer Len 'Chip' Hawkes, formerly with the 1960s band The Tremeloes.

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He has released eight singles including "I'm a Man Not a Boy" and "Another Fine Mess".

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In 1993, his single "What's Wrong With This Picture?" reached number 63 in the UK, and his 2002 collaboration with Adam Schlesinger of Fountains of Wayne, "Stay Away Baby Jane", reached number 74 in the UK Singles Chart.

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Hawkes returned to the media's attention with his involvement in Channel 4's The Games in March 2005, in which he won a Bronze Medal. He also took part in the ITV programme Hit Me Baby One More Time in April that year. He released a single called "Another Fine Mess" in May 2005, it reached number 48. The following album of the same title featured fifteen songs written by Hawkes.

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Hawkes appeared in a musical, Can't Smile Without You (featuring songs of Barry Manilow). In the show, Hawkes plays the part of Tony Lowiman. The musical includes over 40 Barry Manilow songs. National tour started at the Liverpool Empire Theatre on 15 September 2008, prior to performances in the West End.

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In 2015, Hawkes competed in Celebrity MasterChef on BBC One. 

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To this day Chesney is still writing, recording and touring the UK and beyond.