Hawkes' 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. Written By Nik Kershaw, the song was later featured in the opening credits of Doc Hollywood (1991), starring Michael J. Fox; in the 2009 movie Moon, as the song Sam Rockwell wakes up to every morning; and again in the 2011 film Source Code (also directed by Moon director Duncan Jones) as the cell phone ringtone of Michelle Monaghan's character. The single spent five weeks at number one. He has released eight singles including "I'm a Man Not a Boy" and "Another Fine Mess".
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.
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; it was his biggest-selling single for over a decade. The following album of the same title featured fifteen songs written by Hawkes.
Hawkes was involved in a project called the Lexus Symphony Orchestra, a corporate promotion designed to showcase the quality of Lexus' in-car audio systems. Hawkes composed two original pieces of music performed by the London Symphony Orchestra for these events held at Castle Howard and Crystal Palace, in August 2007.Hawkes was confirmed to appear in new musical, Can't Smile Without You (featuring songs of Barry Manilow). In the show, Hawkes plays the part of Tony Lowiman who falls in love with a girl called Mandy when he visits New York. Things take a turn for the worse when Tony is brutally attacked one night outside a club. 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.
Hawkes appeared briefly in a cherry picker on Celebrity Big Brother (shown on 8 January 2009) on Channel Four. "The One and Only" was used as a cue to have contestants worship at a Chesney Hawkes shrine. While other contestants were required to be paparazzi who had to take photos of any celebrities that appear in the cherry picker which was raised above the house compound wall.
Entrepreneur Duncan Bannatyne is a fan and Hawkes performed as a surprise at his birthday party.
In January 2011, Hawkes performed at the live finale of Louie Spence's Showbusiness, which will be broadcast at the end of the current series.
During February and March 2011, he took part in the BBC series Let's Dance For Comic Relief.
Chesney now performs a mixture of his own material and covers at University Freshers week. He still receives the best applause for "the one and only".
In May 2011, Hawkes took part in the ITV series Sing If You Can.
In September 2011 Chesney appeared as Joseph in Milton Morrissey's new production of Joseph and his Amazing Technicolor Dreamcoat, premiering in Guernsey. The production team included James Milton, Paul Morrissey, Andy Smith and Nick Winston and gained critical acclaim locally.
