Chesney's career took off in 1991 when he starred in the film 'Buddy's Song' alongside Roger Daltrey & Michael Elphick. He played a young boy named Buddy Clark who claws his way up the treacherous ladder of the pop world with the help of Terry, his father, played by Roger Daltrey. Terry is a dodgy dealer who wants the best for his family but finds it hard to toe the line.

During the entire nineties, out of approximately 50,000 releases, only 13 of these spent more than 5 weeks at No.1. His song 'The One and Only' was in the top Twenty for the entire decade; it spent exactly 5 weeks at No.1, this made Chesney's record the twentieth most successful release of the entire decade.

Chesney is now working hard on several studio projectsincluding a new album, Another Fine Mess, which was supposed to be released in the summer of 2007.