Fretwell attended St. Augustine Webster Primary School in Scunthorpe and St. Bede's Catholic School in Ashby before furthering his study at John Leggott College. It was in his teenage years that he started his first band, named Label.
After moving to Salford in Fretwell, he started to earn notices in NME and Q. During this period songs such as "Emily" and "What's That You Say Little Girl?" were first written.
Fretwell decided to stay in Manchester permanently, later releasing 8 Songs which he released on Northern Ambition, a label owned by a friend. He left university after one year, and started to perform at local acoustic nights in the Manchester area. The first of these was at The Roadhouse, a venue in the centre of Manchester's Northern Quarter.
He later released the Something's Got to Give EP and The Lines, both self-financed. He then supported Travis, Elbow, Athlete, Keane and KT Tunstall. Signed to Fiction Records, and while under management by Colin Lester's and Ian McAndrew's Wildlife entertainment, his debut album Magpie, was released in November 2004. It was recorded at the Abbey Road Studios. It peaked at #27 in the UK Albums Chart in August 2005. The first single taken from the album was "Run" and was subsequently followed by "Emily" (2005) and the Four Letter Words EP. "Emily" reached #42 in the UK Singles Chart in August 2005. He had previously supported Oasis at Marlay Park in Dublin on 16 July 2005.
He was described by Q as "Scunthorpe's finest export... ever". Fretwell described this as flattering but not something he actively encouraged.
His version of Jeff Buckley's "Morning Theft" appeared on the 2005 tribute album Dream Brother: The Songs of Tim and Jeff Buckley.
His song "Bad Bad You, Bad Bad Me" was featured in an episode of the ABC family drama, Brothers & Sisters, called "The Missionary Imposition".
His most recent single was called "Scar", which was released on 3 September 2007. It was included on his album, Man On The Roof, which was recorded in New York, released on 10 September 2007, and featured James Iha.
Fretwell also played bass on tour with the Last Shadow Puppets, the side project of Arctic Monkeys' Alex Turner.
His song "Run" is the theme tune to the situation comedy, Gavin & Stacey and his song "Darling Don't" appeared on the third series of the teen drama Skins.
His song "Play" from the album Magpie was featured in the 2009 movie "The Joneses"
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