Damon Gough chose his stage name from the title character in the show Sam and his Magic Ball, which he saw on television at a party in Trafford, Greater Manchester in 1995.

Before he thought of using this name he made some business cards, each one unique, with a printed picture of a drawing by his nephew, and a small collage by Gough. This was then laminated and given out to friends and people at clubs in Blackburn and Manchester.

A chance meeting with Andy Votel at the Generation X bar in Manchester, where Gough's friends Scott Abraham and Damon Hayhurst were contributing to an exhibition by the Space Monkey Clothing Company and Votel was DJing, led to the foundation of Twisted Nerve Records. Badly Drawn Boy's first seven-inch single, EP1, was pressed the following year to critical acclaim, although only 500 copies were made.

In 2002, Q magazine named Badly Drawn Boy in its list of the "50 Bands To See Before You Die", although this was as part of a sub-list of "5 Bands That Could Go Either Way" on account of Gough's tendency to talk and tell stories for extended periods rather than playing songs.

Gough's recording career began in September 1997 with the five track vinyl release "EP1". This was distributed among friends and family members. With only 500 being pressed, the record is now considered something of a Holy grail for Badly Drawn Boy enthusiasts, with copies commanding up to £100 on eBay.

In April 1998, Gough released his second EP, "EP2". This featured one track less than its predecessor but twice as many copies were pressed. The highlight track "I Love You All" was later transferred to a music box which was released alongside the EP. The box plays eleven seconds of the song and is considered much rarer than the record itself due to its limited production.

Gough’s third EP, "EP3", was released in November 1998 on both CD and vinyl formats, and was the first release in what would become a long-term partnership with XL Recordings. "Road Movie" was released as a live recording with Gough's fellow Mancunian band Doves. The B-side to the single was another track from the EP, "My Friend Cubilas". Videos were recorded for both tracks.

It Came from the Ground was the next EP, released in March 1999 on CD and vinyl. The style of this recording focused on woodland environments, an aspect displayed in both the cover art and the title track's video. Also released during this period was the single "Whirlpool". An instrumental was released on vinyl in April 1999.

Gough's last EP, Once Around the Block was released in August 1999 in two vinyl formats and one CD edition. The release is almost short enough to be considered a single.