Influenced by Simon & Garfunkel, Bob Dylan, and the Clash, Bragg began his musical career in 1977 by forming the punk rock band Riff Raff and later launching a solo career under the name Spy Vs. Spy which led to a 1983 release, and included his iconic "A New England," a Top 10 hit in the UK for Kirsty MacColl later that year.
This was followed by releases under his own name including Between the Wars, Talking with the Taxman about Poetry, Workers Playtime, Don't Try This at Home, and The Internationale, which included the song, "I Dreamed I Saw Phil Ochs Last Night."
In 1998, a collaboration with the band Wilco and Natalie Merchant celebrating the work of Woody Guthrie produced the first of three Mermaid Avenue albums, with the first nominated for a Grammy in the Best Contemporary Folk Album category.
A developing interest in English national identity informed his 2002 album England, Half English and a move closer to English folk music roots with The Imagined Village, who recorded an album of updated versions of traditional English songs.
For the entirety of Bragg's 30-year-plus recording career he has been involved with grassroots political movements. In addition to being a published writer, playwright, and actor, Bragg also curates the Leftfield stage at Glastonbury Festival.
He has been an opponent of fascism, racism, bigotry, sexism and homophobia, and is a supporter of a multi-racial Britain. He has long been a supporter of Labor causes and the struggles of class solidarity, particularly as it related to miners’ strikes in the U.K. and the U.S. He is the founder of Jail Guitar Doors, an organization that supplies instruments for prisoners to help address problems in a non-confrontational way.
Bragg is a regular of an annual event commemorating those transported from England to Australia for founding a union in the 1830s, has been an active voice in the Occupy Movement, and participated in Australia’s March in March anti-government protests. He called for the EU to intervene in a dispute between YouTube and independent labels, was a vocal supporter of the "civic nationalism" of the Scottish independence campaign, endorsed the Green Party in a recent election, and has promoted tactical voting.
He has just released Shine A Light, a collection of classic railroad songs recorded with Joe Henry in waiting rooms and at trackside in train stations from Chicago to Los Angeles. Bragg also has a new book in the works.