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Brown was born on July 2, 1949 in the Hacklebarney section of Southeastern Iowa. His mother was an English teacher who played guitar, and taught her son about both books and music; his father earned his living as an electrician and scrap metal dealer, but also preached in a Pentecostal church on Sundays. As his family traveled throughout the Midwest, Brown soaked up a broad range of musical influences: gospel, blues, country, bluegrass, classical, and rock & roll. At the age of six, he learned to play the pump organ, and soon picked up the guitar from his mother. After graduating from high school, Brown enrolled at the University of Iowa; he signed up for a talent competition and won first prize, an opening spot at a campus concert by singer/songwriter Eric Andersen. Andersen liked Brown's performance and told the teenager he should consider moving East and trying his hand at a career in music. Brown needed no further encouragement, and soon quit school and headed to New York, where he found a steady gig at Gerde's Folk City, performing and running the weekly Hootenanny night. After a year in New York, Brown lit out for the West Coast, where he landed a job ghostwriting songs for Buck Ram, longtime manager of the Platters; while Brown said he learned a lot about writing on a deadline, he didn't enjoy life in Los Angeles and opted to return to Iowa.
He continued to write and perform after coming home, and for a while he worked as a duo act with his friend Richard Pinney; in 1974, they released an album, Hacklebarney, recorded during a show in Rockford, Illinois. The album sold poorly, and Brown didn't record again until 1980, when he self-released his first solo effort, 44 & 66. His second album, 1981's The Iowa Waltz, became a regional favorite, and the 1983 release One Night captured the intimate feel of Brown's increasingly popular live shows. Later in 1983, he teamed up with Bob Feldman, a St. Paul, Minnesota schoolteacher and music fan, to launch their own record company, Red House Records, which would in time become one of the nation's most successful independent folk labels. 1983's In the Dark with You became his first release for Red House; it earned enthusiastic reviews and sold well in the folk market, in part thanks to Brown's frequent appearances on the radio show A Prairie Home Companion. Brown's next release, 1986's Songs of Innocence and Experience, was an ambitious effort to set the poems of William Blake to music, and received enthusiastic reviews, as did his next effort, 1988's One More Goodnight Kiss. 1989's One Big Town earned Brown an Indie Award from the National Association of Independent Record Distributors for Best Adult Contemporary Album, and in 1993, he cut a duet album with Bill Morrissey, Friend of Mine, which earned them a Grammy nomination. 1994's The Poet Game brought Brown another Indie Award, and he released a second concert recording, The Live One, in 1995. After two more successful albums for Red House, Further In (1996) and Slant Six Mind (1997), Brown released 1999's Solid Heart, which was the first of several discs he's issued as fundraisers for various charitable organizations. 2000's Over and Under was a stripped-down project Brown opted to release through a smaller independent outfit, Trailer Records, rather than Red House; a second album for Trailer, Honey in the Lion's Head, appeared in 2004. Red House Records went through a change in ownership after the death of Bob Feldman in 2006; Brown released his album The Evening Call through Red House later that year, but for his next studio album, 2011's Freak Flag, he struck a deal with Yep Roc Records.
In his personal life, Brown has been married three times. He has three daughters from his first marriage, Constance Brown, Zoe Brown, and Pieta Brown; all three are musicians (Pieta has released several albums, with her father making guest appearances on two), and they performed Greg's song "Ella Mae" as a trio on the benefit compilation Going Driftless: An Artist's Tribute to Greg Brown. In 2002, Brown wed his third wife, fellow singer and songwriter Iris DeMent; he later covered her song "Let the Mystery Be" on his album Freak Flag. ~ Mark Deming, Rovi