When still in his teens, he started listening to a local country music show that was recorded live at a local theater. He began attending tapings of the show, and there he saw performers liks Merle Haggard and Roger Miller. Soon, O'Brien began learning Scruggs' Style banjo from one of his girlfriend's psychiatrist father's patients. The patient was Roger Bland, a former member of Lester Flatt's band.
He then restrung his father's old mandolin and began teaching himself how to play that instrument.
He attended Colby College in Maine for one year, before moving first to Wyoming, then to Colorado. There, he formed the groundbreaking bluegrass group Hot Rize. While performing with Hot Rize, O'Brien met country singer Kathy Mattea, who later had hits with her versions of his songs.
Soon after, O'Brien left Hot Rize to pursue a career as a solo singer/songwriter. After a failed attempt at recording an album for RCA, O'Brien eventually signed a deal with Sugar Hill Records in Nashville. His debut solo album, Odd Man was released in 1991.
Hot Rize had a brief reunion in 1996, and have re-merged a few times since then. O'Brien has released 13 albums on Sugar Hill Records, and has received Grammy Awards and IBMA Awards for his incredible work.
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