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Phelps concentrated on free jazz and took his cues from musicians like Ornette Coleman, Miles Davis, and John Coltrane. He spent 10 years playing jazz, mostly as a bass player. He refers to his "conversion" to a blues musician when he began listening to acoustic blues masters like Fred McDowell and Robert Pete Williams. He initially gained notice for his solo lapstyle slide guitar, which he played by laying the instrument flat and fretting it with a heavy steel bar. Inspired by the birth of his daughter Rachel in 1990, Phelps began writing songs. He began singing and released his critically praised debut, Lead Me On, in 1995. This album showcased Phelps' craft, and as well as his own songs, he tackled traditional numbers such as "Motherless Children" and "Fare Thee Well." In later albums, he has incorporated more ensemble work.
His fourth album, Sky Like a Broken Clock, appeared in 2001. This time he added a bassist and a drummer to the production. That album's companion piece, the Beggar's Oil EP, was a critic's favorite in 2002. In order to achieve a richer, orchestrated sound on Slingshot Professionals, released in 2003, he gathered a wider collection of musicians to play guitar, bass, drums, mandolin, violin, and accordion.
In 2005, Phelps released a live album, Tap the Red Cane Whirlwind, which he followed a year later with the studio album Tunesmith Retrofit. In 2009, he released an album of instrumentals titled Western Bell. Following that release, he began recording and touring with the American singer-songwriter Corinne West. In January 2013, he announced a hiatus from touring due to ulnar neuropathy in his right hand and arm.
Phelps is featured in the 2011 book I'll Be Here in the Morning: The Songwriting Legacy of Townes Van Zandt. In 2017, he was profiled in the eclectic UK music blog the Immortal Jukebox.