Born in Vancouver, British Columbia, Robb moved to the United States with his parents, living briefly in Pittsburgh, before settling in Portland, Oregon, at the age of seven.

Following his graduation from Parkrose High School in 1974, he studied fine arts and music theory under Czech-American classical composer Tomáš Svoboda at Portland State University before receiving his baccalaureate degree in 1978.

[4] Through Jacobosky, Robb met guitarist Henry Vestine when Canned Heat performed at Murphy's and Me nightclub in Eugene, Ore., during their 1980 tour, where he was invited to join the band on stage and play Alan Wilson's guitar.

When Vestine later moved to Oregon, Robb helped him get established in the local music scene, and occasionally joined on guitar during Canned Heat's Pacific Northwest performances.

[8][9] In 1987, Robb's third recording, Nice Try, marked a departure from his electric band format in favor of solo acoustic fingerstyle guitar instrumentals and included guest performances by Fahey and Salgado.

[12][13][14] His second Burnside release, Stop This World, featuring guest artists Maria Muldaur, Eddy Clearwater and Curtis Salgado, topped the Living Blues Radio Chart in 1997.

[17] Robb's ongoing collaboration with Salgado, which included a national tour with Buddy Guy in 1995,[2] led to a brief interlude to Lucky Records in 1997 with the release of Hit It 'n Quit It.

[26] The album prompted Vintage Guitar writer Dan Forte to describe Robb as "...one of the best players, on acoustic and electric, embracing a range of blues styles and then some...", and feature an exclusive video performance of the title track song on its website.

[27][28] In 2019, Robb released Confessin' My Dues, his 15th solo recording and second album with NiaSounds, featuring renowned jazz musicians Gary Hobbs and Dave Captein.

[37][38] Released on Bone Clone Records, Purple Winos in the Rain features Callahan on vocals, harmonica and ukulele, with guest artists Peter Boe on piano and Robb on acoustic and bottleneck guitars, and a cameo appearance by Tom Waits.