Pines cut his teeth playing summer festivals on the west coast and busking on the streets of New Orleans with the Kitchen Syncopators, a band he started in 1998 with Gill Landry. After four years obtaining a musical education in New Orleans -- while living poor and occasionally paying rent with wine and Lucky Strikes -- Pines left the band and headed north to Ohio. He recorded a solo album titled Rags to Riches in 2006 and followed that with two more the following year. The first, a lo-fi garage recording, was called Lonesome Shack Blues, while the second was a self-titled album recorded under the moniker Woody Pines & the Lonesome Two. The "Lonesome Two" consisted of Tim Peacock on bass and Bram Riddlebarger on drums.

The band Woody Pines was formed in Athens, OH, in 2008, and mixes all of Pines' many influences into one down-homey blend of ragtime, country blues, roots/Americana, rockabilly, and New Orleans-style jazz. The following year, Pines moved the band to Asheville, NC, and recorded Counting Alligators. Pines played his customary lead role, handling guitar, harmonica, and vocals, with Zack Pozebanchuk on upright bass and Andy Tubb and Rennie Elliot splitting drum duties. Counting Alligators was recorded by Pines' old friend from his Kitchen Syncopators days, Gill Landry, who in 2008 replaced Critter Fuqua in Old Crow Medicine Show. Landry also plays on several tracks, as does Old Crow member Ketch Secor, who lends his fiddle. Another fiddle player who assisted with the album, Darin Gentry has since become a full member of Woody Pines. Tubb and Elliot were also replaced on drum by Nathan Taylor, who plays a stripped-down snare drum, similar to Slim Jim Phantom's percussion role with the Stray Cats.

Comparisons between Woody Pines and Old Crow Medicine Show are easy to make. Both are part of the hip, younger generation of traditional string bands that have helped to revive an interest in a music from a bygone era, and both learned their craft through immersion and years of busking. However, Woody Pines' sound is much more steeped in the old ragtime feel of New Orleans than that of Old Crow. Pines, himself, it should also be noted, has a bit of a reputation as a virtuoso on the kazoo. ~ Chris Berggren