In the 2000s, when he wasn’t shagging starlets or performing stand-up comedy, artist was leveraging his two distinct gifts: His virtuosic guitar skills and his aptitude for classy pop-rock songs. Putting those abilities to use both on his solo albums and with the band, his blues-rock group, the artist earned big chart success, becoming the sensitive singer-songwriter of choice for hordes of Americans.
The middle son of two teachers who grew up in Fairfield, CT, he picked up guitar at age 13 and was soon playing local blues clubs both solo and with the band Villanova Junction. At 17, he suffered a cardiac arrhythmia that kept him hospitalized for a week. It was then that his songwriting career began in earnest. A year after finishing high school, the artist enrolled at Boston’s Berklee College of Music on a partial scholarship. He dropped out after his first year to move to Atlanta and play live with his friend Clay Cook under the name LoFi Masters. He left the duo to record his first EP, 1999’s Inside Wants Out, which he distributed himself while playing gigs across the South.