From 1987-1995 he studied philosophy and history at universities in Tennessee and Wisconsin, paying his way through by playing in several bands which performed on the college music and fraternity party circuits of the time.

Singing lead and playing fiddle, mandolin and guitar, Wheeler recorded an album originally titled AC/Dixie[4] along with local Nashville bassist Kurt Carrick, dobro player Mike Daly and guitarist Rusty Horn.

[5] In March 2003, the band had the unique distinction of having 3 different albums in the top 15 of the bluegrass category of the US Billboard charts at the same time,[6] Wheeler is also the songwriter for the majority of Hayseed Dixie's original songs,[7] including the cult hits "I'm Keeping Your Poop (In a Jar)"[8] and "She Was Skinny When I Met Her."

Currently residing in Cambridge in the UK, Wheeler has recently appeared as a special guest on BBC Radio 2 programs, including The Chris Evans Breakfast Show[9] and Simon Mayo Drivetime.

An EP of original Southern country-rock drinking songs, titled Daydreams About Night Things was released on January 26, 2018.