Old Crow Medicine Show is what happens when a string band commits to playing recognizable folk and country songs at the speed of bluegrass. The chord vocabulary is small. The rhythm is the whole game. If you can strum a clean three-chord progression in G or A, you can play most of their catalog, you just need to do it faster than feels natural at first.
Wagon Wheel is on this site already, and it’s worth saying out loud: this is the song every guitarist in the United States ends up learning. Capo on the second fret, three chords (G, D, Em, C as the I, V, vi, IV in A), and a steady eighth-note strum. Once that’s clean, the rest of the catalog opens up because almost every song uses the same setup.
The next step after Wagon Wheel is Tell It to Me. Same capo position, same chord shapes, but the tempo is fast enough that you have to commit to the strumming hand. This is the song that turns a learner into someone with stamina. Sweet Amarillo at a relaxed waltz feel is the alternative if you want to practice 3/4 time with the same vocabulary.
What’s worth borrowing from Old Crow’s playing is the trust in repetition at speed. Bluegrass and old-time music keep the harmonic structure simple precisely so the band can focus on the groove. The lesson for a beginner is that rhythmic confidence beats chord vocabulary every time. A clean three-chord song played fast and tight will sound better than a six-chord song played hesitantly, and Old Crow’s catalog is the right gym to build that confidence in.