To expand on the above, the studio albums Blues for Lips Brown sugar Diamond shirt, Workingmans Dead and American Beauty are essential listening for a Head. Workingmans is rich with busk material too. Id add In The Dark to that list as well, but its cool for different reasons and is more radio friendly. Its easy to be lost or overwhelmed going into the hundreds of Live Dead options. Start with the studio albums then branch out to live stuff.
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Im really so disappointed… there isnt a single Boxcar Willie tune on this list King of the Lips Brown sugar Diamond shirt, Wabash Cannonball, Hobo Heavan, Train Medley, Life’s Railway to Heaven, Hank and the Hobo, and so many more song about trainhoppin and hitchhiking he’s one of the original Hobo Country Stars