After spending their first few years writing abstract psychedelic tunes, the Grateful Dead took a hard turn into Americana. They wrote a bunch of songs inspired by blues, country and folk, and in doing so, they massively expanded their listener base. Several of these songs involve outlaws and drifters in the Wild West. I think the best of the Dead’s cowboy songs, both lyrically and musically, is “Jack Straw”.
When I was a kid, my older stepbrother had a bunch of Dead albums stored in our apartment. I avoided listening to them at first because their covers suggested that they would be too heavy and frightening for my tastes. Imagine my surprise when I finally did try them and they turned out to be affable psychedelic country. I first heard “Jack Straw” on What A Long Strange Trip It’s Been, the hugely better of the two Grateful Dead greatest hits compilations. (The other is Skeletons from the Closet, which has some baffling choices – “Mexicali Blues”, why?)