I never looked too closely at the lineage of You Win Again. The fact that it appeared on Europe ’72 makes it a “classic” cut of sorts despite the fact that it was only played 24 times in late 1971 and 1972.
I’m sure I noticed at some point, but forgot until I was grabbing the link to the lyrics for the song here, that this was originally a Hank Williams tune. It serves as a good reminder for me how many different types of blues are out there, this being more in the country blues vein. You can really hear it in the approach and the rhythm section. I think that having an acoustic piano in the mix really helped to give You Win Again the feel it needed. In other words, Keith adds a lot to this little ditty.
In looking at the lyrics, it was also kind of interesting that Williams sang two additional verses in the original. I’m left to wonder why Jerry didn’t include those. It’s not like the Dead were averse to long song, but perhaps that was intention to keep it short. Who knows?!