This one is Dupree's Diamond Blues" by the Grateful Dead. Talks about a man going to drastic measures to please his girlfriend or wife (not specified). He finds that his "baby" has been cheating on him with the Judge that sentences him. He is easily replaced with a richer simp. Based on Frank Dupree who was executed in 1922.

Here are the lyrics: http://artsites.ucsc.edu/GDead/agdl/dupree.html

And the song: https://youtu.be/YK3f4SwNCTk