I think Warren Zevon. He had that humerous, intellectual bad boy schtick down pat with some self-destructive tendencies. He was apparently "to the right of your father and Ronald Reagan" (Source). Here's an example of the dude's lyrics:

I listen to songs like "Lawyers, Guns and Money" and "Desperados Under the Eaves" and I just hear a world-weary bitcoiner who would down a few brews at a lobbycon.