Ryan Adams and I go back to his Whiskeytown days (meaning: I started listening to him in 1995, while Ryan, well, he doesn't know who I am). Since going solo in 2000, he's taken a careening run through 27* genres of music over the course of 323* albums (these are estimates, but Ryan's made a lot of music).
He also just released a song-by-song cover of Taylor Swift's entire 1989 album.
Although his albums Heartbreaker and Gold are damn near perfect as they sit, I've built a lot of Ryan Adams playlists over the years; reconfigured super albums based on whatever emotional/spiritual jag I happened to be on at the time. (I do the same thing with Prince, another prolific guy who I'm sure would also hate me for re-sequencing his work, but, alas, another guy who also doesn't know who I am.)
Ryan's a man of many moods. I might suggest this mellow sampler when you're sipping bourbon by a late fall fire, wistfully.