Right now: Witch Image by Ghost. I actually created a playlist to keep track of all the songs that get stuck in my head a while ago, and I’m up to ~36 hours of songs so far. Shuffling that playlist never disappoints, because they’re all songs I’ve been listening to in my head anyway.
I always thought the GameCube controller was ridiculously comfortable and ergonomic, so that’s my choice. The C stick might not be for everyone though.
Any Dreamcast fans here? Those controllers had similar ergonomics in the hand, although the lack of a second analog stick was a pretty big drawback in hindsight.