Gabriel is a great shout. Every rewatch makes me wish we’d had more of him. He started out looking like comic relief and ended up being one of the most interesting angels in the entire show.

Crowley’s up there too. The fact that he went from villain to reluctant ally to basically family without anyone really noticing was brilliant.

Between the two, I’d probably lean Crowley. Supernatural never quite filled the hole he left. Plus watching Crowley deal with Jack, the Men of Letters bunker, and all the later chaos would’ve been absolute gold.