Crowley from Supernatural

VS 

Alastor from Hazbin Hotel

The King of the Crossroads vs the Radio Demon.

So this match-up just randomly popped into my head while rewatching Supernatural. With Hazbin Hotel getting popular lately, I couldn't help but notice a surprising number of similarities between these two. Red demons with a sense of humor and dapper fashion sense, both playing the role of a deal making demon that rises to power. They tiptoe the line between being a master manipulator and being the heroes' literal best friend, and they always liven up the room when they make an entrance. My first thought was that Alastor would stomp because it's a cartoon demon vs a live action one. But on the other hand, Crowley has so much more source material and known abilities to work with, so many more tricks and spells, hex bags, and even angelic weaponry which would be his ace in the hole. Still, I'm pretty sure Al is faster, potentially could have his own angelic weaponry to use, and has shit Crowley just wouldn't know how to react to, like his giant form. From what I can tell, they scale to roughly similar levels of power, so it could come down to their unique abilities and magic.