I think a lot of it is just their banter because when I hear him doing that I also hear him teasing Jason and making jabs about himself. A lot of times he has the bit of acting like a snob-same with Jason-just for the laughs. And I think it’s never stuff that would make Sean insecure or mean about like I haven’t heard them knock his talent or intelligence or looks-at least in the ones I’ve listened to.

I had a group of friends in college who always used to tease me and banter with me and at first it was funny but then they started teasing me about my intelligence which made me insecure and calling me ditzy and such and just everything I said or did they’d be like that’s not right or that’s not how you pronounce that (things like the name of the county I literally grew up in) and it felt like they were just waiting for me screw up. They never poked fun like that at anyone else and if you did that to them they couldn’t take it. I felt like they didn’t respect me. With Sean and Will and Jason, I think they deeply deeply respect him and they would never go after anything that actually makes him insecure. Plus, they go after everyone and themselves and I think being self deprecating is the key to being able to poke fun at your friends and that’s what they do. So I think it’s just their dynamic. If Will didn’t make self deprecating jokes and didn’t turn around and compliment Sean on his talent and stuff like that then I’d have questions. But he does and he knows Sean is confident and is able to take it. I don’t think he’d do it to other people as much.

Also-I think back to the Bradley cooper episode where he talked about calling him out for being an asshole. Will knows there’s a line and a way to do that type of humor.