The Howard Stern Roast 2000 

He’s easily the most self critical person in showbiz

That's sort of the joke. There are lot of levels of irony to the show. Part of it is setting up Jackie for his chance to finally get back at Howard for relentless ball busting and then doing two weeks worth of bits afterwards about how bad Jackie bombed. Additionally, Fred works the soundboard and isn't responsible for who he hits the applause button for, and Howard can't really be seen laughing at jokes directly cruel to his ex wife.

Take what? Its his show. He put it on the show and wasn't the first roast.

HS roasts himself everyday

Reported for copyright

​@@JohnMezcal 😂😂

Fred had to get his nose dirty to stay on that show

@@ChristopherIanMacfarlane He was really kissing howards ass at this point

Fred can't handle criticism. On the flip side, it was Jackie's most endearing quality. He could get his balls busted relentlessly and stay in character. The show needed someone to ridicule. The joke here is that Howard was finally supposed to be on the receiving end of a roast, with the ironic twist being that it ultimately turned into everyone shitting on Jackie for how hard he bombed for the entire next week. Jackie went up all excited thinking it was his time to roast Boss, and ended up the butt of the joke somehow. You need to understand the show and understand that these are all bits that the staff worked on and wrote behind the scenes to make funny. Either just enjoy the comedy for what it is or learn to understand the creation of the show. But don't over-analyze the complete wrong stuff man!

He was

I listened to something the other day where they did a “crazy” test Ronnie was the worst and Robin second worst and Howard said it was accurate she was in fact nuts. She disagreed!

Then you have listened long enough.