Rich did the "other regis" joke in off-topic, so I'll leave those out. One of the sadder ones recently for me, Philbin came out of way left field for me as far as being cool/funny. Quick WAM-adjacent story if you want, otherwise just scroll down to the food fight clip (in unfortunately poor quality, man I have more 144p clips than I thought).
Hell if I can remember what year it was, I was probably ~18, and there was an episode of Regis and Kelly where there was some setup beforehand that Kelly had to stay silent for the entire show (or the first 20 minutes, something like that), and if she spoke, she would get slimed (this predated the several slimes she later took, WAM legend that she is). The story got some traction here, so I was on it that morning to record. And damnit if I wasn't laughing my ass off for that first segment of the show to Regis attempting to get Kelly to speak and her gamely staying quiet. I had never watched the show, and by all accounts the people hosting morning shows were not cool or funny, especially to my demo, but Regis surprised me, and I remained a fan since. Didn't start watching the show consistently or anything, but checked it out when I could.
Regis also gets solid WAM cred for this hilariously contrived food fight they staged to promo Kelly's new sitcom Hope and Faith (where there was a much better food fight in the pilot). The staged mess goes completely off the rails 2 seconds in when he gets shot in the eye with ketchup (love Kelly offering her shirt to wipe it, b/c of course they don't have towels or something out there), then Reg insists that Kelly hand him the mustard so he can slowly, deliberately squirt her with it. Then Tony Danza runs in and yeah, it's a shitshow. Not great for coverage, but some legit spontaneous comedy involving WAM. Thanks Reg, RIP.
Love you, too
