Gilbert was very shy, frail and soft spoken. Shook his hand and walked away but turned back and shouted "You performing in town?" to which he shouted back "Cobb's!" So I wound up going to see him with my pops. Sample joke: "Mackenzie Phillips said her father John Phillips used to sneak into her room and have sex with her every night when she was a kid- I can't even get my daughter to hold my hand when we're crossing the street!" RIP Gilbert
Craig Robinson was at a strip club with a couple friends dressed super casually. It was right around the time of "Pineapple Express" so my friend's gf quoted Craig's lines from the film to him which I'm sure he loved. Then when my friend and I was outside smoking, Craig came outside and my friend told him to extend his closed hand and proceeded to dump a small pile of coke on there, insisting that Craig partake.
Craig was understandably very reluctant- we were strangers he'd barely interacted with and we were standing at a very busy corner (Broadway & Columbus). But he took the whole thing like a champ, thanked us and walked off.
P.E.A.C.E. is hardly a household name so barely counts as a celebrity but on a good day he's my all-time favorite MC (go back and forth between him and his Freestyle Fellowship cohort Mike 9). But I was on a Haight Street bus and a friend called me to tell me that PEACE was at a nearby skate shop promoting his new album ("Megabite" so this would have been 2004). When I got there PEACE was obviously ####ed up and cracking everyone up by talking nonsense. He tried to give me a free vinyl copy of the album but I told him I already had it so he should save it for someone else but it was my favorite album of his.
I mentioned that the song "GonnaBeDope" was my favorite and he said he was on both shrooms and ecstasy when he freestyle that one (if you listen to the song it makes sense lol). He then compared me to "Extreme Elvis" (apparently an Elvis impersonator who does "Jackass" style stunts/pranks) and gave me a hug after I responded with "Thank yew thankyewverymuch!" in my best Elvis voice.