Mom was good friends with Rick Reuschel's mother-in-law, so I got to meet him in my living room when I was around 7, (he was a starting Cubs pitcher)
Met Oprah in the shops of the Drake Hotel, very nice and personable, she was just getting to be insanely rich at that point and only ridiculously rich.
Gene Siskel and Roger Ebert at Roger's wedding, both very cool, and both missed.
Jeremy Roenick and Chris Chelios at a bar in Chicago, I was a bit lit and don't remember too much
Arnold Schwarzenegger at a book signing back in 1980 or so.
Joe Walsh at an impromptu concert at the North Beach boat house (Joe is possibly the coolest man on earth)
Steve Dahl (Very, very popular Chicago radio personality in the 70's, 80's and 90's)
Angelo Moore from Fishbone kicked me in the forehead when he did a stage dive at Metro, apologized, and I got to do a stage dive with him after that.
Tim Kazurinsky from SNL and Police Academy movies lived in a town I used to work in and met him several times. Incredibly nice, down to earth guy, would even initiate conversations with me