Going to an Ivy league school, I have met many "celebrities" in sports. politics, business, and show business before they became famous. Some I knew or observed well enough to have "dirt" on them. But I am not gonna talk...
The first - and my favorite "celebrity" - I met was Jackie Robinson, who came by my grade school as a judge for our science fair. I got the chance to show him my project and tell him about it. Very nice man. More than a "celebrity", this is history.
In high school three of my friends and I went to see the Broadway Musical "The Wiz", and hung out at backstage exit after to show to get autographs. Most of the actors just said hi and walked past, but two of the stars - Stephanie Mills and Tedd Ross, stopped to thank us and signed and talked with us. I was surprised at how short Stephanie was. Ted said "I always do this, I owe it to people who come out and see my performances".
On one of my first Megacorp business flights I rode with Don Meredith and Frank Gifford when they flew into DC to do a Monday Night Football game. I got to chat with them a little at baggage claim. Don was very friendly and happy to chat. Frank kind of semi-glared at people, though he did smile and say "thank you" when I said I was a Giants fan (Don humorously rolled his eyes and said "O Lordy no..."
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I was at the 1984 LA Olympics, and at one of the track and field events I sat behind Bill Murray, Brian Doyle-Murray, and Harold Ramis. There were very funny and happy to interact with people around them and to talk about "Ghostbusters". At one point Haroid Ramis asked us "so how could we have improved the movie?"
The largest collection of "celebrities" I met at one time were a group of WWE (then still the WWF) wrestlers, at a breakfast place in an airport early early one morning in the 80s, after they had performed a show the previous night. There were probably a dozen of them there. I stood in line with Big John Studd - he was HUGE but very friendly. I got a table by myself, and then Roddy Piper and Paul Orndoff came by and politely asked if they could share it with me, since there where no empty tables. Both were nice, chiding me for not being at their show. Roddy asked to borrow the WSJ I had, asked me who I worked for, and asked questions about if my Megacorp was a good stock investment.
I sat next to Ray Lewis in first class, when he was still playing for the Ravens, flying out of Baltimore. He had the window seat. So many people boarding stopped to say hello and lean across me to chat him up or shake his hand, that, once boarding was complete, he apologized to me for all the folks leaning across. It was not a big deal to me, and we had a little small talk but mostly I left him alone. At the end he shook my hand and thanked me, and we wished each other well.
Through a family connection I have been able to meet Doug Pederson, coach of the Philadelphia Eagles, several times, both before and after they won the Super Bowl. A very nice friendly man. A few times through the connection I have sent humorous messages to him, and he has responded in kind.