Sorry to resurrect this post from the dead, but a couple of stories I thought I could share.
In the early 90s, I was a real autograph "hound" in minor league stadiums, and attended every baseball HOF induction ceremony from 1987-99. I was a know it all kid, who had balls of steel going up to athletes, and never really got intimidated or starstruck. As many people who have been to HOF Induction Weekend can attest, the golf course is a good place to try and score some free autographs. In 1991 I was walking back from the golf course and thought to myself "I wonder if any HOFers ever play tennis?" So I walked past the tennis courts. To my surprise, Ted Williams was sitting on a bench watching some people play tennis. I just happened to have this 8x10 with me. I am not even sure if I even said anything to him, I was so nervous. To this day, I really think it was the only time I have ever been starstruck by anyone.
In 1996 (I think), I was walking down Main Street in Cooperstown, when I hear a car honking. I look over, and it's Phil Rizzutto driving, and his wife in the passenger seat. He's honking because I am carrying a Phil Rizzutto lithograph, and he's giving me a thumbs up. I was pretty excited about this, and I never even thought about going over to the car to see if he would sign it (DUH!). Now I HAD to get this lithograph signed, just because of the story behind it, so I paid to have Scooter sign it the next year in Cooperstown.
On the flip side....In 1995 (I think) I see Reggie Jackson walking down Main Street of Cooperstown. Just a backstory, Reggie was my favorite player growing up. Although I was young, I would always tell my Dad to tell me when he was going to be at bat for the Yankees because I wanted to watch him bat. I still remember telling my Dad that one spring, and he said "Scott, Reggie doesn't play for the Yankees anymore". Anyways, Reggie was all alone, and no one seemed to recognize him or be bothering him. I went up to him with a Perez Steele postcard and asked him to sign it. Instead of signing it, he informed me of when, where and the pricing for all of the paid signings he would be doing that weekend. It probably took him 10x longer to explain all of that to me than to just sign my postcard. Stupidly, I actually paid for him to sign it....when I look at it now I am still bitter about that. Although I did get a bunch of Reggie items signed at Cooperstown in the mid90s and got free inscriptions at the time such as "HOF 93" and "Mr. October" without paying.
Lastly, I was on a plane one time with Scotty Bowman and got my picture taken with him on the way in. Seemed very friendly, but in the picture he doesnt look happy at all. I was with a buddy who wanted an autograph, and he asked me for one of my business cards. Scotty Bowman signed one of my business cards for this guy.