Quoted from jesster64:

I have collected autographs for about 30 years.I have had literally thousands of signatures. Its a disease. Only paid for a handfull, Ali was $60 many years ago. I paid for one, but eventually got about 6 signed from him for free through the years. I had old magazine he signed cassius clay on it even though I didn't ask. Next guy in line asked and was told no. He pointed towards his picture and said he was Ali in that one.
I spent a good chunk of time running around and collecting autographs. I got ted danson to sign a cheers jacket, but had to buy his book. I was last in line and he only signed one item besides his book, and that was my jacket.
I paid a bunch of the james bond women to sign a poster at chiller autograph shows through the years, Will post picture later.
I did recently buy a mel blanc autograph at estate auction. Funny thing about that auction. I spent a fortune. But the estate belonged to a long time well known in person collector. They sold hundreds of autographs that day for peanuts.
Biggest jerks I've asked for signatures, michael jordan, kareem abdul jabbar, and bruce willis.
Best signers, boxers. They are so happy when you ask them to sign something. Its like they appreciate the recognition for all their hard work. I used to get arturo gatti all the time. I think I had every champion for the past 40 years signature on something.
I gave my wife (now ex) a gift for our 20th anniversary. An album that took me 3 years to put together. 150 autographed photos inscribed To :">($# Happy 20th anniversary.
I will pay, usually up to $20 if it is an unusual item and I want a neat signature.
I had 3 of the monkees sign a monkeemobile. I tried to get nesmith, but he wasn't signing, so I got so pissed I sold it. I was told "its not his thing", signing. Now I see he goes to chiller shows and signs for a price. All of a sudden, it his thing.
hundreds of stories and memories

Quoted from jesster64:

raquel welch would only sign her book. she said to send everything else to her fan club. At least I got to meet her. Still hot.

Quoted from J85M:

I paid to attend a bodybuilding seminar in London a couple years ago with Arnold Schwarzenegger the greatest bodybuilder in history as a special guest speaker, had back stage access and managed to nab a couple of signatures off Mr Schwarzenegger for my troubles!