I enjoy going to conventions and concerts, and meeting people who had a hand in making the movies/music that I enjoy. I’ve gotten plenty of autographs for free (usually bands/musicians), but have paid for many signatures over the years, too - almost always in person at conventions.
I like decorating my game room with signed 8X10’s, posters, and props. I don’t think I’ve ever paid more than $50. The conversation is the best part, but it’s still fun to have a physical memory (for me, at least. I know it’s not for everyone).
Here’s some of my stuff (that Nightmare on Elm Street 4 poster is going to be signed by Robert Englund and a handful of other NOES 4 actors at a show in July):
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Let me know if you want to see close-ups of anything. I’ve also got lots of signed records.