Well, back in 1980. I was a fan at the Chicago Comic Convention (was that the name of it?) and was hoping I could get a drawing from John Byrne. The crowd was too dense around him and I never got close enough to ask. At least I think that was the case. My memory's a little vague about it. I do remember however that Frank Miller was sitting by himself with no one around him. He had just recently become the penciler on Daredevil. I had a portfolio of drawings and asked him if he would do a drawing of a character I had created. He was charging $15 a sketch. The results are above. (Yes, as a teenager, I was a fan of Batman and Iron Fist. Why do you ask?)
At the same convention, Joe Rubenstein inked a panel on a page I had penciled featuring a What If idea I had where Spider-Man retained his four extra arms. Seen here.
By the way, the first comic job I ever had was writing and drawing a story for DC's Talent Showcase # 18 in 1985. You may recognize the character from earlier in this post..!