When I was still in high school, I used to buy the heck out of the quarter-bins from my first LCS. But the first time I paid REAL money for an older comic which it was then, it was $15 for Green Lantern/Green Arrow #76 (signed by Neal Freakin' Adams) and $20 for Avengers #57 (1st App. Vision).
Which was yours?
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When I was very young (way before I had a checking account of my own), my grandmother used to purchase backissues of The Incredible Hulk for me via mailorder, first from Richard Alf (twice), then through Mile High Comics (which bought him out). Most of those issues were in the $2-3 range IIRC. My biggest regret is not buying issue #1 for $30, but that was so far beyond the realm of possibility I never even asked.
After I had a checking account and driver’s license of my own and my Hulk collection was complete, I used to hunt down backissues of the Avengers. Most of those were in the $3-5 range at the time. Although I did eventually acquire all of the Lee/Kirby issues, I don’t recall how or when or how much I paid.
For our first wedding anniversary (paper), my wife bought a copy of Green Lantern #40 for me, but because it was a gift, I don’t know how much it cost.
There aren’t just too many backissues I want that I don’t already have. The most I remember paying for a backissues recently (within the last five years or so) is $10 for Jonah Hex Spectacular.
Our Army at War #237, October 1971. I paid a whopping $7 for it, which, at the time, was more than I could afford. To this day, I can't pay more than $7 for a back issue, even though that $7 would be about $18 today. (Yesterday, I was at my friendly neighborhood comics shop, and I saw a one-shot from DC at $6.99 and shuddered.)
Mark S. Ogilvie said:
If you like, I'll sell you an old issue of Youngblood for a whole lot of money. That'd be memorable.