Day Two: Spider-Man
I think H is right: There aren't a lot of really distinctive, iconic Spider-Man covers. Which is surprising: Given how flippin' many Spider-man covers there are, you'd think the odds would be on their side.
The first fifty issues have far more than their share of gotcha covers, even though some of them are cut-and-pasted from Ditko's interior pages. On this cover to Amazing Spider-Man #22, Ditko attempts Batman's menacing shadow, which shouldn't work and probably wouldn't have worked if not for the Spider-signal belt buckle. (does he still have that?) It turns an off-center pose where the hero of the book isn't even present into a striking, moody piece. There have been dozens of attempts to use the signal motif since, none as effectively as this.
Oh, and the interiors aren't bad either.
The requirement to select covers from distinctly different eras of the book forced me to choose only one Ditko cover -- and also eliminated the best of John Romita Sr's covers as well. I probably could have considered the Andru run a different era, but despite countless classic images for Wonder Woman, I have to say I never liked his Spider-Man.
And Todd McFarlane's work always looked too busy to me. Lookit me, I drew all these extraneous web lines, aren't you impressed by all the work I did here?
As long as I'm flashing forward, I'll go all the way to Friendly Neighborhood Spider-Man #4, the end of "The Other" arc. Not having approved of the trials and reboot inflicted on the character throughout "Sins Past", "Civil War", "Back in Black" and "One More Day", I consider this gorgeous Weiringo portrait the end of Spider-Man's run. I prefer to remember Pete and MJ looking forward to the days they should have had, and it doesn't get any better than this.