The infamous black border set. I completed this about a year ago and I looked back through it, before this post. I'm kind of disappointed about the photography in this set.

This may be the first unanimous choice.

Cool action shot, with the pitch still in flight. 5 to 1, you can't identify the baserunner behind him.

For the longest time, this was my oldest Reggie card and it will always seem cool to me.

The World Series that made Robinson a legend. This card could only be cooler if the shot was zoomed in.

I'm always on the lookout for a cool Tiger card. It helps that he was my neighbor a few years ago. ToppsVault sold the photo for this card last year and I am still disappointed I lost out in the auction.
Honorable Mention:
Bert Blyleven
Joe Morgan
Roberto Clemente and Nolan Ryan (this happens when you are limited to 2 cards for each player).