Holy Batglut!
The Batman movie series has figured prominently on the covers of Mad. If you count the reference to the TV series on issue #105, we've seen the pointy-eared one a total of seven times. And if you count the fact that issue #359 had four (cheap gimmick) cover variations and issue #455 had two cover variations, Batman has had eleven official appearances!
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| #105 | #289 | #314 | #337 | #359 | #455 | #492 |
Runners up are Harry Potter with five covers and Raiders of the Lost Ark (Indiana Jones), Star Trek, Superman (if you include Smallville) with four covers, and Rocky with three covers. Rocky, Rambo and Drudge Dread have given Sylvester Stallone six covers. That might put him in second place since he's the same character in every movie he does.
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