Obscure Answer

 Norman Mingo did it first with issue #35.
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Back #35 Front #35

It took another 29 years before Mort Drucker dared to do it again with issue #266.
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Back #266 Front #266

Richard Williams showed Jabba The Hutt's tail extending to the back of issue #354.
Good catch, José!
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Back #354 Front #354

Chances are slim to nothing you'll see this happen again in the future
unless Mad decides to continue a back cover advertisement to the front cover some how...

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