"99 Problems" is a classic. Consequently, "99 Problems"-referencing attire will never really get old. Undertaker is old, but he's a legend who's still relevant enough to take small joy from the picture you see above. The Calaways (he married wrestler Michelle McCool in 2010) are happily married, so the reference fits.
Still, this raises another question: Does the Undertaker really have 99 problems? He's too old for this. Plus, he's the Undertaker. The main point of his personality is how he takes care of problems. What does anything mean anymore?
Anyways, cool pic.
[via Michelle McCool]
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