Year: 2008
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As part of a WrestleMania's focus on incorporating wrestlers, the top-notch boxer know as "Money" was the big draw for WrestleMania XXIV. Going into a feud with Big Show, Mayweather kicked off the angle at No Way Out 2008 by making an appearance to help protect Rey Mysterio, clocking Show right in the nose. He legitimately broke his nose and left him bloody. Along the way, Money oscillated between being a heel and face; WWE audiences just weren't taking to his brash and egocentric character.

Still, the angle was totally worthwhile. Money would appear in vignettes leading to his big match, with the finale being a No Disqualification match against Show. Money scored the win in the end, just barely escaping.

Mayweather would later host WWE Raw in 2009. Past that, Triple H would continue the WWE/Money connection by walking Mayweather out to his 2012 bout against Miguel Cotto. Weirdly, Justin Bieber and 50 Cent also performed walk-out duties for Mayweather at the same show. Wonder what all their locker room banter was like.