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AXO throws a Mr AXO male "beauty contest" every fall.
Lambda Chi always gets high marks in the talent competition part. One year they entered a guy that supposedly looked like Justin Timberlake (I don't really think so, but hey) and he and 4 other brothers were N'Sync and they did "Pop." Supposedly the judges loved it.
So maybe take a song that is really popular now... OR (my personal favorite) do a song that was popular in another era and have him dress the part.
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