Sharon Simmons, 55 - Dallas Cowboys (2012?)
Good news for football fans with a mature fetish: 55 year-old Sharon Simmons is trying out for the 2012 Dallas Cowboys cheerleading squad (there she is pictured above, in all her sinewy, sun-damaged glory). If she can successfully demonstrate her flexibility, stamina, and ability not to crap her hot pants during jump splits, Sharon will become the most chronologically advanced cheerleader in NFL history. But she wouldn't be the first MILF or GILF to earn a spot on a pro cheerleading roster. Here's a tasteful look at the 7 oldest and boldest ladies to ever grace the sidelines.