85. Tara Reid
Wifey Of: Tom Brady, New England Patriots (NFL), Kyle Boller, Oakland Raiders (NFL), Jeremy Shockey, Carolina Panthers (NFL), Sergei Fedorov, Detroit Red Wings (NHL)
While popular culture may have long since forgotten Reid, she has nevertheless managed to go on a fine run through the professional sports ranks. She started her career in 2002, dating emerging star Tom Brady for about a month. Reid further wetted her football player appetite in 2003 when she went out on a date with Jeremy Shockey (they attended a Red Hot Chili Peppers concert. No word on whose parents chaperoned). In 2004, Reid tried out another quarterback, former Baltimore Kyler Boller.
Perhaps sensing that football players were a bit of a dead end for her, Reid then moved on to Detroit Red Wings great Sergei Fedorov for a brief spell at the end of 2004. She seems to have learned her lesson, and no longer dates athletes.