Most Infamous Moment: In late 2004, photos surfaced of Reid on the red carpet at P. Diddy's 35th birthday party. She looked great, except for her exposed and recently augmented left breast.

With her Playboy spreads, red carpet nip slips, TMZ covered drunken antics and subsequent stints in rehab, we can assure you that this infamous actress is not the mild-mannered virgin we met in the first American Pie film.