19. Selma Blair as Cyrus, Down to You (2000)
In no way are we recommending that you watch a romantic comedy starring Freddie Prinze Jr. Released at the height of his very short tenure as a C-list leading man, Down to You is notable for making anyone foolish enough to watch it feel seriously bad for co-star Julia Stiles. Paycheck jobs are understandable, but she really deserved better.
The same goes for the always button-cute Selma Blair, though at least she had the good sense to use a Freddie Prinze Jr. movie to try her hand at playing a porn star. Blair must have figured, "Nobody's going to see this bullshit anyway, so why not have a little fun?" Amen to that.