9. KRISTY SWANSON AS VANESSA IN BIG DADDY (1999)
In Big Daddy, the aforementioned Joey Lauren Adams represents all that’s great about women; Kristy Swanson, Sandler’s gold-digging ex in the flick, is the antithesis. Angry at Sandler’s character for his lack of motivation, Swanson’s Vanessa dumps him and shacks up with a wealthy senior and his "old balls.” If she weren’t so damn hot, we would’ve kept Swanson’s money-grubber off this list. But, even when our dude Adam picks a heartbreaking dud, she’s a visual treat. He’s not as dumb as self-righteous critics might think.