Was Drew Barrymore trying to go back to playing more "edgy" roles?
Prior to this, she was taking on decidedly more wholesome, "good girl" roles like Julia in The Wedding Singer, Josie in Never Been Kissed, and Danielle in Ever After. It was of course, a far cry from her Poison Ivy/Amy Fisher days, which seemed to be Drew just about embracing what people generally thought of her (before she got sober and presumably cleaned up her act) at the time. It's still kind of jarring to see Drew attempt to at "sexy" like the scene at the race track with her plunging neck-line and cleavage hanging out. Here, it's almost as if Drew is playing a virtual parody of her past (rebellious, crazy girl) self or image.
https://tvtropes.org/pmwiki/pmwiki.php/Main/ContractualPurity