22. Riding in Cars with Boys (2001)
For those of you hoping that this film is resplendent with scenes involving Drew Barrymore physically inside of cars with individuals who identify as male on the U.S. Census, we're so, so sorry. It's a cold world, what else is there to say?
You were hankering for a film that explores members of both genders, in automobiles, together, but this is really a melodrama about a young woman overcoming poor life choices. That's the thing about those shady Hollywood types, they always promise you one thing and deliver another.