As a general rule, Reese Witherspoon is the marker of a "chick flick." Ugh! And with the sole exception being Legally Blonde, her's (and all chick flicks for that matter) are silly, bland, safe, unfunny, commoditized fluff that pretty much s*ck. So if you get roped into one, you better be d*mn sure the lead is smoking hot or your lady friend is willing to do some late night trading if you promise to watch it attentively.
However, I would like to carve one of Reese's films out of the chick flick mix entirely, her debut, Election. It's an incredible film from almost every angle including American Pie good ol' boy Chris Klein (playing the same character here and seemingly not playing much of anything else since then unless "with himself" counts). And Matthew Broderick is hilarious as always. But Reese, as Tracy Flick (of all names), is as far from chick-flick Reese as you could possibly get. She drives this little film right into the big leagues with her incredibly uptight and do-good portrayal of a student set on becoming the student council president at all costs.
FilmBender is Funny Movie Reviews. Behind the lens is Alexander Payne who's also brought us a couple of other great films like About Schmidt and Sideways. I should probably give some credit to him here as well, but Reese is just so annoyingly amazing, smart and funny that she somehow managed turn me on and forgive her for nearly every single chick flick she's made since.