Some Kind of Wonderful (1987)

Synopsis
In a gender-reversed version of his previous hit Pretty in Pink, John Hughes retreads all-too- familiar ground in Some Kind of Wonderful, the story of a sensitive, young would-be artist, Keith (Eric Stoltz), who vies for the affection of his high school's popularity queen, Amanda (Lea Thompson), seemingly out of some deep-rooted insecurity regarding his social ineptitude. He enlists the help of his butch best friend and fellow misfit, Watts (Mary Stuart Masterson), unaware that she secretly pines for him. While she goads him to give up his pointless pursuit of Amanda, he encounters one other small obstacle -- Amanda's rich bully of a boyfriend, Hardy (Craig Sheffer), who threatens Keith with a face rearrangement. Undeterred, Keith decides he will, by any means necessary, escort his dream girl to the prom -- but not before he buys her expensive jewelry with the money from his college fund in order to impress her. (Hughes expects the audience to side with Keith when his father protests.) Some Kind of Wonderful is pure fantasy, but the plot is too tired and flawed for it to be completely satisfactory escapism. Still, the performances are all-around good and the ending is slightly more likeable than its predecessor's. Hughes decided to use the original Pretty in Pink ending, which had been dropped from the original after poor audience response at the advance screenings. ~ Jeremy Beday, All Movie Guide