Some Kind of Wonderful is the less iconic, gender-swapped cousin of Pretty in Pink (both are written by John Hughes and directed by Howard Deutch), but what it lacks in renown, it makes up for in nuance. It goes a bit deeper in its exploration of gender roles and class disparity, really digging into the important differences between its female leads and the privilege of its wealthier characters, and it’s just as funny and charming too. Sure, a big part of the delight of watching it stems from nostalgia, but a larger chunk comes from the actors’ easy chemistry and the script’s witty lines. The movie is not revolutionary—it’s just a romcom at the end of the day—but it is smart and subverts expectations when you least expect it.
Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and tries to convince him to stop pursuing Amanda. Matters are further complicated when Keith's invitation draws the ire of Amanda's rich yet snobby ex-boyfriend, Hardy Jenns, who makes plans to get even.
Keith (Eric Stoltz) pursues an out-of-league Amanda (Lea Thompson) despite the warnings of his tomboy best friend Watts (Mary Stuart Masterson).
That banger of a last line. I won’t say it here, but if you know, you know. Also, “It’s 1987! Don’t you know women can be anything?” “I know, my mom’s a plumber.”
Growing up is finding the dad in a John Hughes movie the most relatable and sensible character in the movie.