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He's not about pursuing what other people think he should, he's going to pursue what he thinks is right for himself. His father (John Ashton, Beverly Hills Cop) is riding him to go to college, but Keith would rather stick to art.
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This same headstrong nature is also Keith's real virtue. He was the kid who was never let in the club, and Amanda is his key of entrance. He may be a little too concerned with how he's perceived, and Amanda becomes his revenge on the boys who made him feel small.
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By the same token, Keith isn't all noble ideals either. She's aware of her position in the world and how people perceive her. He rightly believes that she would never intentionally hurt him, and it's to John Hughes' credit that he doesn't make Amanda a villain. His ego bruised, Hardy poses a real threat to Keith's well-being, but not one to lie down and take it, Keith decides to continue to buck the system and take Amanda out anyway. Though not a rich girl herself, Amanda dates the richest jerk in school, Hardy (Craig Sheffer). When Keith asks Amanda out and she says yes, to most people he has done the impossible. The approach is a tad more serious than Pretty in Pink, and the fairy-tale ending is a happily-ever-after of a different color. The one thing he is oblivious to is the best friend of the opposite sex who is absolutely in love with him, in this case a punk rock drummer named Watts (Mary Stuart Masterson). Instead of a redheaded girl fantasizing about the prom, Some Kind of Wonderful is about a redheaded artist, Keith (Eric Stoltz), who dreams of being with the most beautiful girl he could ever paint, Amanda Jones (Lea Thompson). Writer/producer Hughes and director Howard Deutch return to the same plot idea: a love triangle between a creative, lovelorn romantic from the wrong side of the tracks, the best friend, and the dream date who floats through a different social clique. It's often derided as a retread of Pretty in Pink, but the reality of it is it's not really a retread, but rather, the male flipside. Released in 1987, Some Kind of Wonderful was the caboose of the John Hughes teenage train, and as a result, it has ended up being his most underrated film in the genre.