"Pretty in Pink" (1986) vs. "Some Kind of Wonderful" (1987): Part 1

On this special two-part deep dive, Jason and Dee are joined by friends of the show and Patreon all-stars Jill McCormick and Melissa Mingle to tackle the final face-off of the classic John Hughes teen era: Pretty in Pink vs. Some Kind of Wonderful.In Part 1, the gang rolls back to the mid-’80s to unpack the origins of both films—how Pretty in Pink emerged from Hughes’ collaboration with director Howard Deutch and how Some Kind of Wonderful became the spiritual “answer song” to its predecessor. They explore the cultural moment, the soundtracks, and why these two films feel like emotional cousins… even if they land very differently. Then it’s time for a full character breakdown of Pretty in Pink, including Andie (Molly Ringwald), Duckie (Jon Cryer), Blane (Andrew McCarthy), and Steff (James Spader). The crew digs into performances, casting what-ifs, behind-the-scenes stories, and how each character hit us differently then… and now. Of course, we couldn’t avoid the big questions: The dress. Iconic? Overhyped? Misunderstood? Did Blane actually do enough to earn redemption? And which movie truly delivers the better bad guy? No final verdict just yet — the ultimate judgment is reserved for Part 2, where everyone will officially cast their vote and crown the champion of Hughes’ last great teen romance.If you’ve ever debated Team Duckie vs. Team Blane or wondered whether Watts could’ve walked into Shermer High and run the place, this episode is for you.Part 1 starts now. The final judgment is coming. Support us on Patreon: https://www.patreon.com/c/surelypodcast Follow us on YouTube: https://www.youtube.com/@surelypodcast Check out our new merch store: https://surely-you-cant-be-serious-merch.myshopify.com/