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

About this episode

The episode dives into the cultural impact and character analysis of 'Pretty in Pink' and 'Some Kind of Wonderful'.

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…

People in this episode

Hosts: Jason, Dee

Guests: Jill McCormick, Melissa Mingle

Topics covered

• John Hughes films
• teen romance
• film analysis
• character breakdown
• 1980s culture
• soundtracks

Keywords

• Pretty in Pink
• Some Kind of Wonderful
• John Hughes
• 1980s films
• teen movies
• character analysis
• soundtrack

Mentioned in this episode

Organizations: John Hughes, Howard Deutch

Books & works: Pretty in Pink, Some Kind of Wonderful

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