"Pretty in Pink" (1986) vs. "Some Kind of Wonderful" (1987): Part 2

In this second part of their deep dive into the 1980s teen classics 'Pretty in Pink' and 'Some Kind of Wonderful,' the hosts of the Surely You Can't Be Serious Podcast dissect the casting, character dynamics, and thematic underpinnings of both films. They explore the controversial decision to darken Eric Stoltz’s red hair for the role of Keith, the complex chemistry between the leads, and the surprising behind-the-scenes stories—like Stoltz’s friendship with Cameron Crowe and Leah Thompson’s emotional recovery after the failure of Howard the Duck. The discussion highlights how both films use music as emotional glue, with particular praise for the iconic 'If You Leave' by Orchestral Manoeuvres in the Dark, which was hastily written after John Hughes changed the film’s ending. The hosts debate the plausibility of the endings, with differing opinions on whether Blaine’s apology in 'Pretty in Pink' is sufficient and whether the more realistic, understated romance in 'Some Kind of Wonderful' better serves its narrative. Ultimately, the episode balances nostalgic affection with critical analysis, revealing how both films, despite their flaws, remain culturally resonant. The hosts also unpack the symbolic weight of the prom dress in 'Pretty in Pink,' debating its design and significance—particularly its role as a fusion of two identities—while acknowledging its unflattering fit and Molly Ringwald’s personal dislike of it. They reflect on the gender dynamics, the portrayal of toxic masculinity through characters like Steph and Hardy, and the subtle but powerful performances that elevate both films. With a mix of humor, insight, and heartfelt nostalgia, the episode culminates in a passionate, three-way vote: Jill leans toward 'Pretty in Pink' for its emotional power and music, Jason favors 'Some Kind of Wonderful' for its stronger story and dialogue, and Jay ultimately chooses 'Pretty in Pink' after experiencing it anew in a theater with a diverse audience. The episode closes with a preview of next week’s track-by-track breakdown of 1980s power ballads.