‘The Sure Thing’ With Bill Simmons and Chris Ryan - The Rewatchables Recap

Podcast: The Rewatchables

Published: 2025-12-18

Duration: 1 hr 13 min

Guests: Chris Ryan

Summary

Bill Simmons and Chris Ryan revisit the 1985 film 'The Sure Thing', praising its blend of humor and serious themes. They discuss Rob Reiner's directorial prowess and the film's impact on the teen movie genre.

What Happened

Bill Simmons and Chris Ryan delve into 'The Sure Thing', a classic 1985 film directed by Rob Reiner, starring John Cusack and Daphne Zuniga. They praise Reiner's ability to balance humor with serious themes, highlighting his talent for long scenes and strong character relationships. The film is noted for its grounded portrayal of 1980s college life, contrasting with the raunchy teen comedies of its era. Simmons draws parallels between 'The Sure Thing' and Richard Linklater's 'Before Sunrise', focusing on character interaction and development.

Rob Reiner's influence on Hollywood is celebrated, with a nod to his three distinct careers: as an actor, a successful director, and a founder of Castle Rock Entertainment. Castle Rock played a crucial role in supporting young talent and funding iconic projects like 'Seinfeld'. The hosts discuss Reiner's knack for identifying and nurturing talent, which is evident in his casting choices for films such as 'When Harry Met Sally'.

John Cusack's performance in 'The Sure Thing' is lauded, with an interesting tidbit that he was emancipated at 17 to take on the role. The film's impact on the genre is significant, credited with ending the era of raunchy teen sex comedies like 'Porky's'. Roger Ebert praised 'The Sure Thing' as a 'small miracle', applauding its thoughtful portrayal of love and relationships.

The film's soundtrack, featuring artists like Rod Stewart and Huey Lewis, is speculated to be the reason it is not available on streaming services. The soundtrack's rights may be complicating its digital release. Despite this, the movie is celebrated as one of the best 1980s teen films, standing alongside 'Risky Business', 'Breakfast Club', and 'Ferris Bueller's Day Off'.

Memorable scenes include Gibb and Allison being kicked out of a car driven by Tim Robbins' character, Gary Cooper, and a scene where Gibb foils a potential hitchhiker rapist. These moments highlight the film's blend of humor and tension. The film also captures the essence of college life in the 1980s, from writing detailed letters to friends to the excitement of receiving mail.

Simmons and Ryan lament the film's relatively short 92-minute runtime, suggesting that a slightly longer cut might have provided better resolution. Despite this, they praise the pacing and the film's ability to immerse viewers in the college world before beginning the road trip. The episode concludes with reflections on how 'The Sure Thing' remains a standout in the teen movie genre, thanks to its authentic portrayal of young love and personal growth.

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