The Rewatchables

‘The Sure Thing’ With Bill Simmons and Chris Ryan

December 18, 2025

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  • The hosts dedicated this special episode of *The Rewatchables* to Rob Reiner's film *The Sure Thing* as an immediate tribute following his tragic passing. 
  • The discussion highlighted Rob Reiner's exceptional career, characterized by an uncanny eye for talent across his acting, directing, and producing roles (e.g., *Spinal Tap*, *When Harry Met Sally*, funding *Seinfeld*). 
  • Both hosts, especially the first-time viewer Craig, lauded *The Sure Thing* as an underrated, classic 80s screwball comedy that elevates the 'opposites attract road trip' genre with genuine heart and humor. 
  • The hosts debate the long-term viability of Gibb and Allison's relationship, predicting they likely break up during college due to Gibb's recurring identity crisis. 
  • The speakers establish a definitive Mount Rushmore of 1980s teen movies, placing *Risky Business* and *The Sure Thing* at the top, followed by *The Breakfast Club* and *Ferris Bueller's Day Off*, while *The Karate Kid* is categorized as a sports movie. 
  • Daphne Zuniga's performance in *The Sure Thing* prompts a discussion about her potential career trajectory, suggesting she could have replaced Ally Sheedy in several iconic 'Brat Pack' roles. 

Segments

Tribute to Rob Reiner
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(00:03:07)
  • Key Takeaway: The Rewatchables episode was expedited as an emergency tribute to director Rob Reiner following his recent passing.
  • Summary: The hosts felt compelled to cover a Rob Reiner film immediately after his death, noting this was the seventh Reiner movie they have covered, placing him third among directors featured on the podcast. Reiner maintained three distinct, successful careers as a supporting actor, a director with an elite 15-year run, and as the founder of Castle Rock, which backed Seinfeld. The film The Sure Thing was chosen specifically to honor his contribution to entertainment.
Reiner’s Talent Eye
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(00:05:42)
  • Key Takeaway: Rob Reiner possessed a unique gift for identifying and maximizing talent, evident in his casting choices across multiple acclaimed films.
  • Summary: Reiner demonstrated a great eye for talent, exemplified by catching Tom Cruise at his apex in Few Good Men and convincing Jack Nicholson to take the role. He also championed emerging talent, such as casting Christopher Guest early in This Is Spinal Tap and identifying Robin Wright for The Princess Bride. Many actors, including Kevin Bacon and Noah Wyle, have shared powerful remembrances highlighting Reiner’s supportive nature on set.
Reiner’s Directing Style
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(00:09:41)
  • Key Takeaway: Reiner’s directorial skill lay in balancing serious, dire straits with hilarity, seeing the totality of the human experience in his stories.
  • Summary: Reiner excelled at making funny scenarios feel serious and serious scenarios contain humor, a balance also seen in Stand By Me. He was adept at fostering on-set relationships, which translated to believable chemistry on screen, making his films highly rewatchable. A key directorial philosophy noted was that emotional differences create the obstacles, which he then resolved satisfyingly within the two-hour runtime.
Cusack’s Impact and Film Context
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(00:11:03)
  • Key Takeaway: John Cusack’s performance in The Sure Thing cemented his status as a North Star for the hosts during their formative years, alongside films like Say Anything and High Fidelity.
  • Summary: The hosts realized they had underrated John Cusack’s impact, noting his central role in their imaginations from age 10 to 30. The Sure Thing is cited as a screwball comedy predecessor to modern rom-coms, similar in structure to When Harry Met Sally, which Reiner essentially created the modern version of. The film’s availability issues are speculated to be due to soundtrack licensing, as it was only available on YouTube at the time of recording.
Craig’s First Viewing Reaction
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(00:15:38)
  • Key Takeaway: Craig, watching The Sure Thing for the first time, immediately rated it a 10/10 and placed it among his favorite Rewatchables of the year.
  • Summary: Craig found the movie incredibly funny, heartfelt, and well-written, noting that Gibb’s character evolves from being perceived as just funny to someone putting on airs because he doesn’t know who he is. The film is compared favorably to Risky Business but is described as more grounded and human. The movie’s short runtime of about 90 minutes was also praised.
Film’s Genre Elevation
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(00:25:02)
  • Key Takeaway: The film is argued to have ended the era of sleazy 80s teen sex comedies like Porky’s by elevating the genre with respect and thought for the characters’ love lives.
  • Summary: Roger Ebert praised The Sure Thing as a small miracle because it believed sex should be accompanied by respect and love, contrasting it with the sleazy teen movies of the time. The marketing made it seem like a raunchy comedy, but it is closer to the relationship focus of When Harry Met Sally. The movie is considered a classic because it modernized the ‘opposites attract on the road’ trope.
Most Rewatchable Scenes
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(00:27:40)
  • Key Takeaway: The opening credits, featuring Rod Stewart’s ‘Infatuation,’ are highlighted as a lost art form that perfectly sets the vibe for the movie.
  • Summary: The first classroom scene establishing Gibb’s carefree nature versus Allison’s intensity was noted as a strong setup moment. The two-on-two flag football scene on the quad was celebrated for its authentic 80s college feel, including the ‘stop and go’ route. The final scene where the professor reads Allison’s essay is considered an excellent payoff, demonstrating Reiner’s ability to nail a moment.
1985 Cultural Artifacts
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(00:35:18)
  • Key Takeaway: The reliance on writing detailed letters, using cordless phones, and the prevalence of specific 80s teen tropes like space talk and certain posters define the film’s era.
  • Summary: Writing long letters to friends and the excitement of checking the mailbox are cited as common 1985 activities that have aged poorly due to modern communication. The line ‘I’m talking to you cordless’ is an iconic marker of the time period before ubiquitous cell phones. The film also features the 80s trope of using stars and outer space as a way to show a character’s depth beyond just seeking sex.
Casting and Character Details
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(00:40:37)
  • Key Takeaway: The film’s supporting cast, including Tim Robbins and Anthony Edwards, showcased excellent early career performances that Reiner expertly utilized.
  • Summary: The stuffy boyfriend, Nick (played by Tim Robbins), is praised for his perfectly written character details, such as having flannel sheets and offering tea choices. Anthony Edwards’ character, who is shown hosting a party with many girls, highlights the unrealistic portrayal of college life in Southern California versus the Northeast. The cinematographer, Robert Elswik, who also shot There Will Be Blood, is noted as another example of Reiner’s eye for top-tier collaborators.
Hottest Take and Relationship Longevity
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(00:50:16)
  • Key Takeaway: The hottest take is that Gibb and Allison met too early in their freshman year of college for their relationship to survive the inevitable personal changes of the next four years.
  • Summary: The hosts debated whether Gibb and Allison would remain a couple, with one arguing that Gibb’s inevitable post-high school identity crisis would cause him to break up with her. The idea of traveling 3,000 miles to meet someone for a hookup is cited as something that aged the worst due to modern dating apps like Bumble and Hinge. The character of Butch’s girlfriend is identified as the weakest link, feeling underdeveloped despite the film’s overall strong characterizations.
Gibb and Allison’s Future
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(00:51:15)
  • Key Takeaway: The hosts predict Gibb and Allison will not be a ‘forever couple,’ anticipating Gibb will repeat his high school crisis of needing to be independent.
  • Summary: The speakers doubt Gibb and Allison will last past college, speculating Gibb will experience a crisis similar to his high school one, feeling he must pursue other things before settling down. They also confirm Lance is out of the picture, having married a biologist. Gibb is predicted to win an intramural football championship, injuring his hand in the process.
80s Teen Movie Rankings
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(00:52:40)
  • Key Takeaway: Risky Business and The Sure Thing are ranked as the top two 80s teen movies featuring teen protagonists, with The Karate Kid being excluded from the top four.
  • Summary: The consensus places Risky Business and The Sure Thing as the top two 80s teen movies, followed by The Breakfast Club at third and Ferris Bueller’s Day Off at fourth. The Karate Kid is moved to the sports movie category, removing it from the primary teen movie ranking. This final Mount Rushmore is Risky Business, The Sure Thing, The Breakfast Club, and Ferris Bueller’s Day Off.
Casting What-Ifs and Zuniga
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(00:53:28)
  • Key Takeaway: Daphne Zuniga is argued to have been a superior choice for roles held by Ally Sheedy, potentially improving films like The Breakfast Club and St. Elmo’s Fire.
  • Summary: Anthony Edwards was considered for the lead role of Gibb before John Cusack secured it, and Robin Wright auditioned for Allison but was deemed too beautiful for the role to work. A ‘Hottest Take Award’ is established, and the hosts argue Zuniga should have been part of the Brat Pack, suggesting she could have replaced Ally Sheedy in multiple films. The discussion briefly touches on Demi Moore’s role in One Crazy Summer mirroring Zuniga’s type.
Best That Guy Awards
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(00:54:08)
  • Key Takeaway: Larry Hankin, who played the trucker, is recognized for his extensive career, including an appearance as Kramer’s alter ego in a Seinfeld episode.
  • Summary: Larry Hankin, the trucker, is awarded the ‘Best That Guy Award’ for his long career, including playing a cranky neighbor who dies in an unknown show and appearing in the Seinfeld episode where the main cast plays themselves in a TV show about the sitcom. Carmen Filipi is noted for being the bus station bum in St. Elmo’s Fire and the preacher in Halloween 4.
Deion Waiters Award Discussion
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(00:57:21)
  • Key Takeaway: The hosts resist renaming the ‘Deion Waiters Award’ to the ‘Bill Paxton Award,’ asserting the current name must remain due to its established history on the podcast.
  • Summary: Multiple listeners suggested renaming the ‘Deion Waiters Award’ to the ‘Bill Paxton Award,’ but the hosts refuse, stating Deion Waiters has been associated with the award for ten years. They joke about who is less remembered now: Deion Waiters or the show We Own This City. Tim Robbins is ranked highest among the potential candidates for the award.
Road Trip Movie Comparisons
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(01:03:00)
  • Key Takeaway: The scene where Gibb shotgunns a beer is considered an integral and well-executed moment in road trip movie history, surpassing even Animal House.
  • Summary: The hosts compare The Sure Thing to Midnight Run and Green Book as a road trip movie, concluding that the shotgunning beer scene is highly memorable. They praise how Daphne Zuniga’s character performs the shotgun in front of her boyfriend, which is noted as a funny moment. The best double feature pairing for The Sure Thing is suggested to be Stand By Me.
Ending Resonance and PJs
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(01:06:16)
  • Key Takeaway: The abrupt ending of The Sure Thing, cutting immediately to the kiss on the roof, is criticized for lacking the necessary follow-up dialogue after such a long build-up.
  • Summary: The 92-minute runtime is cited as a reason for the abrupt ending, suggesting a couple more minutes of dialogue after the resolution on the roof would have improved the resonance. Gibb’s bizarre, translucent pajamas and thin sweatpants worn on the trip are highlighted as a strange wardrobe choice for a character who also packs a perfectly ironed suit.