The Rewatchables: ‘The Sure Thing’ (Dec 18, 2025)

Podcast: The Rewatchables
Host(s): Bill Simmons, Rob Mahoney, Craig Horlbeck
Theme: A tribute to Rob Reiner, revisiting his 1985 cult road trip rom-com “The Sure Thing”—a lost classic that’s been out of streaming reach—unpacking its craftsmanship, performances, and lasting legacy.

Episode Overview

In this special episode, Bill Simmons, Rob Mahoney, and Craig Horlbeck revisit The Sure Thing—Rob Reiner's beloved, under-seen 1985 teen rom-com. Spurred by Reiner’s recent, tragic passing, the hosts pay homage to the director’s unique three-act career: sitcom star, A-list filmmaker, and tastemaker/producer (including his backing of Seinfeld). They dive deep into how Reiner’s sensibilities shaped The Sure Thing into more than just another ‘80s sex comedy and reflect on the movie’s scarcity in the streaming era. The panel mixes personal anecdotes, film history, and high-spirited banter, ultimately celebrating the movie’s enduring warmth, sharp writing, and Rob Reiner’s legacy as a champion of talent.

Remembering Rob Reiner: His Legacy and Versatility

[03:42–09:29]

• Reiner’s Tragic Passing: News of his death brings an urgent, emotional tone. Bill recounts Reiner’s unique Hollywood journey—from “Meathead” on All In The Family, to director, to Castle Rock founder and Seinfeld backer.

  • “He had these three different careers that were all pretty cool in their own ways.” (Bill Simmons, 04:13)

• Director’s Touch: Reiner’s “eye for talent,” especially in casting and capturing rising actors at the right moment, is repeatedly praised.

  • “He catches [Tom] Cruise at his apex… figures out the perfect Nicholson part… populates that movie with all these really good younger actors.” (Bill Simmons, 05:45)

• Sustained Excellence: The hosts note Reiner’s unprecedented, nearly flawless decade-plus directorial run, from Spinal Tap to A Few Good Men.

  • “He has five or six in a row to start off his career that are locks for any… I would rewatchable any of those with you.” (Rob Mahoney, 05:07)

• Best of Genre: They rattle off his genre-defining films, placing Spinal Tap as best music comedy, Princess Bride as the “best non-animated fairytale,” Few Good Men as best courtroom drama, Misery as top Stephen King adaptation, and When Harry Met Sally as the rom-com template.

What Makes ‘The Sure Thing’ (and Reiner) Special

[09:29–17:45]

• Elevating Material: The hosts argue Reiner could take potentially formulaic, even exploitative genres and inject authenticity, layered humor, and genuine stakes.

  • “He’s able to take funny scenarios and make them feel very serious or very serious scenarios and see the humor in them… that happens in The Sure Thing.” (Rob Mahoney, 09:36)

• Eye for Breakout Performances: Cusack’s career-making turn is highlighted as perhaps the “most likable he’s ever been.”

  • “To me, like Cusack in this movie—I had season tickets for the next 12 years just ‘cause of this movie.” (Bill Simmons, 10:45)
  • “…I’ve underrated the role that John Cusack played in my imagination over my entire life… from 10 to 30, this guy was basically like a sort of North Star.” (Rob Mahoney, 11:19)

• Director as Relationship Engineer: Reiner’s true gift is matching personalities on screen and fostering on-set chemistry to create relationships you want to spend time with.

  • “The rewatchability of his movies comes down to you just hanging out with the characters.” (Bill Simmons, 12:12)

• Long Scenes as Lost Art: The “long scene” is called out as a rare, effective device Reiner used to anchor emotion and humor, culminating in the professor reading the final essay.

  • “He also is really good at long scenes which I think is a lost art… I just love the ending of this movie so much with the professor reading the story.” (Bill Simmons, 14:01 & 14:40)

‘The Sure Thing’: Why It’s a Lost Classic

[14:40–25:29]

• Multi-genre Magic: The movie is a road trip, opposites-attract rom-com, “horny teens” 80s comedy, and college buddy flick—all wrapped up in 90 brisk minutes.

• Craig’s Fresh Take: As a first-timer, Craig raves:

  • “I absolutely loved it. This will immediately go on my favorites of the year for the rewatchables… a 10/10. … Cusack, I totally agree, the most likable he’s ever been… a little bit of, like, a ‘Before Sunrise’ element…” (Craig Horlbeck, 15:49)

• Reiner/Cusack Backstory: Details on how Reiner “had to have” a teen Cusack—even facilitating his emancipation so he could shoot—and Cusack losing The Breakfast Club role at the last minute to Judd Nelson.

  • “He has to file for emancipation… and Cusack’s still going.” (Bill Simmons, 09:29)
  • [18:10–18:52]: Details on Cusack’s near-miss with Breakfast Club, background cameos in Sixteen Candles, and break-out performance.

• Iconic Young Actors: The trio debates the great 80s youthful lead performances, settling on Cusack here, Broderick in Ferris Bueller, Judd Nelson in Breakfast Club, and Slater in Pump Up the Volume as the most memorable.

• Daphne Zuniga Appreciation: Her turn as Allison is praised—relatable, sharply drawn, and authentic.

Screwball Roots & Hollywood Connections

[21:17–23:19]

• Classic Comedy DNA: Rob highlights its screwball roots, calling out kinship with It Happened One Night and reflecting on Reiner’s Hollywood lineage and his “institutional knowledge”—both as Carl Reiner’s son and a student of Capra/Sturgis.

• Reiner's Reputation Shift: Bill recalls how “Meathead” (from All in the Family) had to reinvent himself into a respected director, with The Sure Thing as the pivotal moment.

The Supporting Cast and “Those Guys”

[23:51–25:08]

• Stacked Ensemble: Shout-outs to:** Anthony Edwards (pre-Top Gun), Tim Robbins (future collaboration mainstay), Nicolette Sheridan (future Desperate Housewives)**—plus a horde of “That Guy” character actors.

Elevation from Sex Comedy to Smart Rom-Com

[25:01–27:14]

• Porky’s Era Ender: Panel argues The Sure Thing ended the run of cheap "horny teen" comedies, bringing substance and nuance.

  • “I think… you could argue that this ended the Porky’s era. Like, this actual—this was the movie that was like, we’re done now.” (Bill Simmons, 25:29)

• Mismarketed: They note the film’s raunchy marketing and poster belie its genuinely heartfelt—and mostly chaste—core.

• Critical Praise: Roger Ebert’s review is highlighted:

  • “The love story is one of Hollywood’s missing genres… that’s why The Sure Thing is a small miracle. The film is so revolutionary: [It] believes sex should be accompanied by respect and love!” (Bill Simmons quoting Ebert, 25:56)

Most Rewatchable Scenes

[27:40–34:09]

They run through and debate the film’s most replayable sequences:

• Opening Credits with Rod Stewart’s “Infatuation” (28:02)

• First Classroom Scene: Sets up the carefree, lovable Gib and the intense Allison.

• Flag Football on the Quad: “If they wanted to do the first hour and a half of this movie being just football on the quad, I would have taken it.” (Rob Mahoney, 28:46)

• Gib & Allison Getting Kicked Out of Gary Cooper’s Car (Tim Robbins)

• Hitchhiker Scene: Gib foils a potential predator; comedic and tense.

• Downpour/Rain Trek

• Rom-Com ‘Cuddle Scene’: “Always works.” (Bill Simmons, 31:52)

• Truck Ride Confession

• Hawaiian Party

• The Professor’s Reading of Gib’s Essay: Clear consensus for best/payoff moment.

  • “It’s so f---ing good… I think this is one of the best 80s movies. I really do… it’s a road trip movie... a horny teenagers trying to get laid 80s movie. It’s weirdly kind of a fun college movie. And it all happens in an hour and 31 minutes or something.” (Bill Simmons, 14:40)

• Dive Bar Sequence: Cited for oddball realism and a standout “best-drunk-acting-ever-seen” by George Memmoli.

  • “The fat drunk guy at the bar, I think, is some of the best drunk acting I’ve ever seen.” (Craig Horlbeck, 33:40)

The Most ‘80s’ Details

[35:14–37:31]

• Handwritten Letters:
  • “Writing detailed letters to your friends from high school.” (Bill Simmons, 35:14)
• Bulletin Board Rideshares
• Culture Club Posters, Cordless Phones
• Sex Letters to Penthouse
• Dorm Room Decor (beer bottles, tennis girl poster)

What’s Aged the Best

[37:55–42:33]

• Soundtrack: Rod Stewart, John Waite, Eagles, The Cars, Wang Chung, Lionel Richie, Huey Lewis, etc.
• Romantic slow-burn structure
• Realness of college: “...made college seem just so great. Really seems like an awesome place.” (Bill Simmons, 38:38)
• Stuffy Boyfriend Trope, College Fashions, Dorm Life
• Early John Cusack energy and charisma

What’s Aged the Worst

[46:34–48:28]

• Cusack’s Valley Girl Impression (“not sure anyone would get that now” - Bill Simmons, 46:34)
• Hitchhiking as plot device
  • “And you know, we don’t do it because Netflix has been [airing] 45 true crime documentaries that end with a hitchhiker being murdered.” (Bill Simmons, 48:32)
• Traveling 3000 miles to get laid—apps have changed things
• Stars/stargazing as a “deep dude” trope
• Writing Workshops as unconvincing community

Performance, Casting, and What Ifs

[52:44–55:13]

• Casting What-ifs: Anthony Edwards nearly played Gib; Robin Wright auditioned for the “Sure Thing;” Zuniga could have slotted easily into Brat Pack films.
  • “Daphne Zuniga, I think, should have been in the Brat Pack… I just would rather have her than Ali Sheedy.” (Bill Simmons, 54:27)

Notable Quotes & Banter

• On Reiner’s Talent:

  • “He was able to see the totality of a human experience in any given scene and in any given story… Even something that could have just been a super horny, forgettable 80s comedy... is actually like a lost classic in a lot of ways.” (Rob Mahoney, 09:36–10:37)

• On Cusack’s Star Power:

  • “Cusack in this movie—I had season tickets for the next 12 years just 'cause of this movie.” (Bill Simmons, 11:04)

• On Outgrowing Teen Romance:

  • “Gib and Allison met just a hair too early to make it really work… Freshman year is tough, man.” (Rob Mahoney, 50:47)

Genre, Structure, and TV Potential

[67:57–68:43]

• The hosts toy with the idea of a Prestige TV adaptation, each “day” being an episode, but agree the film’s tight pace is part of what makes it work.

Awards and Categories Segment (Selected Highlights)

(All time stamps approx. / paraphrased where categories were riffed rapidly)

• Best That Guy: Larry Hankin as Trucker (55:28)
• Dion Waiters Award (scene-stealer): Vivica Lindfors as the professor (58:01)
• Apex Mountain: Not Cusack (probably Say Anything); probably Zuniga for Spaceballs.
• Best Needle Drop: “Penny Lover” during the slow dance.
• Weak Link: Underdeveloped “Sure Thing” character (Nicolette Sheridan).
• Unanswerable Question: How did Cusack’s character actually get in the rapist’s truck? Did Gib and Allison last through college?

Final Thoughts & Who Won the Movie?

• Who Won? The hosts agree: this one’s for Rob Reiner—“Let’s say Reiner for this one.” (Bill Simmons, 71:22)
• Closing Vibes: A hope that this pod will inspire streamers to license the soundtrack so a new generation can rediscover this “lost Rob Reiner classic.”

Memorable Moments & Meta-Banter

• Meta-pod moments: Debates on retiring the “Luke Wilson could have been Harrison Ford” hot take category (in favor of Rob Mahoney’s “Smells Like Teen Spirit Sucked” award) and imagining a March Madness bracket of the wildest Rewatchables takes. (50:08-50:47)
• On streaming negligence: “If Amazon got it or Netflix got it, it would immediately be, like, number one... because it’s so much fucking fun to watch.” (Bill Simmons, 17:46)
• On Reiner’s casting genius: “Once you did something with him, you were like a friend for life. And Hollywood’s not really that way. This guy was friends with every type of comedian and actor that we had.” (Bill Simmons, 12:16)

Conclusion

A heartfelt, funny, and enthusiastic salute to “The Sure Thing,” this episode celebrates Rob Reiner’s knack for timeless entertainment and finding humanity in unlikely places. The panel makes a persuasive case that “The Sure Thing” isn’t merely a hidden gem—it’s a generational all-timer that deserves a reappraisal and a proper streaming “re-release.”

TIMESTAMPS:

• [03:42–09:29]: Rob Reiner’s career and impact
• [14:40–25:29]: “The Sure Thing” as a road-trip/rom-com classic
• [27:40–34:09]: Most rewatchable scenes
• [35:14–37:31]: Most “1985” details
• [37:55–42:33]: What’s aged best
• [46:34–48:28]: What’s aged worst
• [52:44–55:13]: Casting what-ifs and Daphne Zuniga’s potential
• [58:01]: Scene-stealing/ Dion Waiters Award winner

“Rip, Rob Reiner. We’re gonna miss you.”
(Bill Simmons, 71:57)

For listeners and newcomers alike, this episode is a compelling case both for Reiner’s enduring influence and for rediscovering “The Sure Thing.”