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THE REWATCHABLES · December 17, 2025

The Sure Thing

A 1985 comedy / romance / christmas movie directed by Rob Reiner—and decision no. 87 in the Hanks–Cruise tape.

ComedyRomanceChristmas1980sDirected by Rob Reiner
The Sure Thing1985MOVIE

ON THIS EPISODE

Podcast episode#426No. 437 overall
Movie year19851980s release
Tomatometer81%No. 59 of 128 tracked
Metacritic76View score
Roger Ebert—No review recorded
State of the raceHanks led by 143–42 · 2 ties

FROM THE CONVERSATION

What they said about the movie

The hosts praise The Sure Thing as a lost 80s classic and use it to celebrate Rob Reiner’s gift for casting, relationship dynamics, and mixing comedy with real emotion. They frame it as a smarter, less sleazy teen/road-trip movie that helped close out the Porky’s-era sex comedy wave.
Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

WHY IT WORKS

What made it rewatchable

  1. 01John Cusack’s performance is singled out as his most likable and a major reason to revisit the film. About 8 min
  2. 02The movie balances humor and sincerity through long scenes and emotional payoff. About 8 min
  3. 03Reiner’s directing style makes the characters feel like a real hangout and relationship movie. About 8 min
  4. 04The movie is tight, funny, and easy to rewatch in a short runtime. About 16 min
  5. 05The opening credits and Rod Stewart song immediately create a strong vibe. About 16 min

WHAT DID NOT WORK

Their main criticisms

  1. minorThe ending cuts off a little too abruptly after the rooftop kiss. About 56 min
  2. minorSome of the hitchhiking and trucker material feels dated by modern standards. About 48 min
  3. minorThe poster and marketing make the movie look like a more generic raunchy teen comedy than it is. About 40 min

SCENES THEY KEPT COMING BACK TO

Standout moments

Favorite

Opening credits and Rod Stewart song

The opening credits are praised for setting tone and energy immediately.

About 16 min
Favorite

First classroom scene

Introduces Gib as carefree and Alison as driven, establishing the central contrast.

About 16 min
Favorite

Football on the quad / campus football game

They enjoy the comic athletic energy and Gib’s announcer-style narration.

About 16 min
positive

Swimming pool / car-kicking sequence

A funny sequence that shows Cusack’s willingness to go for it and builds character dynamics.

About 16 min
Favorite

Tim Robbins car ride

The car sequence with show tunes, beer, and cheese balls is highlighted as a great comic stretch.

About 16 min
mixed

Hitchhiker/trucker scene

Funny in execution but dated and a little uncomfortable by modern standards.

About 48 min
Favorite

Professor reading Allison’s essay

Called one of the best parts of the movie and a satisfying emotional finish.

About 8 min
positive

Rooftop kiss ending

Strong romantic payoff, though some think it ends a beat too quickly.

About 56 min

WHERE THEY DISAGREED

The biggest debates

They partly agreed About 56 min

How well the ending resolves the romance

Craig Horlbeck

The ending is great but cuts off too fast; he wants a couple more minutes.

Bill Simmons

The abrupt finish works overall, though a tiny bit more runway would be fine.

No final agreement About 24 min

Whether Gib and Alison would last as a couple

Bill Simmons

They probably would not make it long-term; college and changing identities would split them.

Chris Ryan

They might last longer, but the relationship still faces big changes.

Craig Horlbeck

He thinks they make it for a while but not forever.

They partly agreed About 40 min

Best 80s teen movie ranking

Bill Simmons

He ranks Risky Business, The Sure Thing, Breakfast Club, and Ferris Bueller in a top group, with Karate Kid more of a sports movie.

Chris Ryan

He strongly agrees on The Sure Thing and Risky Business as the top two.

Craig Horlbeck

He mostly agrees after discussion and accepts Karate Kid as more of a sports movie.

11 People discussedActors, directors, writers, and producers
12 Conversation takesSpeakers shown only where the transcript identifies them
Bill SimmonsLoved it

The Sure Thing

Calls it one of the best 80s movies and a lost classic.

About 16 min
Bill SimmonsLoved it

Rob Reiner

Frames Reiner as a rare filmmaker whose whole career across acting, directing, and producing was meaningful and beloved.

Opening minutes
Bill SimmonsLoved it

John Cusack as Gib

Says this is the most likable Cusack has ever been and a career-defining turn.

About 8 min
Bill SimmonsLoved it

final essay-reading ending

Very enthusiastic about the professor reading Allison’s essay and the ending payoff.

About 8 min
Bill SimmonsMixed

Porky’s-style teen comedies

Argues this movie effectively ends the sleazier era of horny teen comedies by being smarter and more romantic.

About 40 min
Bill SimmonsLiked it

Daphne Zuniga

Thinks she should have had an even bigger 80s career and could have been in the Brat Pack.

About 16 min
Bill SimmonsLiked it

opening credits

Feels the opening credits and vibe-setting song are a lost art.

About 16 min
Chris RyanLoved it

The Sure Thing

Says he adored it and immediately ranks it among his favorites of the year for the show.

About 16 min
Chris RyanLoved it

John Cusack

Agrees Cusack is the most likable he has ever been and that the film showcases him best.

About 16 min
Chris RyanLoved it

classroom / essay reading scenes

Likes the long, slow, intimate scenes that build the relationship and payoff.

About 16 min
Chris RyanLoved it

Risky Business

Uses Risky Business as a benchmark and says The Sure Thing belongs in the same top tier of teen movies.

About 40 min
Chris RyanLoved it

Rob Reiner

Credits Reiner with understanding how to mix comedy, seriousness, and human behavior in the same story.

About 8 min
5 ThemesThe larger ideas in the discussion

Rob Reiner as talent spotter

The discussion repeatedly emphasizes Reiner’s ability to cast actors at the exact right point in their careers.

About 8 min

Relationships as the core of the film

They argue the movie works because Reiner understands chemistry, conflict, and emotional contrast between characters.

About 8 min

Smart version of the horny teen comedy

The film is presented as a more thoughtful alternative to the era’s sleazier college/sex comedies.

About 40 min

Coming-of-age uncertainty

They read Gib as a young man improvising identities and Alison as a serious achiever, with the movie tracking their self-discovery.

About 8 min

Long, lived-in scenes

They admire how Reiner lets scenes breathe, especially in classroom and road-trip stretches.

About 16 min
25 Facts and referencesProduction notes and other movies mentioned

Production note

The Sure Thing was not on streaming and was reportedly available on YouTube at the time of recording.

Opening minutes

Production note

Rob Reiner directed The Sure Thing as his second feature.

Opening minutes

Production note

John Cusack was very young during production and the story involved emancipation.

About 8 min

Production note

The film was shot for a $4.5 million budget and made $18.1 million.

About 24 min

Production note

Roger Ebert gave the film three and a half stars.

About 40 min

Mentioned with uncertainty

The soundtrack is mentioned as a possible reason the movie is not streaming.

Opening minutes · medium confidence

Production note

The movie includes a professor reading Allison’s essay aloud in class.

About 8 min

Production note

Cusack told Reiner he could shotgun beer, and the scene was added.

About 48 min

Production note

Larry Hankin plays the trucker/hitchhiker character.

About 56 min

Production note

The hosts joke that many of the movie’s shots were actually filmed in California even though it plays as a road movie.

About 48 min

The Watch

Used as a side conversation about Chris Ryan’s other podcast.

Opening minutes

Castle Rock

Discussed as Reiner’s production company and a key part of his industry legacy.

Opening minutes

Seinfeld

Cited as an example of Reiner’s producing impact through Castle Rock.

Opening minutes

Spinal Tap

Named as one of Reiner’s landmark projects and an early directing example.

About 8 min

The Princess Bride

Used to illustrate Reiner’s casting instincts and cross-generational appeal.

About 8 min

A Few Good Men

Mentioned as a strong example of Reiner’s talent for casting stars at peak moments.

About 8 min

Misery

Referenced as a top Stephen King adaptation and a great actor-driven thriller.

About 8 min

Stand By Me

Used repeatedly as another benchmark for Reiner’s emotional storytelling and ensemble casting.

About 8 min

When Harry Met Sally

Cited as a defining rom-com and a model for the genre.

About 8 min

It Happened One Night

Used as a classic screwball-road-romance influence on The Sure Thing.

About 24 min

Risky Business

Compared to The Sure Thing as a nearby 80s teen movie touchstone.

About 40 min

The Flamingo Kid

Mentioned as another smarter-than-expected movie in the teen/young-adult lane.

About 40 min

Before Sunrise

Craig compares the film’s long conversational passages to Linklater’s style.

About 16 min

The Breakfast Club

Discussed both as a contemporaneous teen movie and as a near-casting destination for Cusack.

About 16 min

Ferris Bueller's Day Off

Used as a top-tier teen-movie comparator in the rankings discussion.

About 40 min
10 Running jokes and short linesRecurring bits captured from the conversation

Fantasy football / punishment bets

The intro includes ongoing league jokes about punishments for losing fantasy football.

Opening minutes

Award-category renaming bit

They repeatedly riff on changing Rewatchables category names and award labels.

About 48 min

'Cordless' line riff

Bill and Chris repeatedly quote and reuse the film’s 'cordless' dialogue as a comic refrain.

About 32 min

Friday-beers / college-life fantasy

They riff on the movie’s fantasy of college life, especially beer and party culture.

About 16 min

Skinwalker tangent

A long off-topic gag about AI videos and skinwalkers becomes a comic side bit.

About 56 min

Bill Simmons

“The Sure Thing, a movie we've been waiting”
Opening minutes

Bill Simmons

“one of the best 80s movies”
About 16 min

Chris Ryan

“I absolutely loved it.”
About 16 min

Bill Simmons

“how would I go about”
About 8 min

Bill Simmons

“sex should be accompanied by respect and love”
About 40 min

MAKE IT A MOVIE NIGHT

Where to watch

UNITED STATES

Checking where The Sure Thing is available…

WHAT TO WATCH NEXT

Movies to watch before and after.

Three movies to watch before The Sure Thing, and three to watch next.

Finding six movies…Three to watch first and three to watch next.
Includes a Rewatchables episodePosters from TMDB.

ON THE MIC

2 voices made the call

Bill Simmons headshotBill Simmons125 tracked appearances · 56 H / 64 C / 5 ties
Chris Ryan headshotChris Ryan77 tracked appearances · 36 H / 38 C / 3 ties

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