Grays Almanac

Home/Episodes/The Sure Thing

‘The Sure Thing’ With Bill Simmons and Chris Ryan

December 18, 2025 · The Sure Thing (1985) · Comedy · Drama · Romance · 1:12:36 · ▶ Listen on Spotify

IMDb ↗Letterboxd ↗

Categories

Most Rewatchable Scene

Bill Simmons▶ 14:20the ending of this movie with the professor reading the story
Bill Simmons▶ 28:50Ran the candidate list without crowning one winner in-window: the Rod Stewart 'Infatuation' opening credits, the first classroom scene setting up Gibb and Allison, the quad football scene, the swimming-pool scene, getting kicked out of Tim Robbins' car, foiling the hitchhiker ('crazy slime ball'), the pouring-rain/credit-card scene, and the accidental cuddle scene
Chris Ryan▶ 29:07The 2-on-2 quad football scene with Cusack's Pat Summerall play-by-play — '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. This is such a funny fucking scene'

Bill's most memorable young-actor eighties movie performances

Unranked list · Bill Simmons · ▶ 17:46

  1. ·John Cusack in The Sure Thing▶ 17:46
  2. ·Matthew Broderick in Ferris Bueller's Day Off▶ 18:50
  3. ·Judd Nelson in The Breakfast Club▶ 18:55

Categories, continued

Stephen A. Smith Hottest Take Award

Bill Simmons▶ 25:07The Sure Thing ended the Porky's era — the movie that said 'we're done now' with raunchy teen sex comedies and elevated the genre ('this movie sells sex, but it doesn't give you any'); backed with Ebert's 'small miracle' review
Chris Ryan▶ 25:29Agreed and elaborated: one comic sex scene, otherwise chaste despite the raunchy marketing/poster — 'closer to if the road trip scene from When Harry Met Sally was the whole movie with 18-year-olds'

Great Shot Gordo Award

Bill Simmons▶ 32:40The professor reading the short essay scene - 'Does God exist? Who invented liquid soap and why?' And then the answer was no.
Chris Ryan▶ 34:25The dive bar scene with the fat drunk guy and the waitress where he keeps giving her random facts

What's Aged the Best

Bill Simmons▶ 42:58Young Cusack - knowing you're going to spend the next 40 years with this guy
Chris Ryan▶ 42:20The vision of 1980s college life - the classes, fashions, Allison's structured day schedule, Friday night partying

Best Quote

Chris Ryan▶ 45:02Exchange where Cusack says he plays football for Grambling, friend says 'I thought Grambling was all black,' and Cusack responds 'So what?'

Butch's Girlfriend Award

Bill Simmons▶ 45:37The Sheridan character (the sure thing) - they don't do a good enough job with her
Chris Ryan▶ 46:38The casting/presentation of both Nicolette Sheridan and Jason (the boyfriend) as unrealistic caricatures rather than relatable humans

What's Aged the Worst

Chris Ryan▶ 49:55Traveling 3000 miles to get laid because there are apps now like Bumble, Hinge, and Tinder

Probably Unanswerable Questions

Bill Simmons▶ 52:01Walter and Alison's relationship fails when he gets drunk one night, makes out with another girl, she never forgives him, and campus police have to intervene because he keeps showing up at her room
Chris Ryan▶ 52:18They make it through most of college until Walter has the same crisis as at the end of high school - he can't be with the same girl into his twenties and needs to go be himself

Casting What-Ifs

Bill Simmons▶ 53:45Anthony Edwards — Anthony Edwards almost got Cusack's lead role; Robin Wright auditioned for Nicolette Sheridan's part but casting her would have made the movie unrealistic since she's too beautiful to be believably single; Mare Winningham was up for Allison but Daphne Zuniga was better and should have replaced Ally Sheedy in all Brat Pack roles
Chris Ryan▶ 54:25Anthony Edwards — Agreed on Anthony Edwards for Gibb and Mare Winningham for Allison; noted Demi Moore played the Daphne Zuniga-type role in One Crazy Summer and wondered how big a career Zuniga could have had; suggested Tom Cruise or Rob Lowe could have been Lance

Apex Mountain

Bill Simmons▶ 1:00:37Midnight Run — No for Cusack, no for Daphne Zuniga (has Spaceballs next year), no for Anthony Edwards, no for road trip movies (says Midnight Run), no for hitchhiking, yes for shotgunning beers, no for Nicola Sheridan
Chris Ryan▶ 1:00:44Suggests Gibb's roommate's sexual position, no for road trip movies

Hanks or Cruise

Bill Simmons▶ 1:04:30Tom Hanks — Hanks - says this would have been a good Tom Hanks movie, mentions Cruise could have been the Anthony Edwards part instead

Just One Oscar

Bill Simmons▶ 1:10:27Rob Reiner — Reiner

Coach Finstock Life Lesson

Chris Ryan▶ 1:11:31Next time, just take the bus the whole way

Best Double Feature

Bill Simmons▶ 1:12:00Stand by Me — Stand By Me

Who Won the Movie

Bill Simmons▶ 1:12:07Rob Reiner — Rob Reiner (though acknowledges it's probably Cusack)
Chris Ryan▶ 1:12:13Rob Reiner — Agrees with Rob Reiner

Movies Referenced (27)

Risky Business (1983)

8 mentions · Bill Simmons, Chris Ryan▶ 14:54IMDb ↗Lb ↗

Stand by Me (1986)

8 mentions · Bill Simmons, Chris Ryan▶ 8:13IMDb ↗Lb ↗

Say Anything (1989)

3 mentions · Chris Ryan, Bill Simmons▶ 11:01IMDb ↗Lb ↗

Before Sunrise (1995)

2 mentions · Chris Ryan▶ 16:11IMDb ↗Lb ↗

Green Book (2018)

2 mentions · Chris Ryan, Bill Simmons▶ 1:03:40IMDb ↗Lb ↗

High Fidelity (2000)

2 mentions · Bill Simmons, Chris Ryan▶ 10:49IMDb ↗Lb ↗

Misery (1990)

2 mentions · Bill Simmons, Chris Ryan▶ 8:03IMDb ↗Lb ↗

Pump Up the Volume (1990)

2 mentions · Bill Simmons▶ 3:16IMDb ↗Lb ↗

Rushmore (1998)

2 mentions · Bill Simmons▶ 53:19IMDb ↗Lb ↗

A Few Good Men (1992)

1 mentions · Chris Ryan▶ 13:14IMDb ↗Lb ↗

Before Sunset (2004)

1 mentions · Chris Ryan▶ 17:07IMDb ↗Lb ↗

Better Off Dead (1985)

1 mentions · Chris Ryan▶ 11:01IMDb ↗Lb ↗

Directors Referenced (7)

Rob Reiner

8 mentions · Bill Simmons, Chris Ryan · Known for This Is Spinal Tap, The Wolf of Wall Street▶ 3:27IMDb ↗Lb ↗

Sean Penn

5 mentions · Bill Simmons, Chris Ryan · Known for Mystic River, 21 Grams, Dead Man Walking▶ 1:37IMDb ↗Lb ↗

Hannah Storm

2 mentions · Chris Ryan, Bill Simmons · Known for Valentine's Day, Creed▶ 50:22IMDb ↗Lb ↗

Béla Tarr

1 mentions · Chris Ryan▶ 35:12IMDb ↗Lb ↗

Frank Capra

1 mentions · Chris Ryan · Known for It's a Wonderful Life, It Happened One Night, You Can't Take It with You▶ 21:48IMDb ↗Lb ↗

Paul Thomas Anderson

1 mentions · Bill Simmons · Known for Punch-Drunk Love, Licorice Pizza, There Will Be Blood▶ 49:21IMDb ↗Lb ↗

Tim Burton

1 mentions · Chris Ryan · Known for Edward Scissorhands, Frankenweenie, Corpse Bride▶ 56:30IMDb ↗Lb ↗

Actors Referenced (49)

John Cusack

25 mentions · Bill Simmons, Chris Ryan · Known for Grosse Pointe Blank, High Fidelity, 1408▶ 9:07IMDb ↗Lb ↗

Daphne Zuniga

10 mentions · Bill Simmons, Chris Ryan · Known for Spaceballs▶ 19:32IMDb ↗Lb ↗

Anthony Edwards

8 mentions · Bill Simmons, Chris Ryan · Known for Top Gun, Zodiac▶ 23:46IMDb ↗Lb ↗

Tim Robbins

7 mentions · Chris Ryan, Bill Simmons · Known for Mystic River, The Player, Howard the Duck▶ 24:17IMDb ↗Lb ↗

Jerry Seinfeld

4 mentions · Bill Simmons, Chris Ryan · Known for Bee Movie▶ 4:36IMDb ↗Lb ↗

Robin Wright

4 mentions · Bill Simmons, Chris Ryan · Known for Forrest Gump, Beowulf, Unbreakable▶ 7:00IMDb ↗Lb ↗

Rod Stewart

4 mentions · Bill Simmons, Chris Ryan · Known for Innerspace, No Way Out▶ 27:56IMDb ↗Lb ↗

Bill Paxton

3 mentions · Bill Simmons, Chris Ryan · Known for Aliens, Apollo 13▶ 58:06IMDb ↗Lb ↗

Billy Crystal

3 mentions · Bill Simmons · Known for Forget Paris, City Slickers, When Harry Met Sally...▶ 8:39IMDb ↗Lb ↗

Castle Rock

3 mentions · Bill Simmons, Chris Ryan▶ 4:19IMDb ↗Lb ↗

Kevin Bacon

3 mentions · Chris Ryan, Bill Simmons · Known for Footloose, Hollow Man▶ 5:59IMDb ↗Lb ↗

Kid Cudi

3 mentions · Bill Simmons · Known for The Harder They Fall, Don't Look Up, Need for Speed▶ 23:12IMDb ↗Lb ↗

Writers Referenced (5)

Roger Ebert

4 mentions · Bill Simmons, Chris Ryan▶ 9:14IMDb ↗Lb ↗

Stephen King

3 mentions · Bill Simmons · Known for Maximum Overdrive, Creepshow▶ 8:03IMDb ↗Lb ↗

Andy Greenwald

2 mentions · Bill Simmons▶ 0:56IMDb ↗Lb ↗

Brian Koppelman

1 mentions · Bill Simmons · Known for Runaway Jury, Runner Runner, Michael Clayton▶ 25:41IMDb ↗Lb ↗

Jonathan Roberts

1 mentions · Bill Simmons · Known for The Lion King, James and the Giant Peach▶ 24:30IMDb ↗Lb ↗

Cinematographers Referenced (1)

Robert Bauer

1 mentions · Bill Simmons · Known for Weekend at Bernie's II▶ 59:38IMDb ↗Lb ↗