‘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
Categories
Great Shot Gordo Award
Bill SimmonsThe professor reading the short essay scene - 'Does God exist? Who invented liquid soap and why?' And then the answer was no.▶ 32:40
Chris RyanThe dive bar scene with the fat drunk guy and the waitress where he keeps giving her random facts▶ 34:25
What's Aged the Best
Chris RyanThe vision of 1980s college life - the classes, fashions, Allison's structured day schedule, Friday night partying▶ 42:20
Best Quote
Chris RyanExchange where Cusack says he plays football for Grambling, friend says 'I thought Grambling was all black,' and Cusack responds 'So what?'▶ 45:02
Butch's Girlfriend Award
Bill SimmonsThe Sheridan character (the sure thing) - they don't do a good enough job with her▶ 45:37
Chris RyanThe casting/presentation of both Nicolette Sheridan and Jason (the boyfriend) as unrealistic caricatures rather than relatable humans▶ 46:38
What's Aged the Worst
Chris RyanTraveling 3000 miles to get laid because there are apps now like Bumble, Hinge, and Tinder▶ 49:55
Probably Unanswerable Questions
Bill SimmonsWalter 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▶ 52:01
Chris RyanThey 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▶ 52:18
Casting What-Ifs
Bill SimmonsAnthony 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▶ 53:45
Chris RyanAnthony 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▶ 54:25
Apex Mountain
Bill SimmonsMidnight 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▶ 1:00:37
Hanks or Cruise
Bill SimmonsTom Hanks — Hanks - says this would have been a good Tom Hanks movie, mentions Cruise could have been the Anthony Edwards part instead▶ 1:04:30
Movies Referenced (32)
| Title (year) | Links | Mentions | Mentioned by | First |
|---|---|---|---|---|
| Risky Business (1983) | IMDb ↗Lb ↗ | 8 | Bill Simmons, Chris Ryan | ▶ 14:54 |
| Stand by Me (1986) | IMDb ↗Lb ↗ | 8 | Bill Simmons, Chris Ryan | ▶ 8:13 |
| Road Trip (2000) | IMDb ↗Lb ↗ | 6 | Chris Ryan, Bill Simmons | ▶ 9:44 |
| Say Anything (1989) | IMDb ↗Lb ↗ | 3 | Chris Ryan, Bill Simmons | ▶ 11:01 |
| Before Sunrise (1995) | IMDb ↗Lb ↗ | 2 | Chris Ryan | ▶ 16:11 |
| Green Book (2018) | IMDb ↗Lb ↗ | 2 | Chris Ryan, Bill Simmons | ▶ 1:03:40 |
| Halloween (1978) | IMDb ↗Lb ↗ | 2 | Chris Ryan | ▶ 40:25 |
| High Fidelity (2000) | IMDb ↗Lb ↗ | 2 | Bill Simmons, Chris Ryan | ▶ 10:49 |
| Misery (1990) | IMDb ↗Lb ↗ | 2 | Bill Simmons, Chris Ryan | ▶ 8:03 |
| Pump Up the Volume (1990) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 3:16 |
| Rushmore (1998) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 53:19 |
| The Beach (2000) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 29:47 |
Directors Referenced (7)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Rob Reiner | IMDb ↗Lb ↗ | 6 | Bill Simmons, Chris Ryan | This Is Spinal Tap, The Wolf of Wall Street | ▶ 3:27 |
| Sean Penn | IMDb ↗Lb ↗ | 5 | Bill Simmons, Chris Ryan | Mystic River, 21 Grams, Dead Man Walking | ▶ 1:37 |
| Hannah Storm | IMDb ↗Lb ↗ | 2 | Chris Ryan, Bill Simmons | Valentine's Day, Creed | ▶ 50:22 |
| Béla Tarr | IMDb ↗Lb ↗ | 1 | Chris Ryan | ▶ 35:12 | |
| Frank Capra | IMDb ↗Lb ↗ | 1 | Chris Ryan | It's a Wonderful Life, It Happened One Night | ▶ 21:48 |
| Paul Thomas Anderson | IMDb ↗Lb ↗ | 1 | Bill Simmons | Punch-Drunk Love, Licorice Pizza, There Will Be Blood | ▶ 49:21 |
| Tim Burton | IMDb ↗Lb ↗ | 1 | Chris Ryan | Edward Scissorhands | ▶ 56:30 |
Actors Referenced (50)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| John Cusack | IMDb ↗Lb ↗ | 25 | Bill Simmons, Chris Ryan | High Fidelity, 1408 | ▶ 9:07 |
| Daphne Zuniga | IMDb ↗Lb ↗ | 10 | Bill Simmons, Chris Ryan | Spaceballs | ▶ 19:32 |
| Anthony Edwards | IMDb ↗Lb ↗ | 8 | Bill Simmons, Chris Ryan | Top Gun, Zodiac | ▶ 23:46 |
| Tim Robbins | IMDb ↗Lb ↗ | 7 | Chris Ryan, Bill Simmons | Mystic River, The Player, Howard the Duck | ▶ 24:17 |
| Jerry Seinfeld | IMDb ↗Lb ↗ | 4 | Bill Simmons, Chris Ryan | ▶ 4:36 | |
| Robin Wright | IMDb ↗Lb ↗ | 4 | Bill Simmons, Chris Ryan | Forrest Gump, Unbreakable | ▶ 7:00 |
| Rod Stewart | IMDb ↗Lb ↗ | 4 | Bill Simmons, Chris Ryan | No Way Out | ▶ 27:56 |
| Bill Paxton | IMDb ↗Lb ↗ | 3 | Bill Simmons, Chris Ryan | Aliens, Apollo 13 | ▶ 58:06 |
| Billy Crystal | IMDb ↗Lb ↗ | 3 | Bill Simmons | City Slickers, When Harry Met Sally... | ▶ 8:39 |
| Castle Rock | IMDb ↗Lb ↗ | 3 | Bill Simmons, Chris Ryan | ▶ 4:19 | |
| Kevin Bacon | IMDb ↗Lb ↗ | 3 | Chris Ryan, Bill Simmons | Footloose, Hollow Man | ▶ 5:59 |
| Kid Cudi | IMDb ↗Lb ↗ | 3 | Bill Simmons | The Harder They Fall, Don't Look Up, Need for Speed | ▶ 23:12 |
Writers Referenced (5)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Roger Ebert | IMDb ↗Lb ↗ | 4 | Bill Simmons, Chris Ryan | ▶ 9:14 | |
| Stephen King | IMDb ↗Lb ↗ | 3 | Bill Simmons | ▶ 8:03 | |
| Andy Greenwald | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 0:56 | |
| Brian Koppelman | IMDb ↗Lb ↗ | 1 | Bill Simmons | Runaway Jury, Michael Clayton | ▶ 25:41 |
| Jonathan Roberts | IMDb ↗Lb ↗ | 1 | Bill Simmons | The Lion King | ▶ 24:30 |
Cinematographers Referenced (1)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Robert Bauer | IMDb ↗Lb ↗ | 1 | Bill Simmons | ▶ 59:38 |