The Rewatchables ‘The Sure Thing’ With Bill Simmons and Chris Ryan
11 snips
Dec 18, 2025 In this lively discussion, Craig Horlbeck, a producer at The Ringer and a regular contributor, joins Bill Simmons and Chris Ryan to celebrate Rob Reiner’s classic, ‘The Sure Thing.’ They explore Reiner’s genius in casting, particularly the youthful John Cusack, and how he masterfully blends humor with heartfelt moments. Craig shares his fresh, enthusiastic insights after watching the film for the first time, and the trio deep dives into standout scenes, the memorable '80s soundtrack, and the film’s legacy among iconic teen movies.
AI Snips
Chapters
Transcript
Episode notes
Director's Eye For Talent
- Rob Reiner excelled at spotting and elevating talent across different career phases.
- His movies succeed because he pairs actors and moments to maximize emotional and comic payoff.
Balancing Humor With Emotional Stakes
- Reiner balanced comedy and seriousness to make scenes feel emotionally truthful.
- He used emotional differences between characters to create obstacles that resolve satisfyingly.
New Fan Declares Cusack Breakout
- Craig Horlbeck admitted he'd never heard of The Sure Thing and called it an immediate favorite.
- He praised John Cusack's breakout, saying Cusack carried nearly every shot in the film.