‘The Sure Thing’ With Bill Simmons and Chris Ryan

December 18, 2025·1 hr 13 min·6 clips

Rob Reiner's son allegedly murdered him, but his legacy includes directing six Rewatchables classics and funding Seinfeld.

The cold open is pure Ringer housekeeping. A sponsor-style setup almost instantly becomes the host admitting he watched The Watch in bed while his wife played Block Blast nearby. Chris takes the teasing cleanly. The host likes the chemistry with Andy Greenwald, enjoys the Kaya jokes, then still asks for less pre-list buildup and tighter timestamp discipline. That is the rhythm: promo, compliment, roast, and real note, all stacked together before Craig Horlbeck gets dragged into the room. The movie talk settles in fast. The best stretch centers on the football-on-the-quad scene, with the panel treating it as both a real set piece and a personal memory button. They love the announcing. The male lead keeps up his Pat Summerall routine while running routes, grabbing interceptions, and glancing toward Allison without really talking to her. Someone calls him Ed Reed, which gets the joke exactly right. The scene plays teen-movie romance through absurdly committed athletic swagger. Allison is not background in the exchange. The panel notices her intensity, her back-and-forth energy, and the way the football scene keeps delaying any real connection until the pool beat. Then Craig gets grilled. His 2-on-2 football past leads into beach sports, flag football, blitz counts, stop-and-go routes, and the tiny rules movies somehow make feel familiar. The host folds that into childhood. As an only child, he says college came from visits with relatives and movies like this, where rooms had mountains of beer bottles and Friday night called from a window. The ending tightens into shelf talk. Stand By Me, One Crazy Summer, Risky Business, Cusack, and Reiner all go through the usual Rewatchables ranking machine. Craig sounds newly won over, putting this beside Risky Business as a favorite teen movie he had not seen before. The last beat is practical and wistful: can someone pay for the music so the movie can stream again? Then it gets filed as the lost Rob Reiner, and the quick goodbyes land.

As heard by us

A loose, affectionate Rewatchables trip through The Sure Thing, campus-movie mythology, and Rob Reiner's hard-to-stream comedy.

Bill Simmons, Chris Ryan, and Craig Horlbeck revisit The Sure Thing as a fondly remembered Rob Reiner teen comedy that still works through its character details: Cusack's loose, slightly chaotic charm, Allison's intense overachiever energy, and the easy back-and-forth that turns…

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Why you'd press play

The Rewatchables crew makes a case for a Rob Reiner teen movie you probably can't stream.

Read the full recommendation in PlayNext →

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