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The Rewatchables ·

When Harry Met Sally...

year 1989decade 80sdirector Rob Reinergenre Comedygenre Romance
host Bill Simmonshost Juliet Litmanhost Amanda Dobbins
All 18 categories

Most Rewatchable Scene · 20:47

Split: the first diner conversation

Bill Simmons: The 1977 car ride, grape spitting, diner order, Sheldon discussion, days-of-the-week underwear, and last-page habit are nominated as an opening cluster.

Bill Simmons: The 1982 airplane scene is nominated for the airport rule, white-man’s overbite, and debate over post-sex affection.

The film

When Harry Met Sally... (1989)

Directed by Rob Reiner · Comedy

95 minutes

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Cast

Selected cast credits · Film reference

Billy Crystal Harry Burns
Meg Ryan Sally Albright
Michelle Nicastro Amanda Reese
Kevin Rooney Ira Stone
Harley Kozak Helen Hillson
Estelle Reiner female customer

Everything from the episode

In the order the hosts got to it. Open a row for the discussion.

20:47

Most Rewatchable Scene

Split: the first diner conversation; Temple of Dendur; the wagon-wheel coffee-table breakdown

Split: the first diner conversation; Temple of Dendur; the wagon-wheel coffee-table breakdown

In the discussion (11)
Approx. transcript time · 00:20:47Read transcript
  • The 1977 car ride, grape spitting, diner order, Sheldon discussion, days-of-the-week underwear, and last-page habit are nominated as an opening cluster. — Bill Simmons
  • The 1982 airplane scene is nominated for the airport rule, white-man’s overbite, and debate over post-sex affection. — Bill Simmons
  • Carrie Fisher’s first lunch and Bruno Kirby’s batting-cage/baseball introduction are nominated together. — Bill Simmons
  • The Temple of Dendur “pecan pie” conversation is nominated for its photography, playfulness, and submerged romantic tension; one participant selects it.
  • The failed double date and the cab aftermath are nominated. — Bill Simmons
  • The Sharper Image “Surrey with the Fringe on Top” scene is nominated.
  • Harry’s “wagon-wheel coffee table” breakup rant is nominated and becomes one participant’s final choice.
  • The split-screen calls after Harry and Sally sleep together are nominated, with the difficult 61-take production story included. — Bill Simmons
  • The New Year’s Eve ending is admitted despite reservations discussed later.
  • The Katz’s Delicatessen fake-orgasm scene is recognized as iconic but rejected as overlong and less rewatchable.
  • The first diner scene receives one final preference for setting the film’s tone through a dense run of jokes.
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36:31

What’s Aged the Best?

Nora Ephron’s script, the 96-minute structure, friends-to-lovers premise, soundtrack, sexual candor, supporting frien...

Nora Ephron’s script, the 96-minute structure, friends-to-lovers premise, soundtrack, sexual candor, supporting friendships, old-movie references, and memorable micro-phrases

In the discussion (11)
Approx. transcript time · 00:36:31Read transcript
  • The screenplay and Ephron’s voice remain clean, influential, and highly readable. — Bill Simmons
  • The 96-minute runtime wastes no scene and avoids modern padding, contrived villains, and overloaded will-they/won’t-they plotting. — Bill Simmons
  • Friends realizing mutual love remains a powerful movie and real-life template. — Bill Simmons
  • Harry Connick Jr.’s classic-song soundtrack avoids the dating effect of period pop choices. — Bill Simmons
  • New York restaurants, Sally’s changing hair before the perm, her intricate ordering, and the Knicks drought jokes remain vivid. — Bill Simmons
  • Carrie Fisher’s “Joe’s available,” Jimmy Breslin, and the warning about sleeping with a friend remain sharply observed. — Bill Simmons
  • The movie’s frank treatment of sex, different expectations, and Harry’s absolutist friendship theory remains productive and mostly nonoffensive. — Bill Simmons
  • Nora Ephron is treated as irreplaceable and New York in autumn as permanently beautiful. — Bill Simmons
  • References to Casablanca and older romantic comedies teach viewers to rewatch and argue about movies. — Bill Simmons
  • The fake-orgasm scene helped make discussion of women’s sexual experience more open, and “he’s never going to leave her” remains practical relationship advice. — Amanda Dobbins
  • The Pictionary arrows and phrases such as “baby fish mouth” show how small jokes became durable shared language. — Bill Simmons
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47:25

What’s Aged the Worst?

The overexposed fake-orgasm scene, Meg Ryan’s perm and final-scene acting, dated aerobics and retail references, Bill...

The overexposed fake-orgasm scene, Meg Ryan’s perm and final-scene acting, dated aerobics and retail references, Billy Crystal’s age makeup, couple conformity, and lack of diversity

In the discussion (9)
Approx. transcript time · 00:47:25Read transcript
  • The fake-orgasm scene has lost surprise through repetition and now feels long, though its final line remains iconic. — Bill Simmons
  • Meg Ryan’s crying-scene perm is called an exceptionally bad haircut. — Bill Simmons
  • The heavily clothed aerobics or tap class feels unmistakably 1989. — Bill Simmons
  • Teenagers may no longer understand the Casablanca references even though the film itself has aged well. — Bill Simmons
  • The Sharper Image store and Theodore Roosevelt shooting reference require lost period knowledge.
  • Jess’s wedding speech is called mean by some panelists because it jokes that neither bride nor groom was attractive to their friends. — Bill Simmons
  • Meg Ryan’s repeated “I hate you” response in the climax is criticized as weak acting against Crystal’s strong speech.
  • Billy Crystal’s college hairpiece and aging treatment make him look older in 1977 than in 1989.
  • The story treats heterosexual coupledom as the only satisfying outcome and contains no visible gay or Black characters. — Amanda Dobbins
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57:51

The Dion Waiters Award for Best Heat Check Performance

Carrie Fisher

Carrie Fisher

In the discussion (2)
Approx. transcript time · 00:57:51Read transcript
  • Fisher’s Rolodex selfishness, repeated “You’re right, I know you’re right,” and emotional economy make five scenes feel career-defining.
  • The panel compares her favorably with later rom-com best friends and argues that Ephron’s friends are people rather than one-note assistants.
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1:01:03

Is There a Better Title for This Movie?

The released title

The released title

In the discussion (1)
Approx. transcript time · 01:01:03Read transcript
  • The panel ultimately prefers the specificity and memorability of “When Harry Met Sally.” — Bill Simmons
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1:05:36

Apex Mountain

Rob Reiner: qualified yes

Rob Reiner: qualified yes

In the discussion (4)
Approx. transcript time · 01:05:36Read transcript
  • Billy Crystal is rejected because City Slickers and his Oscar-hosting run take him higher. — Bill Simmons
  • Meg Ryan is rejected because later signature movies and an uneven filmography complicate the case. — Bill Simmons
  • Rob Reiner is proposed and partly accepted, though Misery and Castle Rock/Seinfeld success make a later peak plausible. — Bill Simmons
  • New York as a pop-culture setting is proposed and rejected in favor of the 1970s. — Bill Simmons
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1:07:25

The Joey Pants “That Guy” Award

Bruno Kirby

Bruno Kirby

In the discussion (1)
Approx. transcript time · 01:07:25Read transcript
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1:07:53

The Ruffalo / Hanna / Rubinek / Partridge Overacting Award

Meg Ryan

Meg Ryan

In the discussion (2)
Approx. transcript time · 01:07:53Read transcript
  • Ryan’s crying, tissue-dropping, and rapid tonal shifts are judged too broad and messy.
  • The panel debates whether several uninhibited moments fit the otherwise controlled “Miss Hospital Corners” characterization.
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1:22:45

Sequel, Prequel, Limited Series, or All-Black Remake

No present-day ten-episode remake; a period version or carefully written late-life sequel remains imaginable

No present-day ten-episode remake; a period version or carefully written late-life sequel remains imaginable

In the discussion (5)
Approx. transcript time · 01:22:45Read transcript
  • A present-day series built around direct messages and texting is judged inert. — Bill Simmons
  • A 1990s period treatment or two people forced together abroad is proposed as the only workable long-form remake. — Bill Simmons
  • A sequel could make Harry and Sally an older interview couple, explore their 35th anniversary, or center their adult children, but the panel fears an unwanted reboot. — Bill Simmons
  • Nancy Meyers, Meg Ryan as screenwriter, political-pundit Harry, and a Brentwood/Palisades relocation are proposed and repeatedly challenged because New York is essential.
  • A divorce-and-reunion sequel is rejected because the characters already resolved their avoidable mistakes. — Bill Simmons
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1:26:52

Who Won the Movie?

Disputed: Billy Crystal and Nora Ephron

Disputed: Billy Crystal and Nora Ephron

In the discussion (5)
Approx. transcript time · 01:26:52Read transcript
  • One participant chooses Billy Crystal for the final speech and the comic material that makes the film distinct. — Juliet Litman
  • Another leans Crystal because no other actor could sell the part, while resisting separating him from Meg Ryan. — Bill Simmons
  • One participant explicitly chooses Nora Ephron for establishing her later run and the modern rom-com form. — Bill Simmons
  • A second explicit choice moves to Ephron because the script could support other compatible lead pairs.
  • The discussion wavers back toward Crystal; one view is that the movie does not work without this particular pairing, so the chemistry is the real winner. — Amanda Dobbins
Podcast choices
Speaker not identified
Billy Crystal
Speaker not identified
Nora Ephron
Speaker not identified
Nora Ephron
Speaker not identified
Billy Crystal
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