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‘Sleepless in Seattle’ With Bill Simmons, Juliet Litman, and Amanda Dobbins

February 14, 2023 · Sleepless in Seattle (1993) · Comedy · Drama · Romance · 1:58:23

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Picking Nits

Amanda Dobbins▶ 9:08Bill Pullman's character being mature and adult-like in calling off the wedding when he sensed her heart wasn't in it
Bill Simmons▶ 9:15The character had an IQ of 74 and didn't understand what was happening, still thought they were getting married
Juliet Litman▶ 9:21He doesn't understand joy because he can't eat good food, so he's used to settling in life and willing to settle for a bad relationship

Stephen A. Smith Hottest Take Award

Bill Simmons▶ 9:39Tom Hanks and Meg Ryan are the GOATs of rom-coms and the movie works because they're so good they don't even need to be in scenes together

Most Rewatchable Scene

Bill Simmons▶ 27:24Mentions his wife's favorite scene (Meg Ryan trying on wedding dress in attic), discusses the radio call scene with Tom Hanks and Jonah, and mentions the tiramisu scene, but doesn't give one definitive personal pick

What's Aged the Worst

Amanda Dobbins▶ 40:55The clothes - while many 90s things have come back in style, these specific clothes have not
Bill Simmons▶ 41:21The clothes reflecting the height of AIDS fear era when everyone tried to hide behind their clothes and not look sexy
Juliet Litman▶ 41:00The fashion choices, particularly the drop waist dresses and excessive use of trench coats as an Annie Hall callback

What's Aged the Best

Amanda Dobbins▶ 44:10People talking as a format of content and parasocial relationships - you can tell a lot from someone's voice
Amanda Dobbins▶ 44:21The drinks, not dinner strategy for first dates - it's reliable and you can get out fast
Juliet Litman▶ 41:41Seattle and houseboats - the way they positioned Seattle with Pike Place Market and the water looks great and would be done the same way again
Juliet Litman▶ 42:45Internet stalking - it's never been more true and foreshadows the next 30 years of wanting to know as much as possible about someone you meet
Juliet Litman▶ 44:40Movie references like Fatal Attraction and Pride of the Yankees - the cultural references didn't age badly which is hard to pull off in a 1993 rom-com

Big Kahuna Burger Award

Amanda Dobbins▶ 48:13the lettuce and tomato sandwich scene
Bill Simmons▶ 48:26the lettuce and tomato sandwich scene when Annie Reed explains to her mom how they met
Juliet Litman▶ 48:01the sandwiches scene when Annie Reed's explaining to her mom how they met, because of the weird sandwich, lettuce and tomato

Den of Thieves Benihana Award

Bill Simmons▶ 48:59The Empire State Building

Great Shot Gordo Award

Amanda Dobbins▶ 50:03the helicopter shot where you see Jonah and then get all of New York when the camera goes backwards
Bill Simmons▶ 49:44the wide shot of the funeral with Chicago in the background
Juliet Litman▶ 49:54the framing of Jonah and Sam on the bench with them both on the phones

Butch's Girlfriend Award

Amanda Dobbins▶ 50:52Discusses Walter's deranged monologue while shopping for dishes at Tiffany and Gabby Hoffman's father but doesn't give a clear definitive pick
Bill Simmons▶ 50:18Walter just takes the broken engagement - when she canceled lunch with him on Wednesday and he doesn't understand he's not engaged anymore
Juliet Litman▶ 51:54Gabby Hoffman's parents, specifically her father who seems like a Seinfeld character

Overacting Award

Bill Simmons▶ 52:13Him (referring to someone who comes in smoking hot)

Probably Unanswerable Questions

Amanda Dobbins▶ 57:29No adult at any point asks the kid if he needs help or questions who he's meeting - like the taxi driver just accepts dropping off an 8-year-old alone
Bill Simmons▶ 55:43How can an 8-year-old kid order flights, land a plane, figure out taxi logistics, and navigate to the Empire State Building without any adult questioning where his parents are
Juliet Litman▶ 56:12The taxi logistics are outrageous, though she defends the flight booking since the girl is using travel agent equipment, not just calling airlines directly

Ron Burgundy Flute Award

Amanda Dobbins▶ 59:53The David Hyde Pierce scene
Bill Simmons▶ 59:33When the dead wife actually appears and does lines with him
Juliet Litman▶ 1:00:15When they call Dr. Marsha a second time, when Victoria comes over for dinner and Jonah calls again

Is There a Better Title?

Bill Simmons▶ 1:01:06No, the current title is perfect

Best Quote

Bill Simmons▶ 1:01:12You don't want to be in love, you want to be in love in a movie
Bill Simmons▶ 1:01:48It's easier to get killed by a terrorist than get married after the age of 40
Juliet Litman▶ 1:01:59Of what? Her first name could be Doctor

Apex Mountain

Juliet Litman▶ 1:02:31Rosie O'Donnell — Not Apex Mountain for Rosie O'Donnell, but acknowledges she's great in the movie

Casting What-Ifs

Amanda Dobbins▶ 1:12:31Meg Ryan — Notes Julia Roberts had personal issues during that period; emphasizes Meg Ryan's 'daffy' quality that Demi Moore and Robin Wright lack; stresses Meg Ryan's relatability is crucial for the role
Bill Simmons▶ 1:10:35Julia Roberts — Julia Roberts was offered Annie's role but turned it down; believes Demi Moore could have been interesting but Meg Ryan is perfect; Dennis Quaid was pushed by Meg Ryan for Hanks' role but overruled by Ephron
Juliet Litman▶ 1:11:51Julia Roberts — Agrees Julia Roberts was offered the role; thinks Demi Moore was too feisty/bad girl for Annie's character; notes Robin Wright and Demi Moore have different sex appeal than Meg Ryan's attainable quality

Half-Assed Internet Research

Bill Simmons▶ 1:30:22Several studios rejected the script, Efron was particular about his lines, the coward disappointed in Denver was voiced by Nora Ephron, Parker Posey was cut but ended up in You've Got Mail, and questioned whether Seinfeld ripped off the Soup Nazi from this movie
Juliet Litman▶ 1:30:54Parker Posey was cut out of the movie, the other story being pitched when Annie pitches hers is about the Soup Nazi that later shows up in Seinfeld, but thinks Seinfeld didn't rip it off - probably both encountered the same New York thing

Racehorse Name Award

Bill Simmons▶ 1:36:36Sleepless in Seattle
Juliet Litman▶ 1:36:41Hi and Goodbye

Is This Movie Better With

Amanda Dobbins▶ 1:42:02Kathryn Hahn — Catherine Hahn as best friend for Jennifer Lopez
Bill Simmons▶ 1:41:50Kathryn Hahn — Catherine Hahn in the Rita Wilson role for 2013 version, Sam Jackson as Hank's buddy instead of Rob Reiner
Juliet Litman▶ 1:41:56Zoë Chao — Zoe Chow in the Rosie role for 2023 version, likes Sam Jackson as buddy idea similar to Dave Chappelle in You've Got Mail

Best Double Feature

Amanda Dobbins▶ 1:46:51You've Got Mail — You've Got Mail as primary pick, with An Affair to Remember for a triple feature option
Bill Simmons▶ 1:47:11Joe Versus the Volcano — Joe vs. the Volcano
Juliet Litman▶ 1:46:45While You Were Sleeping

Coach Finstock Life Lesson

Amanda Dobbins▶ 1:53:28Discusses acceptable boundaries for pursuing someone - traveling across country is okay but don't stand outside someone's door; suggests staying within a certain radius
Bill Simmons▶ 1:53:03Stalking your future husband is okay if you're positive it's your future husband
Juliet Litman▶ 1:53:17Agrees with Bill's lesson but adds boundaries - going to great lengths to date someone is okay, but actual stalking is not

Who Won the Movie

Amanda Dobbins▶ 1:55:09Nora Ephron — Tom Hanks or Nora Ephron, leaning toward Nora Ephron for establishing her persona and getting credit for reinvigorating the rom-com genre
Bill Simmons▶ 1:55:07Meg Ryan

Movies Referenced (50)

You've Got Mail (1998)

23 mentions · Amanda Dobbins, Bill Simmons, Juliet Litman▶ 3:11IMDb ↗Lb ↗

Hook (1991)

6 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman▶ 1:09:43IMDb ↗Lb ↗

While You Were Sleeping (1995)

5 mentions · Amanda Dobbins, Juliet Litman, Bill Simmons▶ 20:23IMDb ↗Lb ↗

Forrest Gump (1994)

4 mentions · Bill Simmons▶ 8:11IMDb ↗Lb ↗

Project X (2012)

4 mentions · Bill Simmons▶ 31:34IMDb ↗Lb ↗

A League of Their Own (1992)

3 mentions · Amanda Dobbins, Bill Simmons▶ 20:27IMDb ↗Lb ↗

Fatal Attraction (1987)

3 mentions · Juliet Litman, Amanda Dobbins▶ 2:46IMDb ↗Lb ↗

Independence Day (1996)

3 mentions · Amanda Dobbins▶ 20:20IMDb ↗Lb ↗

Philadelphia (1993)

3 mentions · Bill Simmons, Amanda Dobbins▶ 16:08IMDb ↗Lb ↗

Pretty Woman (1990)

3 mentions · Amanda Dobbins, Bill Simmons▶ 11:58IMDb ↗Lb ↗

Apollo 13 (1995)

2 mentions · Bill Simmons▶ 16:23IMDb ↗Lb ↗

Dennis the Menace (1993)

2 mentions · Bill Simmons▶ 1:10:05IMDb ↗Lb ↗

Directors Referenced (8)

Ben Affleck

10 mentions · Amanda Dobbins, Bill Simmons, Juliet Litman · Known for Argo, Gone Girl, The Town▶ 50:11IMDb ↗Lb ↗

Rob Reiner

5 mentions · Bill Simmons, Amanda Dobbins · Known for This Is Spinal Tap, The Wolf of Wall Street▶ 14:06IMDb ↗Lb ↗

Bob Vila

2 mentions · Bill Simmons▶ 18:53IMDb ↗Lb ↗

Walt Frasier

2 mentions · Bill Simmons▶ 19:02IMDb ↗Lb ↗

Esther Perel

1 mentions · Amanda Dobbins▶ 30:53IMDb ↗Lb ↗

George Clooney

1 mentions · Bill Simmons · Known for The Ides of March, Michael Clayton▶ 10:52IMDb ↗Lb ↗

Penny Marshall

1 mentions · Bill Simmons · Known for Big, A League of Their Own▶ 1:34:43IMDb ↗Lb ↗

Steve Nash

1 mentions · Juliet Litman▶ 1:30:15IMDb ↗Lb ↗

Actors Referenced (83)

Meg Ryan

41 mentions · Bill Simmons, Juliet Litman, Amanda Dobbins · Known for When Harry Met Sally..., Sleepless in Seattle, You've Got Mail▶ 3:48IMDb ↗Lb ↗

Tom Hanks

39 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman · Known for Cast Away, Big, Forrest Gump▶ 5:01IMDb ↗Lb ↗

Bill Pullman

22 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman · Known for Independence Day, Spaceballs▶ 5:01IMDb ↗Lb ↗

Rosie O'Donnell

19 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman · Known for A League of Their Own, Sleepless in Seattle, Tarzan▶ 13:50IMDb ↗Lb ↗

Harry Connick Jr.

15 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman · Known for Hope Floats▶ 3:22IMDb ↗Lb ↗

Elando Baltimore

13 mentions · Juliet Litman, Bill Simmons, Amanda Dobbins▶ 43:20IMDb ↗Lb ↗

Empire of the Sun

11 mentions · Bill Simmons, Amanda Dobbins · Known for Sex Tape, Hall Pass▶ 48:59IMDb ↗Lb ↗

Julia Roberts

11 mentions · Bill Simmons, Amanda Dobbins · Known for Pretty Woman, My Best Friend's Wedding▶ 10:49IMDb ↗Lb ↗

Miles Teller

11 mentions · Bill Simmons, Juliet Litman, Amanda Dobbins · Known for Whiplash▶ 1:21:16IMDb ↗Lb ↗

Rita Wilson

8 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman · Known for Jingle All the Way, Sleepless in Seattle, Runaway Bride▶ 14:19IMDb ↗Lb ↗

Jennifer Lopez

7 mentions · Amanda Dobbins, Juliet Litman · Known for Out of Sight▶ 1:17:31IMDb ↗Lb ↗

Sandra Bullock

6 mentions · Bill Simmons, Juliet Litman · Known for The Proposal, Miss Congeniality, Speed▶ 51:51IMDb ↗Lb ↗

Writers Referenced (3)

Nora Ephron

31 mentions · Bill Simmons, Juliet Litman, Amanda Dobbins · Known for Julie & Julia, When Harry Met Sally...▶ 10:54IMDb ↗Lb ↗

Jeff Arch

20 mentions · Bill Simmons, Juliet Litman, Amanda Dobbins · Known for Sleepless in Seattle▶ 23:34IMDb ↗Lb ↗

Nick Castle

8 mentions · Bill Simmons, Amanda Dobbins · Known for The Last Starfighter▶ 15:42IMDb ↗Lb ↗

Cinematographers Referenced (1)

Gordon Willis

1 mentions · Bill Simmons · Known for The Godfather Part II▶ 49:40IMDb ↗Lb ↗