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‘Cruel Intentions’ With Bill Simmons, Juliet Litman, and Amanda Dobbins

August 22, 2023 · Cruel Intentions (1999) · Drama · Romance · 1:21:46 · ▶ Listen on Spotify

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Most Rewatchable Scene

Amanda Dobbins▶ 32:07Visually memorable montage from the headmaster revealing the cocaine cross to Reese driving the car in slow motion
Bill Simmons▶ 31:59The ending (last five minutes) of the movie, which he calls transcendent
Juliet Litman▶ 32:44The pool scene when he's playing loud music and the cardigans moment

Probably Unanswerable Questions

Amanda Dobbins▶ 42:12The Penn Station timing is a nitpick that doesn't make sense—he couldn't cross the Queensboro Bridge and suddenly be waiting at Penn Station in time
Bill Simmons▶ 41:49Didn't know where the house was located; guessed it could be Rye or Harrison, Westchester
Juliet Litman▶ 41:54House location doesn't make sense for the area; more likely Chappaqua or Katonah given lot sizes, and the Penn Station escalator timing/logistics with her getting off the train don't add up

What's Aged the Best

Amanda Dobbins▶ 44:37The soundtrack - notes it's rare for a 90s soundtrack, especially one aimed at young women, to hold up this well
Bill Simmons▶ 44:31The soundtrack (or Sebastian's car) - picks the soundtrack as what's aged best, also praising the car as a runner-up
Juliet Litman▶ 45:07The soundtrack, though also highlights the real estate/homes in the film as aging amazingly well

What's Aged the Worst

Amanda Dobbins▶ 49:24The homophobia in the film, combined with the internet shaming angle
Bill Simmons▶ 49:22The internet shaming of Terror Raid (the online bullying subplot)

Casting What-Ifs

Amanda Dobbins▶ 49:44Agrees Katie Holmes lacks charisma/energy, jokes that her and Ryan Phillippe would be 'two wet rags' together.
Bill Simmons▶ 49:32Katie Holmes was considered for Annette's role; Bill says she 'would have been good... not as good, but that works.' Director Roger Kumble felt she lacked strength of character for the role.
Juliet Litman▶ 49:55Tries to recall Katie Holmes' filmography (Dawson's Creek, Teaching Mrs. Tingle, brief Batman casting that fell through) but doesn't give a definitive take on the casting what-if itself.

Half-Assed Internet Research

Bill Simmons▶ 54:49Bittersweet Symphony (using the Rolling Stones sample instead of a Smashing Pumpkins song) is the decision that's aged best in Cruel Intentions; also agrees Cruel Intentions is Ryan Phillippe's Apex Mountain
Juliet Litman▶ 55:43Agrees Bittersweet Symphony was a great decision, and that Cruel Intentions is Ryan Phillippe's Apex Mountain

Apex Mountain

Bill Simmons▶ 56:33Agrees Crash is Ryan Phillippe's Apex Mountain; also says Sarah Michelle Gellar's Apex Mountain is this era (1999, Buffy/SNL hosting), and says Reese Witherspoon's Apex Mountain is NOT this movie
Juliet Litman▶ 55:42Ryan Phillippe - this movie (Crash) is his Apex Mountain

Picking Nits

Amanda Dobbins▶ 1:03:01Nitpicks that it's implausible Ness's dad (the dean/headmaster) allows her to write a virginity essay with no oversight; notes the 17 magazine essay plot point feels dated/1999 (compares to Hayley Baldwin/Justin Bieber Vogue piece as modern equivalent); criticizes the car accident scene as 'so slow' and the stunt (shoving her then jumping) as implausible, done just to move the plot forward.
Bill Simmons▶ 1:02:30Where are the parents in this movie? Also nitpicks: trundle bed logistics/where it's acquired; why does Sean Patrick Scott walk out in his underwear with no clothes after being found in the trundle bed; the car accident death scene is 'dumb' and a 'real flaw'—looks like a half-assed suicide/bad jump, and fighting next to a 'highway' (Central Park) is ludicrous; also questions why Reese and Catherine pretend not to know each other in the bathroom at the end despite dating the same guy.
Juliet Litman▶ 1:02:33Questions where the parents are/if they were cast at all; loves the high-end trundle bed and the reveal when the drawer opens; argues the car accident is survivable ('that's the kind of car accident you see a lot in movies and the person tends to survive it') and that the fight scene is poorly staged/looks dumb; explains the bathroom non-acknowledgment as 'a girl thing'/power play.

Best Quote

Amanda Dobbins▶ 1:08:57"I'm the Marsha fucking Brady of the Upper East Side, and sometimes I want to kill myself."
Bill Simmons▶ 1:08:43"This is what I like to call quiet time. It's the time when we reflect on the things we've just done." — calls 'quiet time' the quote of the movie

Who Won the Movie

Amanda Dobbins▶ 1:19:08Sarah Michelle Gellar - she had more to work with and made the script work for her rather than the other way around
Bill Simmons▶ 1:16:57Agrees Sarah Michelle Gellar won the movie
Juliet Litman▶ 1:16:54Sarah Michelle Gellar

Movies Referenced (32)

Scream (1996)

8 mentions · Bill Simmons, Amanda Dobbins▶ 9:15IMDb ↗Lb ↗

Crash (2004)

6 mentions · Bill Simmons, Juliet Litman▶ 21:48IMDb ↗Lb ↗

Dangerous Liaisons (1988)

6 mentions · Bill Simmons, Juliet Litman▶ 7:37IMDb ↗Lb ↗

Pleasantville (1998)

3 mentions · Bill Simmons▶ 14:13IMDb ↗Lb ↗

She's All That (1999)

3 mentions · Juliet Litman, Bill Simmons▶ 6:38IMDb ↗Lb ↗

Superbad (2007)

3 mentions · Bill Simmons▶ 13:39IMDb ↗Lb ↗

American Pie (1999)

2 mentions · Bill Simmons, Juliet Litman▶ 5:07IMDb ↗Lb ↗

Big Daddy (1999)

2 mentions · Bill Simmons▶ 1:20:36IMDb ↗Lb ↗

I Know What You Did Last Summer (1997)

2 mentions · Bill Simmons, Amanda Dobbins▶ 9:10IMDb ↗Lb ↗

Just Go with It (2011)

2 mentions · Bill Simmons, Juliet Litman▶ 1:20:49IMDb ↗Lb ↗

Mean Girls (2004)

2 mentions · Amanda Dobbins, Bill Simmons▶ 44:49IMDb ↗Lb ↗

Sweet Home Alabama (2002)

2 mentions · Bill Simmons▶ 18:31IMDb ↗Lb ↗

Directors Referenced (4)

Roger Kumble

4 mentions · Bill Simmons · Known for Cruel Intentions, The Sweetest Thing, Just Friends▶ 17:32IMDb ↗Lb ↗

Leslie Libman

3 mentions · Bill Simmons▶ 1:35IMDb ↗Lb ↗

Chris Corner

1 mentions · Bill Simmons · Known for The Saint, Open Your Eyes▶ 23:12IMDb ↗Lb ↗

George Clooney

1 mentions · Juliet Litman · Known for The Ides of March, Good Night, and Good Luck., Michael Clayton▶ 59:15IMDb ↗Lb ↗

Actors Referenced (58)

Ryan Phillippe

17 mentions · Bill Simmons, Juliet Litman, Amanda Dobbins · Known for Gosford Park, Crash, Cruel Intentions▶ 4:49IMDb ↗Lb ↗

Sarah Michelle Gellar

17 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman · Known for Cruel Intentions▶ 4:47IMDb ↗Lb ↗

Selma Blair

16 mentions · Bill Simmons, Juliet Litman, Amanda Dobbins · Known for Cruel Intentions, Hellboy, Hellboy II: The Golden Army▶ 11:49IMDb ↗Lb ↗

Reese Witherspoon

12 mentions · Bill Simmons, Juliet Litman, Amanda Dobbins · Known for Wild, Walk the Line, Legally Blonde▶ 4:50IMDb ↗Lb ↗

Christine Baranski

11 mentions · Bill Simmons, Juliet Litman · Known for Mamma Mia!, Chicago, Into the Woods▶ 15:18IMDb ↗Lb ↗

LeBron James

9 mentions · Bill Simmons, Juliet Litman · Known for Trainwreck, Hustle▶ 18:55IMDb ↗Lb ↗

Freddie Prinze Jr.

6 mentions · Juliet Litman, Bill Simmons · Known for She's All That, I Know What You Did Last Summer▶ 55:57IMDb ↗Lb ↗

Power Station

6 mentions · Amanda Dobbins, Juliet Litman · Known for Commando, National Lampoon's European Vacation▶ 30:28IMDb ↗Lb ↗

Richard Side

5 mentions · Amanda Dobbins, Juliet Litman, Bill Simmons · Known for Elf▶ 12:39IMDb ↗Lb ↗

Steve Sanders

5 mentions · Bill Simmons, Juliet Litman▶ 44:02IMDb ↗Lb ↗

Jennifer Lawrence

4 mentions · Bill Simmons, Amanda Dobbins, Juliet Litman · Known for The Hunger Games, Silver Linings Playbook, American Hustle▶ 39:02IMDb ↗Lb ↗

Kate Hudson

4 mentions · Amanda Dobbins, Bill Simmons · Known for Almost Famous, How to Lose a Guy in 10 Days, Bride Wars▶ 38:37IMDb ↗Lb ↗

Writers Referenced (1)

Roger Ebert

6 mentions · Bill Simmons, Amanda Dobbins▶ 17:32IMDb ↗Lb ↗

Cinematographers Referenced (1)

Stamos Triantafyllos

1 mentions · Bill Simmons · Known for Morbius, Wonder Woman, Solo: A Star Wars Story▶ 1:20:00IMDb ↗Lb ↗