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‘Crazy, Stupid, Love’ With Bill Simmons, Van Lathan, and Mina Kimes

February 24, 2026 · Crazy, Stupid, Love. (2011) · Comedy · Drama · Romance · 1:55:33 · ▶ Listen on Spotify

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Stephen A. Smith Hottest Take Award

Bill Simmons▶ 24:19Early 2000s Emma Stone (EZA, Crazy Stupid Love, Superbad era) was like seeing a great lottery pick - comparable to seeing Mahomes early or LeBron in '05, where you could tell we were going to go on a ride
Bill Simmons▶ 24:19Early-era Emma Stone (Superbad/Easy A/Crazy Stupid Love) was one of the great 'lottery picks' -- you could tell she'd be a superstar the way you could see early Mahomes or 2005 LeBron; La La Land was the coronation but this era was the setup.
Mina Kimes▶ 17:57Ryan Gosling and Emma Stone's chemistry in Crazy Stupid Love is so much better than La La Land, and the romantic scene in this movie is better than any scene in La La Land
Mina Kimes▶ 25:39Supported the take rather than giving her own: Superbad is the incredible showcase -- a would-be thankless role where she's so funny and cool you can tell she's a star; 'she is so cute, so funny, so likable... the dream girl.'
Van Lathan▶ 26:32Built on Bill's take rather than giving his own (his comes later per Bill's setup): compared her rise to early Mike Tyson's volume -- eight movies from 2007-2010 building audience familiarity before Easy A made her a lead.

Horlbeck Runtime Scale

Bill Simmons▶ 34:48Plus 8 minutes (could cut out 10 minutes from the plus 18)

Most Rewatchable Scene

Bill Simmons▶ 36:12Multiple scenes including the opening scene where Emily asks for a divorce and Cal jumps out of the car, Jacob meets Hannah and her friend at the bar, the shopping montage, and several other scenes throughout the movie
Mina Kimes▶ 40:10Agrees the shopping montage is one of the three best scenes in the movie because it's funny and the makeover transformation is so effective
Van Lathan▶ 36:49Discusses the Jacob meets Hannah scene, emphasizing how it establishes Jacob's character when she rejects him 50 times but doesn't pierce his confidence, and praises the shopping montage as effective

Hall of Fame Plaque

Bill Simmons▶ 44:36Hannah goes back to Jacob's place - the courting scene with dirty dancing transitioning to the bedroom
Mina Kimes▶ 45:50The entire sequence of her going back in the rain to the bar, picking him up, going back to the house, transitioning from dirty dancing to the bedroom
Van Lathan▶ 45:03Hannah goes back to Jacob's place - the scene where they keep surprising each other and get to know each other with defenses down

What's Aged the Best

Bill Simmons▶ 58:40Kevin Bacon as a romantic antagonist - praising his ability to play the smarmy scumbag role
Mina Kimes▶ 59:05The jokes in the movie generally have aged really well, including side comments and physical comedy moments
Van Lathan▶ 55:50The Westfield Century City Mall - calls it 'maybe one of the things that's aged the best of anything in my entire Rewatchables career' and 'the term cuckold'

Great Shot Gordo Award

Bill Simmons▶ 59:44When Steve Carell and Julianne Moore are sitting in chairs far apart with a chair between them

Big Kahuna Burger Award

Bill Simmons▶ 59:56vodka cranberries
Mina Kimes▶ 1:00:17discussed the vodka cran scene with Ryan Gosling drinking with a straw and how the movie taught life lessons about men not using straws or drinking girl cocktails
Van Lathan▶ 1:00:00discussed how the movie makes you want to go to LA bars because they look elegant, clean, and cool

Is There a Better Title?

Bill Simmons▶ 1:07:03The Makeover
Mina Kimes▶ 1:07:25How to Pick Up Women
Van Lathan▶ 1:06:26Defends the original title, explaining it tracks the narrative arc of the movie (crazy, then stupid, then love)

Butch's Girlfriend Award

Bill Simmons▶ 1:08:04The bar scenes - specifically that Hannah would never run into her dad at the same bar, and that Ryan Gosling goes to the same bar every night
Mina Kimes▶ 1:08:45The unrealistic bar dynamic where 20-somethings and 40-somethings both go to the same bar to pick people up
Van Lathan▶ 1:08:34The same bar issue - that Ryan Gosling goes to the same bar four nights a week and everyone uses the same bar

What's Aged the Worst

Bill Simmons▶ 1:11:26All the babysitter stuff - it just wouldn't fly now, especially giving the photos to the eighth grader at the end
Mina Kimes▶ 1:13:35Pickup culture at bars generally is just not what it was in 2011
Van Lathan▶ 1:12:55Young people being interested in having sex with other people and willing to talk to them to make it happen - the whole pickup culture at bars

Dion Waiters Award

Bill Simmons▶ 1:23:57Marisa Tomei — Marissa Tomei

Apex Mountain

Bill Simmons▶ 1:32:03Ryan Gosling — Ryan Gosling - La La Land; Emma Stone - La La Land; Julianne Moore - late 90s post Boogie Nights; Steve Carell - mid 2000s with The Office, Little Miss Sunshine, 40 Year Old Virgin and Anchorman; Singles bars in 21st century movies - yes; Dirty dancing homages - yes; Century City Mall - right now (2026)
Mina Kimes▶ 1:31:47Ryan Gosling — Mentioned Ken and Barbie for Gosling where he was nominated and sings, called it tough to decide; discussed their on-screen chemistry; agreed Century City Mall keeps getting better
Van Lathan▶ 1:32:11Ryan Gosling — Ryan Gosling - La La Land, but acknowledges the combination of this movie and Drive is pretty good; Steve Carell - mid 2000s period when he got Oscar nomination for Little Miss Sunshine

Hanks or Cruise

Bill Simmons▶ 1:35:35Tom Cruise — Initially said Hanks clearly, but after discussion settled on Cruise as Gosling and Hanks as Carell
Mina Kimes▶ 1:35:10Tom Cruise — Young Cruise (like cocktail Cruise) as Gosling would have been great
Van Lathan▶ 1:35:25Tom Cruise — Cruise as Gosling - he could have definitely pulled that off

Probably Unanswerable Questions

Bill Simmons▶ 1:41:56Was the babysitter eventually arrested? What was Jacob's job?
Mina Kimes▶ 1:42:06Ages in the movie are confusing - they compressed all ages to make the plot work, with characters' stated ages not matching actors' apparent ages
Van Lathan▶ 1:43:05Agreed that ages were problematic and compared it to inappropriate age dynamics in 80s movies that we now know were wrong

Coach Finstock Life Lesson

Bill Simmons▶ 1:46:18Straws are phallic
Van Lathan▶ 1:46:24The scene where Cal is told the meanest thing - that his wife cheated on him because he lost sight of what it took to keep her content as a man, husband, and lover

Best Double Feature

Bill Simmons▶ 1:47:49Focus — Focus because the movies complement each other with the same director
Mina Kimes▶ 1:46:55La La Land — This movie paired with La La Land to compare Gosling and Stone's chemistry
Van Lathan▶ 1:47:21Pretty Woman

Who Won the Movie

Bill Simmons▶ 1:49:33Ryan Gosling — Gosling - 'It's his movie' and 'he wins almost every movie he's in'
Mina Kimes▶ 1:49:32Ryan Gosling — Gosling - agreed with the consensus
Van Lathan▶ 1:49:32Ryan Gosling — Gosling - agreed with the consensus

Movies Referenced (66)

La La Land (2016)

16 mentions · Bill Simmons, Mina Kimes, Van Lathan▶ 17:34IMDb ↗Lb ↗

Focus (2015)

14 mentions · Van Lathan, Bill Simmons▶ 7:09IMDb ↗Lb ↗

Pretty Woman (1990)

8 mentions · Bill Simmons, Mina Kimes, Van Lathan▶ 25:12IMDb ↗Lb ↗

Dirty Dancing (1987)

7 mentions · Bill Simmons, Van Lathan, Mina Kimes▶ 20:11IMDb ↗Lb ↗

Barbie (2023)

5 mentions · Van Lathan, Mina Kimes, Bill Simmons▶ 16:25IMDb ↗Lb ↗

Superbad (2007)

5 mentions · Bill Simmons, Van Lathan▶ 18:45IMDb ↗Lb ↗

Hitch (2005)

4 mentions · Van Lathan, Bill Simmons▶ 1:16:04IMDb ↗Lb ↗

Zombieland (2009)

4 mentions · Mina Kimes, Van Lathan▶ 19:56IMDb ↗Lb ↗

Fight Club (1999)

3 mentions · Van Lathan▶ 1:16:55IMDb ↗Lb ↗

Get Smart (2008)

3 mentions · Bill Simmons▶ 8:17IMDb ↗Lb ↗

Lady Bird (2017)

3 mentions · Bill Simmons▶ 36:18IMDb ↗Lb ↗

Little Miss Sunshine (2006)

3 mentions · Bill Simmons, Van Lathan▶ 8:09IMDb ↗Lb ↗

Directors Referenced (5)

George Clooney

10 mentions · Bill Simmons, Mina Kimes, Van Lathan · Known for The Ides of March, Good Night, and Good Luck., Michael Clayton▶ 12:32IMDb ↗Lb ↗

Tom Brady

7 mentions · Bill Simmons, Mina Kimes, Van Lathan · Known for The Hot Chick▶ 21:38IMDb ↗Lb ↗

Ben Affleck

2 mentions · Mina Kimes, Bill Simmons · Known for Argo, Gone Girl, The Town▶ 1:26:58IMDb ↗Lb ↗

John Hughes

1 mentions · Van Lathan · Known for Planes, Trains & Automobiles, Uncle Buck, The Breakfast Club▶ 1:43:19IMDb ↗Lb ↗

Kim Fields

1 mentions · Van Lathan · Known for What to Expect When You're Expecting▶ 1:20:39IMDb ↗Lb ↗

Actors Referenced (71)

Ryan Gosling

46 mentions · Van Lathan, Bill Simmons, Mina Kimes · Known for Blue Valentine, La La Land, Drive▶ 7:07IMDb ↗Lb ↗

Steve Carell

34 mentions · Van Lathan, Mina Kimes, Bill Simmons · Known for The 40-Year-Old Virgin, Foxcatcher▶ 5:44IMDb ↗Lb ↗

Meryl Streep

12 mentions · Bill Simmons, Van Lathan, Mina Kimes · Known for Mamma Mia!, Out of Africa▶ 19:18IMDb ↗Lb ↗

Anon Mall

9 mentions · Van Lathan, Bill Simmons · Known for The Matrix Resurrections, John Wick: Chapter 4▶ 55:54IMDb ↗Lb ↗

Julianne Moore

9 mentions · Bill Simmons, Van Lathan, Mina Kimes · Known for Far from Heaven, Boogie Nights, Magnolia▶ 7:04IMDb ↗Lb ↗

Tom Cruise

8 mentions · Mina Kimes, Van Lathan, Bill Simmons · Known for Top Gun, Mission: Impossible II, Minority Report▶ 25:28IMDb ↗Lb ↗

Will Smith

8 mentions · Van Lathan, Bill Simmons, Mina Kimes · Known for Men in Black, I Am Legend▶ 49:22IMDb ↗Lb ↗

Billy Dee Williams

7 mentions · Van Lathan, Bill Simmons · Known for Star Wars: Episode V - The Empire Strikes Back, Star Wars: Episode VI - Return of the Jedi, The Lego Batman Movie▶ 1:18:27IMDb ↗Lb ↗

Daryl Hannah

7 mentions · Van Lathan, Bill Simmons · Known for Wall Street, Kill Bill: Vol. 1, Kill Bill: Vol. 2▶ 6:24IMDb ↗Lb ↗

Andrew Westfield

6 mentions · Van Lathan, Bill Simmons▶ 55:53IMDb ↗Lb ↗

Kevin Bacon

6 mentions · Bill Simmons, Van Lathan, Mina Kimes · Known for Footloose, Hollow Man▶ 41:23IMDb ↗Lb ↗

Real Life

6 mentions · Van Lathan, Bill Simmons · Known for Once Bitten▶ 8:17IMDb ↗Lb ↗

Writers Referenced (5)

Dan Fogelman

2 mentions · Bill Simmons, Van Lathan▶ 6:37IMDb ↗Lb ↗

Kurt Warner

1 mentions · Bill Simmons▶ 1:20:08IMDb ↗Lb ↗

Michael Dinner

1 mentions · Bill Simmons▶ 8:17IMDb ↗Lb ↗

Roger Ebert

1 mentions · Bill Simmons▶ 34:57IMDb ↗Lb ↗

Taylor Sheridan

1 mentions · Van Lathan · Known for Hell or High Water, Wind River▶ 33:25IMDb ↗Lb ↗

Cinematographers Referenced (2)

Michael Grantland

1 mentions · Bill Simmons · Known for The Taking of Pelham 123, The Other Guys▶ 1:09:52IMDb ↗Lb ↗

Michael Scott

1 mentions · Mina Kimes · Known for Speed, Twister, Donnie Darko▶ 12:32IMDb ↗Lb ↗