The Rewatchables

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

February 24, 2026

Key Takeaways Copied to clipboard!

  • The 2011 film 'Crazy, Stupid, Love' is highly praised on *The Rewatchables* for its perfectly executed ensemble plot structure, which is rare for films of that type. 
  • Steve Carell's performance is defined by his ability to play emotionally decentered but inherently good characters, a quality that makes him uniquely compelling and prevents him from being successfully cast as a villain. 
  • Ryan Gosling and Emma Stone possess electric on-screen chemistry in 'Crazy, Stupid, Love,' which the hosts argue surpasses their chemistry in *La La Land*, cementing them as the defining romantic pairing of their generation. 
  • The chaotic, multi-layered convergence scene featuring Kevin Bacon is considered the 'cherry on top' of *Crazy, Stupid, Love* because it leans into the film's inherent ridiculousness. 
  • Ryan Gosling's metrosexual style, including tight suits and cocktail drinking, is cited as a defining, yet poorly aged, 'most 2011 thing' about the movie, contrasting with Steve Carell's currently fashionable 'dad' aesthetic. 
  • The film's title, *Crazy, Stupid, Love*, is argued to surprisingly track the narrative arc of the movie, moving from 'crazy' and 'stupid' elements to the eventual 'love' resolution. 
  • Steve Carell's performance in ‘Crazy, Stupid, Love’ is considered an underrated showcase of his comedic, vulnerable, and dramatic range, potentially worthy of an Oscar. 
  • The participants debated the plausibility and implications of the babysitter giving explicit photos to the 13-year-old Jacob, contrasting it with older movie tropes. 
  • Ryan Gosling's character in ‘Crazy, Stupid, Love’ was highly influential on the younger male listeners' style, physique, and drinking habits at the time of the movie's release. 

Segments

Movie’s Airplane Appeal
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(00:03:17)
  • Key Takeaway: ‘Crazy, Stupid, Love’ is considered a top-tier airplane movie due to its structure allowing for intermittent viewing.
  • Summary: The film is ranked in the top three airplane movies for its ability to be watched in segments without losing narrative coherence. This makes it ideal for travel where attention may be divided. Other top contenders mentioned include Mean Girls and Edge of Tomorrow.
Strengths of Ensemble Plotting
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(00:04:01)
  • Key Takeaway: The movie excels at weaving together multiple subplots that converge perfectly in the climax, a difficult feat rarely achieved in 2010s ensemble films.
  • Summary: The film successfully manages several concurrent storylines, culminating in a satisfying final scene where all threads connect. This contrasts favorably with similar holiday-themed ensemble movies of the decade that often failed to stick the landing. A subtle clue regarding Emma Stone’s character name, ‘Nana,’ is planted early on.
Steve Carell’s Unique Appeal
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(00:08:06)
  • Key Takeaway: Steve Carell’s comedic strength lies in portraying emotionally decentered but fundamentally good characters, which audiences always root for.
  • Summary: Carell’s success stems from his innate goodness, which prevents audiences from disliking him even when playing flawed characters, unlike some other comedians. This movie showcases his ability to be both secretly handsome and believably off-kilter following his divorce revelation. His film career trajectory shows a dip in major lead comedies before this successful return to his core strengths.
Ryan Gosling’s 2011 Peak
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(00:13:20)
  • Key Takeaway: The year 2011, featuring both Drive and Crazy, Stupid, Love, cemented Ryan Gosling as the ‘coolest white boy in the world’ capable of commanding films silently or with sharp one-liners.
  • Summary: Gosling demonstrated incredible range by starring in the minimalist Drive and this witty romantic comedy in the same year. He was considered the most sought-after actor for independent films around this time, capable of greenlighting projects. His chemistry with Emma Stone in this film is deemed superior to their pairing in La La Land.
Emma Stone’s Generational Talent
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(00:18:45)
  • Key Takeaway: Emma Stone is a ‘24-karat gold performer’ whose early career volume and willingness to embrace vulnerability and silliness position her as a generational talent comparable to Meryl Streep’s early trajectory.
  • Summary: Stone’s early filmography, including Superbad and Easy A, demonstrated a rare combination of being cute, funny, and likable while also being willing to look silly on screen. Her Oscar nomination count at a young age suggests a career trajectory that could rival acting legends. Her chemistry with Gosling in this movie is electric, particularly in their central romantic sequence.
The Gosling/Stone Courting Scene
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(00:44:42)
  • Key Takeaway: The sequence where Hannah returns to Jacob’s place is the film’s best scene, building a believable, sexy, and funny love story in just 10-12 minutes.
  • Summary: This scene, encompassing the rain sequence, the bar pickup, and the bedroom conversation, achieves more emotional depth than entire films. The transition from the ridiculous ‘Dirty Dancing’ conceit to genuine connection is executed flawlessly. The scene’s success lies in the characters surprising each other as their defenses drop.
Masculinity Tropes in Film
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(01:31:15)
  • Key Takeaway: Ryan Gosling’s character, a pickup artist who softens, represents a type of masculinity exploration in film that is rarely depicted harmlessly today.
  • Summary: The movie investigates Gosling’s character’s misogynistic tendencies, which are rooted in his mother’s coldness, providing a complete explanation for his behavior. Modern cinema tends to portray toxic masculinity as an extreme evil rather than a character flaw that can be overcome. The film successfully navigates this by showing his eventual softening.
Rewatchable Scenes and Movie Efficiency
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(00:50:01)
  • Key Takeaway: The ‘crazy everything comes together scene’ featuring Kevin Bacon is the film’s best part, perfectly leaning into its own ridiculousness.
  • Summary: The convergence scene, including the unexpected appearance of Kevin Bacon, is highlighted as the film’s peak moment. This scene is compared to the large-scale misunderstandings common in 1970s sitcoms like Three’s Company. The overall efficiency of Crazy, Stupid, Love is praised because the movie does not waste any scenes or characters.
Critique of Movie’s Climax
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(00:50:39)
  • Key Takeaway: The final 12 minutes of Crazy, Stupid, Love, particularly the climactic speech, are considered too saccharine and slightly detract from the film’s quality.
  • Summary: One participant expressed dislike for the final 12 minutes, feeling that romantic comedies of this type often become overly sentimental at the end. The discussion then pivoted to comparing this ending to successful high school speech climaxes in other films. The ending of Booksmart was mentioned as a graduation scene that successfully pulled off a similar emotional beat.
Most 2011 Elements Identified
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(00:52:05)
  • Key Takeaway: Ryan Gosling’s ‘metrosexual vibe’—including tight suits and cocktail culture—is the most defining, yet poorly aged, 2011 element, contrasting with Carell’s currently fashionable attire.
  • Summary: The cast composition, featuring stars like Emma Stone, Ryan Gosling, and Kevin Bacon together, is noted as being very specific to 2011. Gosling’s fashion sense from that era, described as very GQ but uncool now, is contrasted with Steve Carell’s character’s baggy jeans and polos, which are considered stylish today. The practice of dads driving their young babysitters home is also identified as a dated 2011 social norm, replaced by paying for Ubers.
What Aged Best and Worst
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(00:55:15)
  • Key Takeaway: The Westfield Century City mall is cited as one of the best-aged elements of the film, representing a beautiful, modern, and thriving example of a mall.
  • Summary: The decision to choose between couples getting divorced or staying together was proposed as a potential game show concept. The Westfield Century City mall is lauded as a top-tier LA attraction, especially after its remodel, standing in contrast to the idea that malls are dead. The use of nude photos as a plot device involving the babysitter is identified as something that aged the worst, likely not flying today due to internet culture.
Best Use of Food, Drink, and Character Names
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(01:00:03)
  • Key Takeaway: The vodka cranberries consumed with straws by the characters are the best use of food/drink, leading to a lasting aversion to drinking cocktails with straws.
  • Summary: The vodka cranberries are awarded the Hoonerberg Award for best use of food and drink, making the LA bars in the movie look elegant and desirable. The scene where Ryan Gosling points out how drinking a vodka cranberry with a straw looks led to a real-life aversion to straws for some listeners. David Lindhagen is named the winner of the Chess Rockwell Brock Landers Award for best character name.
Van Lathan Award and Casting Hypotheticals
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(01:02:40)
  • Key Takeaway: The character David Lindhagen should have been played by a Black actor born in 1958, with Giancarlo Esposito being a strong, albeit potentially too sinister, candidate.
  • Summary: The Van Lathan Award was given because one character, David Lindhagen, could have been recast with a Black actor. The hosts explored actors born in Kevin Bacon’s birth year (1958), considering Ice T and Keenan Ivory Wayans, before settling on Giancarlo Esposito. The consensus was that Kevin Bacon’s character works because he is believably just handsome enough to be an accountant who women would sleep with, which ruled out overly handsome choices like Blair Underwood.
Title Critique and Narrative Arc
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(01:05:28)
  • Key Takeaway: While widely considered one of the worst titles of the last 20 years, Crazy, Stupid, Love arguably works because it mirrors the film’s narrative progression.
  • Summary: Steve Carell reportedly hated the title, and the hosts agreed that a group of college guys would never ask to see tickets for Crazy, Stupid, Love. The poster, featuring Marisa Tomei through legs, is deemed misleading as it suggests a sex comedy rather than the film’s actual content. One host argued the title tracks the story: starting crazy, becoming stupid, and ending with love.
Weakest Links and Unbelievable Plot Points
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(01:07:45)
  • Key Takeaway: The biggest nitpick is the implausibility of Ryan Gosling’s character frequenting the same LA bar nightly, mixing ages, and the babysitter being in love with Steve Carell’s character.
  • Summary: The babysitter plot point involving nude photos sent to a 14-year-old is considered the worst-aged element, likely due to modern internet scrutiny. The constant presence of all main characters at the same bar is deemed unrealistic for Los Angeles, where bar demographics shift significantly by time of night. The babysitter’s attraction to Carell’s character is also seen as a significant stretch of believability.
The Marriage Halftime Theory
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(01:25:22)
  • Key Takeaway: The plot of Crazy, Stupid, Love functions as a story about a marriage halftime, where Julianne Moore’s character initiates a break, prompting Steve Carell’s character to sleep with nine women.
  • Summary: The film is framed as a narrative where the marriage takes a break, initiated by the wife’s affair, which then allows the husband to explore his own sexual freedom. This structure is deemed necessary for the audience to still root for Carell’s character, as the wife’s initial infidelity serves as the ‘original sin.’ The hosts conclude that real-life marriage halftimes rarely work when one party cheats prolifically first.
Babysitter Crush and Hypocrisy
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(01:37:51)
  • Key Takeaway: The possibility of the babysitter having a crush on Steve Carell’s character was dismissed, and the hypocrisy of Cal’s wife being mad about him sleeping with the teacher was noted.
  • Summary: The panel concluded the babysitter likely did not have a crush on Cal. They pointed out the hypocrisy of Cal’s wife being upset about his affair with the teacher. A potential continuity error regarding a bad stunt double in the Dirty Dancing scene was also mentioned.
Prestige TV Sequel Potential
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(01:38:07)
  • Key Takeaway: The film could potentially work as a Prestige TV series, similar to how The Burbs was adapted, allowing for deeper character exploration.
  • Summary: The idea of a sequel, prequel, or prestige TV version of ‘Crazy, Stupid, Love’ was entertained, drawing parallels to successful movie-to-series adaptations like The Burbs. The structure would require bringing all character arcs together in a final scene while expanding time with each individual. The format might suit an Apple TV+ or Bill Lawrence-style show.
Imitation Category Skip
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(01:39:07)
  • Key Takeaway: The ‘Is This Movie Better With…’ imitation category was skipped because the previous week’s Zane Lowe impression was considered a high bar, and no one prepared an imitation.
  • Summary: The segment dedicated to imitating characters like Wayne Jenkins or Fergie the Florist was skipped for this episode. This decision followed a highly successful Zane Lowe impression from the prior week, which set a difficult standard. The cast noted that the movie’s strong casting made replacing any actor difficult.
Steve Carell Oscar Worthy Performance
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(01:39:56)
  • Key Takeaway: Steve Carell’s performance in the film is considered highly underrated, demonstrating his full range from comedy to vulnerability, and he was nominated for a Golden Globe.
  • Summary: The panel agreed that Steve Carell delivered a really good performance, showing nearly everything he can do, including dramatic depth when conversing with Ryan Gosling. Carell was nominated for a Golden Globe for this role, though Christopher Plummer won the Oscar that year for Beginners.
Ryan Gosling Oscar Snub Debate
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(01:41:04)
  • Key Takeaway: Ryan Gosling’s performance in ‘Crazy, Stupid, Love’ is argued to be superior to Jonah Hill’s nominated performance in Moneyball that year.
  • Summary: The discussion centered on the Best Supporting Actor category, suggesting Gosling could have replaced Jonah Hill in Moneyball. Listeners believe Gosling’s work here is comparable to his performance in Barbie, and he is generally considered to win most movies he stars in.
Babysitter Arrest and Age Confusion
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(01:41:47)
  • Key Takeaway: The ages of the babysitter (17) and the boy (13) were confusing, but the act of giving naked pictures to a 13-year-old was deemed corny and unrealistic, though not the main flaw.
  • Summary: The panel questioned if the babysitter faced arrest for giving photos to the 13-year-old, noting the age difference (17 and 13). The characters’ stated ages (e.g., Julianne Moore being 44) seemed compressed to justify Steve Carell and his wife having a child who was graduating eighth grade. The consensus was that while the photo exchange was weird, the age dynamic itself was less bothersome than the premise.
Jacob’s Job and Trust Fund Life
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(01:44:06)
  • Key Takeaway: Jacob, Ryan Gosling’s character, appears to have inherited wealth and spends his time working out, leading to speculation about his lack of conventional employment.
  • Summary: Jacob is established as having inherited wealth, leading to the unanswerable question of what he did all day besides working out and going to bars. The panel joked that in 2011, guys like him didn’t have podcasts to broadcast their lifestyle, unlike today. His dedication to fitness, evidenced by handstand push-ups, suggests significant time commitment to his physique.
Unwanted Memorability and Harsh Criticism
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(01:45:55)
  • Key Takeaway: The most unwanted piece of memorability from the film is the explicit photos, while the harshest criticism Cal received was his wife blaming him for losing sight of what kept her content.
  • Summary: Bill Simmons explicitly stated he did not want the photos as his piece of memorability from the movie. The most brutal line delivered in the film was Cal’s wife telling him she cheated because he lost sight of what it took to keep her content as a man and husband.
Double Feature Chemistry Comparison
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(01:46:43)
  • Key Takeaway: Mina Kimes argues that Ryan Gosling and Emma Stone have better on-screen chemistry in ‘Crazy, Stupid, Love’ than they do in La La Land.
  • Summary: Mina Kimes proposed a double feature of this film followed by La La Land to prove the superior chemistry between Gosling and Stone in the 2011 movie. The panel also suggested pairing it with Focus due to the similar themes of relationship manipulation, though Hitch was proposed as a better Will Smith comparison.
Rom-Com Influence and Style Imitation
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(01:50:00)
  • Key Takeaway: For one panelist, ‘Crazy, Stupid, Love’ is the defining romantic comedy of their generation, heavily influencing their style, physique goals, and cocktail choices at age 17.
  • Summary: The film was called the best rom-com of the 2000s (though released in 2011) and was highly influential on a panelist who turned 17 that weekend. This influence included searching for Gosling’s exact sunglasses, adopting V-necks, and starting to drink Old Fashioneds. The panel also praised the effective emotional scene where Carell waters the lawn while looking through the window at Julianne Moore.
Cameos and Supporting Roles Noted
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(01:51:46)
  • Key Takeaway: The film features several notable supporting actors, including Josh Groban and Carolina Wiedra, who was later seen in the series Pluribus.
  • Summary: The conversation briefly acknowledged unmentioned bit characters, specifically Josh Groban, who is described as weird but funny in the movie. It was noted that Carolina Wiedra, who plays one of the women Cal hits on, also appears in the series Pluribus.
Upcoming CR Month Schedule
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(01:55:13)
  • Key Takeaway: The next five episodes constitute ‘CR Month,’ kicking off with a live rewatch of Sicario on March 2nd at 6 PM ET.
  • Summary: The upcoming run of five episodes will be entirely comprised of Chris’s (CR’s) movie choices, starting with Sicario. This live rewatch event is scheduled for March 2nd at 6 PM ET (3 PM PT), fulfilling a long-standing request from CR.