Podcast Summary: The Rewatchables – ‘The Legend of Billie Jean’ With Bill Simmons and Chris Ryan

Podcast: The Rewatchables (The Ringer)
Episode: 'The Legend of Billie Jean'
Date: September 9, 2025
Hosts: Bill Simmons, Chris Ryan, Craig Horlbeck, Sierra McClain

Overview

This episode of The Rewatchables dives into the cult favorite The Legend of Billie Jean (1985), a mid-80s “VHS classic” beloved for its mix of teenage rebellion, pop music, female empowerment, and pure 80s nostalgia. Hosts Bill Simmons and Chris Ryan, joined by Craig Horlbeck and Sierra McClain, dissect the movie’s themes, its place in 80s pop culture, and why it continues to resonate, even if it was never a mainstream blockbuster. The conversation blends personal reminiscence, critical analysis, and trademark Ringer humor.

Main Discussion Points and Insights

The Movie as a "One For Us" Rewatchable

• Nostalgia Factor: All the hosts connect deeply with the era, describing how these mid-80s films replayed constantly during their childhoods and defined their formative pop-cultural experiences.
  • Chris Ryan (03:14): “One of the most nostalgic movie-going experiences I can have right now is to watch this... these movies were just the wallpaper, they were on all the time.”
• Genre Positioning: The film sits among a pantheon of similar underdog/fantasy teen movies—Karate Kid, The Last Starfighter, Big Trouble in Little China—with high rewatch value, teen heroes, and memorable soundtracks.

Female Empowerment and Subtle Radicalism

• Ahead of Its Time: The hosts highlight the film’s boldness in foregrounding a female protagonist exerting agency and confronting misogyny—a rarity in its era.
  • Bill Simmons (05:55): "There’s a female empowerment hero piece... dare I say ahead of its time."
  • Chris Ryan (06:30): "It’s wild, but there’s so much casual misogyny in this movie... The whole thing basically gets rolling because Mr. Pyatt tries to sexually assault her and then flip it on her."
• Viral Celebrity Before Social Media: The movie eerily presages Internet and viral fame, with Billie Jean’s image spreading rapidly until she becomes a folk hero, a parallel the hosts draw with today’s online virality.
  • Chris Ryan (06:30): "The idea of somebody becoming an overnight sensation and taking over—now it can just be instantaneously."
  • Bill Simmons (11:25): "This movie does see this world coming... her becoming a viral celebrity with the ‘fair is fair’ hashtag."

80s Cultural and Cinematic Hallmarks

• Soundtrack as Character: The use of Pat Benatar’s “Invincible” and other 80s artists is dissected, showing how these sound cues not only defined the vibe but were also essential marketing (playing the song three times in a 95-minute movie).
  • Chris Ryan (10:39): "It’s used as a theme in the score itself… The movie being right on the cusp of a change in media."
• Kids vs. Adults Dynamic: The 80s trope of “kids as the good guys” and “adults as the enemy” is strong here, something the hosts note doesn’t exist in quite the same way today.
  • Bill Simmons (18:40): "Kids were the good guys and adults were just bad… this doesn’t really exist now in the same way."
• The 80s Mall Aesthetic: Extended discussion about the nostalgia of 80s mall culture, seen as a lost communal staple that the movie captures perfectly.
  • Sierra McClain (32:57): "I caught the tail end of malls in my childhood... it's the most nostalgic era."

Character and Actor Retrospectives

• Helen Slater and 80s Crushes: The hosts reminisce about iconic 80s actresses who played high schoolers, with Helen Slater rating highly as a beloved archetype.
  • Bill Simmons (22:01): "Helen Slater and Billie Jean… Elizabeth Shue in Karate Kid... those were the five."
• Christian Slater’s Debut: Noting his real-life crush on Helen Slater during filming, and his surprising performance as the plucky younger brother.
• Supporting Weirdos and Villains: Shoutouts to quirky side characters (like Hubie and the mustachioed cops), and the slimy villainy of Mr. Pyatt.

The Movie’s Enduring "Cult" Status and Flaws

• Box Office Bomb, Cable Hit: The film grossed only $3-4 million but became a cable and VHS classic echoed in later youth media.
  • Bill Simmons (27:27): "It made 3.1 million... but was on cable for the next 15 years."
• Cheesy, Earnest, and Sometimes Silly: The hosts admit the film has its flaws—implausible plot points and certain aged poorly elements—but celebrate its sincerity and time-capsule quality.
  • Chris Ryan (35:39): "That character’s all over the place... But at that time, that was what horror was."

Big Themes & Meta-Observations

• Notoriety vs. Fame: Highlighted as a central and prescient concept by the film’s director and called out as the precursor to OJ/Kato Kaelin/Internet celebrity culture.
  • Bill Simmons (16:13): "I was fascinated with notoriety getting confused with fame... starts right here in the mid-80s."
• Does ‘Fair Is Fair’ Mean Anything Now? The meme-ification of Billie Jean’s slogan is compared to today’s viral phrases/catchphrases.

Notable Quotes & Memorable Moments

On 80s Nostalgia and the Setting

• Bill Simmons (03:07):
  "Just take me back to the mid-80s when life was simple and we just had malls and we could just have people get innocently shot in the shoulder and become heroes and then just get away scot-free."

• Chris Ryan (04:05):
  "They’re not American cinematic classics, but they are like my VHS classics."

On Billie Jean as a Feminist Character

• Chris Ryan (06:51):
  "It’s wild, but there’s so much casual misogyny in this movie. The whole thing basically gets rolling because Mr. Pyatt tries to sexually assault her and then flip it on her..."

• Bill Simmons (09:40):
  "She’s such a good character… At the first half hour she’s really innocent and shy... and then by the end, she’s the fucking badass."

On Virality and Media

• Bill Simmons (11:48):
  "Once upon a time... Pump Up the Volume created podcasting. I think this movie created the Internet."

• Chris Ryan (12:26):
  "It points out a couple things... kids are starting to get their hands on video cameras... and they’re starting to tape stuff more."

Most Rewatchable Scenes

• Bill Simmons (29:37):
  "Would you throw the opening credits in here with the Divinyls 'Boys in Town’?"

• Chris Ryan (39:04):
  "Her coming out of the scene at Lloyd’s house and making the tape the first time... that's my favorite line: ‘You look famous.’"

On Culture & Technology

• Bill Simmons (43:36):
  "I honestly could have used more of in the 80s and 90s—when characters found an empty, really nice suburban semi-mansion to hide in for a couple days. Why did we stop doing this?"

Timestamps for Key Segments

• [03:14] – The hosts’ foundational VHS memories and the significance of 80s movie wallpaper
• [05:55] – The film’s female empowerment angle and ahead-of-its-time status
• [10:08] – Music in 80s movies and Pat Benatar’s “Invincible” as a film motif
• [16:13] – Notoriety vs Fame discussion – predicting viral/Internet celebrity
• [22:01] – Breakdown of top 80s teen “crushes” and Helen Slater’s place among them
• [27:27] – The film’s box office failure vs. rewatchable legacy
• [29:37] – Most rewatchable scenes: opening credits, mall chase, hair reveal, and others
• [32:57] – Deep dive on 80s mall culture and its place in the film
• [40:00] – Discussion of the most 1985 things about the movie (scooters, Panama Jack, gas prices, Beta cams)
• [43:36] – “Best aged” aspects of the film – hidden house trope, 80s movie villains, fashion
• [51:14] – Weakest links and low points, and the “save Kenny” subplot
• [53:02] – Overuse (or not) of Pat Benatar’s “Invincible”
• [54:12] – Costume continuity issues (wig in reshoots)
• [66:05] – Apex Mountain for Helen Slater and comparisons to other 80s stars
• [73:52] – Nitpicking the plot: improbable hiding, police response, and logic holes
• [80:17] – Double feature suggestions
• [81:07] – First-time viewer Craig reviews the film

Fun Debates & Flex Categories

• Alternative Soundtrack Choices: Hosts playfully imagine which other classic 80s songs would have energized key sequences.
  • Chris Ryan (61:10): “Voices Carry by ‘Til Tuesday” for the escape scene!
• Sequel/Prestige TV Re-imaginings: Imagining a gritty, Inglesby-esque limited series set in Corpus Christi with darker modern themes.
• Apex Mountain: Which actors, vehicles, or character names peaked in this film?
  • e.g., Is Billie Jean the apex for "Fair is Fair" as a cultural phrase? For short-haired 80s women?
• Casting What-Ifs: Would young James Spader or John Cusack have made a better Lloyd?

Modern Resonance & Final Thoughts

• The film is alternately described as charmingly dated and surprisingly forward-thinking. The group agrees it functions as a fascinating cultural time capsule for 1985.

  • Craig Horlbeck (81:14): "I really enjoyed this movie… kind of always toe the line between genuine love and ironic love for them. But that’s part of the fun of these 80s movies."

• The central group (Billie Jean, Binks, Putter, Ophelia) is a “good hang,” and Corpus Christi as a setting is unexpectedly fresh.

  • Sierra McClain (82:15): “This movie is aggressively representing culture at this exact time... I think a lot of stuff now doesn’t.”

Conclusion

The Legend of Billie Jean may be light in plot and heavy on cheese, but it is celebrated for its authenticity, earnestness, and prescience with themes of rebellion, viral celebrity, and the fight for fairness. The hosts revel in their memories and the 80s time-capsule vibe, finding both humor and unexpected depth in the film—and reminding listeners why the movie is, in the end, so endlessly rewatchable.

Select Notable Quotes with Timestamps

• “She’s such a good character… by the end, she’s the fucking badass.” – Bill Simmons [09:40]
• “The whole thing gets rolling because Mr. Pyatt tries to sexually assault her and then flip it on her.” – Chris Ryan [06:51]
• “This movie does see this world coming... her becoming a viral celebrity with the ‘fair is fair’ hashtag.” – Bill Simmons [11:12]
• “I honestly could have used more of in the 80s and 90s… characters found an empty, really nice suburban semi-mansion to hide in for a couple days.” – Bill Simmons [43:36]
• “This movie is aggressively representing culture at this exact time.” – Sierra McClain [81:57]

For fans of 80s films, pop culture analysis, and spirited group debates, this Rewatchables episode is both a reminder of childhood media magic and a smart reconsideration of underrated classics like Billie Jean. Fair is fair.