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‘The Legend of Billie Jean’ With Bill Simmons and Chris Ryan

September 9, 2025 · The Legend of Billie Jean (1985) · Action · Drama · 1:23:12

IMDb ↗Letterboxd ↗

Categories

Apex Mountain

Bill Simmons▶ 20:21Helen Slater — Discussed Helen Slater's career peak during mid-80s run (Supergirl, Billie Jean, Ruthless People, Secret of My Success, City Slickers) and Christian Slater's first big movie before Heathers breakthrough
Chris Ryan▶ 24:19Christian Slater — Agreed with discussion of Christian Slater's early career moment and provided context about the competitive movie landscape of July 1985

Most Rewatchable Scene

Bill Simmons▶ 28:56Opening credits with The Divinyls 'Boys in Town', Billie Jean harassment scene with Mr. Pyatt, mall exchange with sped-up 'Rebel Yell', Billie Jean watching Joan of Arc and new haircut reveal, Billie Jean's tape being played at police station
Chris Ryan▶ 29:09Agrees with opening credits for authentic location feel, discusses mall scene extensively wanting more 80s mall stores, and Lloyd's rich guy house with bedroom slide to pool
Craig Horlbeck▶ 32:22Focuses on mid-80s mall nostalgia and how it's the most nostalgic era, discusses the cultural significance of mall scenes

Stephen A. Smith Hottest Take Award

Bill Simmons▶ 46:54Stranger Things creators studied this movie (along with E.T., Goonies, and Karate Kid) and would admit it if given truth serum
Chris Ryan▶ 46:50Agrees with the Stranger Things take and adds that there was Karate Kid influence, specifically Eleven's haircut

Big Kahuna Burger Award

Bill Simmons▶ 47:07Milkshake being dumped on a movie bully
Chris Ryan▶ 47:24Shopping cart full of junk food that Potter tries to buy at the convenience store

Probably Unanswerable Questions

Bill Simmons▶ 49:29What happened the next day?
Chris Ryan▶ 49:41Discussion about the character's unrealistic expectations of Vermont based on a poster
Craig Horlbeck▶ 49:55Tangential question about whether kids still hang up posters of women in their rooms

Butch's Girlfriend Award

Bill Simmons▶ 50:23Either Billie Jean saving Kenny the Random Abuse Kid section, or Billie Jean getting shot at by two people trying to get a ransom section
Chris Ryan▶ 50:47The child abuse section where it's just like 'you got to save Kenny' but 'I'm on the run from the law, so I can't do that'

Casting What-Ifs

Bill Simmons▶ 59:17Couldn't find any casting what-ifs
Chris Ryan▶ 59:18Couldn't find any casting what-ifs

Dion Waiters Award

Bill Simmons▶ 1:00:22Yeardley Smith — Putter
Chris Ryan▶ 1:00:00Dean Stockwell

Is This Movie Better With

Bill Simmons▶ 1:17:37Chris Russo — Mad Dog Russo as the DA
Chris Ryan▶ 1:16:59Peter Schrager — Peter Schrager (new addition to the category)

Just One Oscar

Bill Simmons▶ 1:18:02Pat Benatar — Pat Benatar for Best Original Song with 'Invincible'
Chris Ryan▶ 1:18:08Jeffrey Kimball — Jeffrey Kimball for Best Cinematography

Best Double Feature

Bill Simmons▶ 1:20:37The Terminator — The Terminator - for female empowerment heroes from the mid-'80s pairing Sarah Connor and Billie Jean
Chris Ryan▶ 1:20:46The Last Starfighter — Last Starfighter or Rad - classic cult VHS movies from this time period

Who Won the Movie

Chris Ryan▶ 1:20:54Helen Slater — Possibly suggesting Helen Slater won the movie

Coach Finstock Life Lesson

Bill Simmons▶ 1:20:56Fair is fair

Movies Referenced (44)

Top Gun (1986)

7 mentions · Bill Simmons, Chris Ryan▶ 9:46IMDb ↗Lb ↗

City Slickers (1991)

4 mentions · Chris Ryan, Bill Simmons▶ 23:09IMDb ↗Lb ↗

The Messenger: The Story of Joan of Arc (1999)

4 mentions · Bill Simmons, Chris Ryan▶ 33:22IMDb ↗Lb ↗

Just One of the Guys (1985)

3 mentions · Bill Simmons▶ 5:42IMDb ↗Lb ↗

Pump Up the Volume (1990)

3 mentions · Bill Simmons▶ 11:04IMDb ↗Lb ↗

Vision Quest (1985)

3 mentions · Bill Simmons, Chris Ryan▶ 9:48IMDb ↗Lb ↗

Back to the Future (1985)

2 mentions · Chris Ryan, Bill Simmons▶ 24:20IMDb ↗Lb ↗

Beverly Hills Cop (1984)

2 mentions · Chris Ryan, Bill Simmons▶ 24:46IMDb ↗Lb ↗

Jaws 2 (1978)

2 mentions · Bill Simmons, Craig Horlbeck▶ 58:30IMDb ↗Lb ↗

Teen Wolf (1985)

2 mentions · Bill Simmons▶ 46:08IMDb ↗Lb ↗

A Midnight Clear (1992)

1 mentions · Chris Ryan▶ 58:37IMDb ↗Lb ↗

Alien (1979)

1 mentions · Chris Ryan▶ 1:10:07IMDb ↗Lb ↗

Directors Referenced (4)

Keith Gordon

7 mentions · Bill Simmons, Chris Ryan · Known for A Midnight Clear▶ 13:02IMDb ↗Lb ↗

Ken Burns

1 mentions · Chris Ryan▶ 1:08:30IMDb ↗Lb ↗

Paul Bellany

1 mentions · Craig Horlbeck · Known for Stardust▶ 1:21:16IMDb ↗Lb ↗

Paul Thomas Anderson

1 mentions · Bill Simmons · Known for Punch-Drunk Love, Licorice Pizza, There Will Be Blood▶ 11:43IMDb ↗Lb ↗

Actors Referenced (57)

Pat Benatar

21 mentions · Bill Simmons, Chris Ryan · Known for The Italian Job▶ 8:51IMDb ↗Lb ↗

Helen Slater

17 mentions · Bill Simmons, Chris Ryan · Known for Ruthless People, City Slickers▶ 9:53IMDb ↗Lb ↗

Hubie Kerns Jr.

17 mentions · Bill Simmons, Chris Ryan · Known for The Island▶ 8:36IMDb ↗Lb ↗

Anthony Pyatt

12 mentions · Bill Simmons, Chris Ryan, Craig Horlbeck▶ 6:29IMDb ↗Lb ↗

Christian Slater

8 mentions · Bill Simmons, Chris Ryan · Known for Very Bad Things, True Romance, Robin Hood: Prince of Thieves▶ 4:23IMDb ↗Lb ↗

Billy Idol

6 mentions · Bill Simmons, Chris Ryan, Craig Horlbeck · Known for The Wedding Singer, Speed▶ 31:36IMDb ↗Lb ↗

Peter Coyote

6 mentions · Bill Simmons, Chris Ryan, Craig Horlbeck · Known for A Walk to Remember, Patch Adams▶ 4:27IMDb ↗Lb ↗

Barry Tubb

4 mentions · Bill Simmons, Chris Ryan · Known for Top Gun, The Legend of Billie Jean▶ 59:27IMDb ↗Lb ↗

Kid Cudi

4 mentions · Bill Simmons, Chris Ryan · Known for The Harder They Fall, Don't Look Up, Need for Speed▶ 21:36IMDb ↗Lb ↗

Lou Reed

4 mentions · Bill Simmons · Known for Blue in the Face▶ 1:07:09IMDb ↗Lb ↗

Rick Baker

4 mentions · Bill Simmons · Known for Planet of the Apes, Men in Black▶ 11:56IMDb ↗Lb ↗

Karl Malone

3 mentions · Bill Simmons · Known for Soul Plane▶ 20:51IMDb ↗Lb ↗

Writers Referenced (5)

Matthew Robbins

2 mentions · Bill Simmons · Known for Guillermo del Toro's Pinocchio▶ 15:39IMDb ↗Lb ↗

Noah Baumbach

2 mentions · Chris Ryan, Bill Simmons · Known for The Squid and the Whale, Marriage Story▶ 27:11IMDb ↗Lb ↗

Dominique Piat

1 mentions · Bill Simmons · Known for French Kiss▶ 1:11:35IMDb ↗Lb ↗

Paul Schrader

1 mentions · Bill Simmons · Known for First Reformed, The Card Counter▶ 1:11:47IMDb ↗Lb ↗

Roger Ebert

1 mentions · Bill Simmons▶ 27:29IMDb ↗Lb ↗