The Rewatchables: ‘Sneakers’ With Bill Simmons, Kyle Brandt, and Joanna Robinson

Date: October 14, 2025
Podcast: The Rewatchables (The Ringer Podcast Network)
Episode: Sneakers (1992)

Episode Overview

In this episode, Bill Simmons is joined by Kyle Brandt and Joanna Robinson to discuss the 1992 tech-heist classic “Sneakers.” With the recent passing of Robert Redford, the trio dive deep into why the film is a sleeper favorite, the star-studded cast, and its surprisingly prescient take on hacking, surveillance, and paranoia in the digital age. Along the way, they debate the film’s curious legacy, dissect its “bad” title, and have a wide-ranging conversation covering everything from River Phoenix’s career to whether Robert Redford wore a wig.

Key Discussion Points & Insights

1. “Sneakers” as a Cult Classic

• Kyle Brandt:
  • Proclaims “Sneakers” as the most underrated movie of the 1990s:

    “I think Sneakers is the most underrated movie of the entire 1990s... charming, has some of everything—suspense, comedy, romance...people don't talk about it enough.” (02:23)

  • Describes the movie as “a password” among film fans: meeting another “Sneakers” fan feels like joining a secret club. (03:08)
• Joanna Robinson:
  • Agrees and finds joy in the film’s word-of-mouth status:

    “There's something I kind of like about that... It becomes this, like, password for people...you look like a genius when you show it to someone new.” (03:08)

• Bill Simmons:
  • Confesses he missed it when it came out in 1992, only appreciating it after multiple recent rewatches:

    “I watched this movie three times in the past month...they were so far ahead of the game.” (05:54)

  • Suggests it created a “cyber caper” genre. (10:00)

2. Why Doesn’t “Sneakers” Have a Larger Legacy?

• The Title & Marketing Problem:
  • All agree “Sneakers” is a terrible, misleading title and the poster only adds to the confusion—it’s neither about shoes nor clear in its premise.
    • Kyle: “I think it has a terrible title that is off-putting and confusing...” (07:08)
    • Joanna: “Terrible title, terrible poster, terrible tagline.” (07:39)
  • In the age of Google, it’s even harder to discover.
  • Alternate titles suggested: “Too Many Secrets,” “No More Secrets,” or even “Hackers,” (which ended up being used by a later, less appropriate movie). (08:08)

3. The Cast & the “Dad Movie” Vibe

• Redford, Poitier, River Phoenix, Dan Aykroyd, Ben Kingsley, Mary McDonnell, and cameo by James Earl Jones.
  • Joanna: “You have one of the biggest heartthrob stars [River Phoenix]... and he's just like the doofy Comic Relief guy.” (11:53)
  • Bill: “Redford is 56 in Sneakers. I have some thoughts about that...” (28:49)
• Strong consensus that Redford’s presence anchors the film, even if he’s too old for the role by modern standards.
• Bill (on Mary McDonnell): “It's a nothing part...but she makes it work.” (23:23)
• Comic and warm ensemble dynamic gives the film its rewatchable “hang-out” appeal.

4. Prescient Themes: Hacking, Paranoia, and Silicon Valley Before Its Time

• The film is lauded for foreseeing “the information age,” the rise of digital paranoia, and self-important Silicon Valley techies:
  • Bill: Quotes from Kingsley’s Cosmo character—

    “There's a war out there, old friend—a world war...and it's not about who’s got the most bullets...it’s about who controls the information.” (15:19)

  • Joanna: “This feels like one of the first Silicon Valley movies.” (15:57)
  • The chilling concept that “he who controls the information, controls the world” is tagged as way ahead of its time for 1992.

5. Structure & Genre-Bending

• Post-Cold War Heist, Cyber Caper, and Comedy Mash-Up:
  • The group emphasizes how “Sneakers” mixes genres: it’s a heist, a comedy, a paranoia thriller, and a sly post-Cold War victory lap over Russia.
    • Kyle: “It’s like the hacking movie, the paranoia movie, the comedy...” (10:12)
• The film’s complexity is credited to a script worked on for a decade, with a plot that “fits together so neatly like a puzzle.” (11:11)

Notable Quotes & Memorable Moments

• On River Phoenix:
  • Bill: “He was kind of the guy... what Leo became in the mid-90s.” (13:01)
  • Kyle: “Spielberg handpicks him as young Indiana Jones... all-time legacy character.” (13:31)
• On Cosmo and 90s Tech Fears:
  • Joanna: “Cosmo as this precursor for what the emotionally stunted men of Silicon Valley will do and control in the future...” (15:57)
• On the Movie’s (Unintentional) Legacy:
  • Joanna: “The cybersecurity world loves Sneakers. They're like, ‘Sneakers got it right, man.’” (19:54)
• On Redford’s ‘Hall of Fame Eye Narrower’ Skills:
  • Bill: “When his eyes narrow, you know the wheels are turning...” (43:22)

Important Timestamps for Segments

• [02:20] — Kyle Brandt makes his opening case for “Sneakers” as the most underrated film of the 1990s.
• [03:08] — Joanna Robinson describes the film’s cult “password” status.
• [05:21] — Bill Simmons confesses to discovering the film only recently.
• [07:08] — The trio trashes the film’s title and marketing.
• [10:00] — Bill: “Sneakers creates a new genre—the cyber caper.”
• [11:11] — Joanna: “It fits together so neatly, like a puzzle.”
• [15:19, 15:43] — Discussion of Cosmo's prophetic monologues about information warfare.
• [16:57] — WarGames as the spiritual predecessor and origin of Sneakers' writers’ research.
• [23:23] — Bill and Joanna assess Mary McDonnell’s role.
• [24:26] — Roger Ebert's (lukewarm) original review debated: "It's a borderline fuck you, Raj."
• [34:17] — Discussion of film's “dad movie” rating and lack of clear demographic.
• [40:47] — The Ben Kingsley/Cosmo reveal and villain motivations analyzed and affectionately mocked.
• [51:06] — James Earl Jones’ cameo celebrated.
• [67:46] — Joanna introduces the Matt Damon Eurotrip Award for most unexpected A-lister cameo.
• [70:03] — Ben Kingsley is declared the episode’s “weak link” for his accent, acting choices, and running.
• [77:15] — Alternate casting musings (would Kevin Costner have made a better lead?).
• [95:05] — The eternal comic power of “helium voice” jokes is debated.
• [110:20] — “Did Redford wear a wig?”—Simmons’ deep-dive unanswerable question.

The Rewatchables’ Signature Categories & Awards

Most Rewatchable Scene(s)

• The Redford vs. Kingsley “Cosmo reveal” and villain monologues ([40:47])
• The Scrabble hacking/Cracking “Setec Astronomy” anagram ([24:54])
• The final heist—crossing Cosmo's office ([52:10])
• James Earl Jones’ government suit cameo and the bizarro wish-granting ending ([51:06])

Most 1992 Thing About the Movie

• Redford’s “Natural” baseball jacket; Mary McDonnell’s feathered hair; chunky tech; computer-dating subplots ([53:34–54:43])
• Storing secret data in an answering machine; hacking as portrayed by Scrabble games ([56:27])

Best Aged Elements

• Score by James Horner (later adored by composer Nicholas Britell) ([62:39])
• Ensemble “hangout” energy; mix of comedy and smart plotting
• “Information paranoia” and Silicon Valley lampooning ([58:16])

Weak Link of the Film

• Ben Kingsley’s all-over-the-map accent and acting choices as Cosmo—plus his bizarre run, called “The Steven Seagal Award” ([69:53–70:18])

Hottest Take

• Joanna: “This is Redford’s best film of the 1990s and his last truly great role.” ([80:45])
• Kyle: Bishop’s tense office-crossing is more impressive than anything Ethan Hunt does in Mission Impossible. ([81:23])

Modern Lens / “What’s Aged Worst”

• Clunky title/marketing and limited modern reach for younger audiences
• Aging tech and hacker tropes outpaced by newer thrillers like Enemy of the State and Ocean’s Eleven ([120:07])
• Casting: Redford “obviously too old for the role but who cares?” Kingsley too young for his character, and River Phoenix just "the doofy Comic Relief guy" ([11:53])

Recapping & Recasting

• Alternate Cosmo: Willem Dafoe, Jon Voight, William Hurt
• Alternate lead: Kevin Costner floated as a strong “what if”

Half-Assed Internet Research

• The real origins of the hackers (“phone phreakers”) and how Jobs/Wozniak were early real-world versions ([90:39–91:04])
• The “Natural” jacket is not the same as in "The Natural"—but it’s fanservicey close ([54:09])

Fun and Bizarre Observations

• Extended riff on whether Redford wore a wig in his later career ([112:26])
• Praise for the San Francisco Bay Area as a cinematic backdrop ([88:09])
• Does anyone in 2025 still play Scrabble?—debated ([78:05])
• “Helium-voice” jokes as timeless comic gold ([95:17])
• The “Dad Movie” genre affirmed, with field-of-dreams/Tin Cup/Sneakers as key touchstones ([33:32])

Concluding Thoughts

• All agree: “Sneakers” is a good hang, a smart puzzle of a movie, and a comfort film—anchored by Redford’s movie-star charisma and a peerless, eclectic supporting cast.
• The film may not be as universally known as its contemporaries, but among its fans, it’s legendary for its blend of comedy, tech paranoia, and 90s charm.
• A new generation (and pod listeners) are encouraged to seek it out—armed with the password: “Setec Astronomy.”

For Further Exploration

• Double Feature Suggestions: “WarGames” (1983), “Patriot Games,” “Hackers”
• Segment Timestamps:
  • [02:20] – Opening Case for the Movie
  • [07:08] – Title/Poster Critique
  • [11:11] – Script & Puzzle Structure
  • [15:19] – Cosmo’s Quotes
  • [51:06] – James Earl Jones' Scene
  • [69:53] – Ben Kingsley Roast
  • [95:17] – Helium Voice Bit
  • [120:07] – Craig’s Gen Z Critique

End of Summary.
For classic movie buffs, “Sneakers” remains a rewatchable password into a certain kind of club. This episode is your invitation.