The Rewatchables: ‘The Sting’ (1973)

Host: Bill Simmons
Guests: Chris Ryan (CR), Sean Fennessey
Date: September 30, 2025
Film Discussed: The Sting (dir. George Roy Hill, starring Paul Newman & Robert Redford)

Main Theme & Purpose

The Ringer’s Bill Simmons, Chris Ryan, and Sean Fennessey revisit and dissect The Sting (1973), the iconic con-man classic starring Robert Redford and Paul Newman, as the first installment of "Redford Month" on The Rewatchables. The conversation dives deep into the film’s legacy, genre influence, casting dynamics, production folklore, and place in movie history, all through their signature blend of trivia, personal anecdotes, and sharp wit.

Key Discussion Points & Insights

1. The Magic of the 'Get the Band Back Together' Casting

• The episode opens by reflecting on Redford and Newman, reunited here after Butch Cassidy and the Sundance Kid. Such team-ups are noted as rare and nearly mythic.
  • Bill: "Has there ever been a more successful get the band back together non-sequel?" (02:03)
  • After running the table on other iconic duos, the guys agree it's more elusive in modern Hollywood—perhaps only rivaled by pairs like Will Ferrell/John C. Reilly, or Sandler/Barrymore.

2. Movie Star Dynamics: Newman vs. Redford

• Discussion on Newman’s enduring aura vs. Redford’s meteoric rise in the early ‘70s.
  • Bill (on Robert Shaw’s observation): "Everyone was just going nuts for Newman. And then they asked what about Redford? And he was like, nah, this is really Newman." (04:36)
• They riff on modern analogies: Clooney/Pitt, Chalamet/Leo, and how Hollywood no longer has these under-50 titans.

3. Defining & Ranking the 'Con Movie'

• The team debates whether The Sting is the genre’s ur-text—a benchmark for all subsequent con films.
  • Chris Ryan: "When [Redford] read the script, he was like, there has never been a movie in this world before." (08:43)
• They track the genre’s legacy: from Ocean’s 11 to Usual Suspects, Trading Places, Focus, and House of Games.

4. Why Is the Classic Con Movie Difficult Today?

• Technology has rendered "pure" cons harder to write (and believe).
  • Chris: "So much of, like, what we would consider conning or a con 30 or 40 years ago is now phishing emails..." (15:29)
• The broader point: movie audiences are savvier, and real-world scams are less cinematic and more insidious than the “fun” cons of The Sting.

5. Moral Codes of Con Men and the Performance of Lying

• The film’s romanticized confidence men are compared with today’s scams.
  • Chris: "A big part of being a good con man is never breaking, never reveal..." (18:25)
  • Discussion of “good” vs. “bad” lying and poker as the art of bluffing.

6. Breaking Down the Film: Structure and Scenes

• Triple Con Structure: The plot weaves three layers of deception—Hitwoman Seleno, Redford/Newman double cross, the faux Feds.
  • Bill: "The hardest thing to pull off with the audience is that I have to be surprised at the end..." (20:08)
• Multiple scenes are dissected:
  • Initial grifts (the pants switch)
  • The legendary poker scene on the train
  • The diner hitwoman twist
  • The intricate, nearly meta construction of the final con

7. Best Picture 1973: Did The Sting Deserve It?

• The team questions The Sting’s win over American Graffiti and The Exorcist.
  • Sean Fennessey: "The Exorcist not winning is a goddamn nightmare." (39:48)
  • They marvel at December 1973’s stacked theatrical releases.

8. Behind the Scenes: Power Moves and Production Anecdotes

• Redford’s Emergence as Hollywood Power Broker:
  • Controlled director/producer decisions, shaped careers, sometimes at the cost of writers/directors (26:00-28:15).
  • Julia Phillips’ stories: Constant lateness on set, Newman’s frustrations, prank battles (87:36-88:12, 79:30-80:24).

9. Supporting Cast and Oscars

• Homage to Robert Shaw's electric presence and the supporting bench (Eileen Brennan, Ray Walston, Charles Durning, etc.), the enduring cultural impact of Scott Joplin's "The Entertainer," and The Sting's seven Oscar wins.

Notable Quotes & Memorable Moments

• On Redford's Proto-Hollywood Influence (26:00):
  "Redford is in the running for maybe inventing [the modern movie star as producer]." — Bill

• On the genre’s legacy (12:07):
  "You don't get 'Usual Suspects' without this. You don't get the lingo." — Chris Ryan

• On modern scams (15:29):
  "So much of what we would consider conning or a con 30 or 40 years ago is now phishing emails... " — Chris Ryan

• On the iconic poker scene (24:45):
  "That nine minutes, he's just cooking. All-time cooking." — Bill Simmons (on Newman)

• On the necessity of re-watching (33:11):
  "If you forget a few plot moments, it’s more fun. This movie's best seen every 10 years." — Chris Ryan

• On the lack of today's ‘sexy cons’ (56:27):
  "Fixing races, counterfeit money, cheating at poker ... just seemed way easier to do once upon a time ..." — Bill Simmons

• On Star Power (89:07):
  "This would be a good championship belt to figure out ... Redford is now after The Sting first call for like, I would say three, four years." — Bill Simmons

Timestamps for Key Segments

• Opening: Physical media chat & Redford Month intro (00:00–01:00)
• Redford & Newman: Revisiting legendary pairings (01:53–04:36)
• Modern star comparisons/Why we lack new Newmans (05:25–07:04)
• Defining “con man” movies & The Sting’s genre impact (08:24–13:10)
• How con movies have changed (digital age & culture) (15:19–17:19)
• The ethics/performance of lying and cons (18:10–19:19)
• Film structure: Triple cons, Seleno, fake Feds, poker (20:00–21:41)
• Oscars, 1973: The Sting vs. Exorcist/American Graffiti (39:38–41:05)
• Behind the scenes: Redford’s power, production lore (26:00–28:41)
• Odes to supporting cast: Eileen Brennan, Shaw, etc. (37:38–38:07, 34:34–36:41)
• Rewatchable scenes: Pants switch, poker, diner twist (45:53–51:44)
• Modern analogues & what’s aged well or not (54:07–56:48)
• Closing categories & playful hypotheticals (70:37–80:24)
• Final verdicts: Who won the movie? Legacy? (105:41–106:05)
• Producer Craig reflects: why the movie holds up (109:37–111:41)

Categories Explored (Condensed Highlights)

• Most Rewatchable Scene:
  Poker game on the train ("All-time cooking" – Bill, 24:45), Seleno twist, initial pants switch.

• Best 1973 Thing About The Movie:
  Robert Shaw looking 20+ years older, payphones, nostalgia for “roaring” crimes.

• Best Con Movies: The Sting, Ocean's Eleven, Focus, Catch Me if You Can, Trading Places, House of Games, etc.

• Weak Link:
  Consensus: Pointless hitmen Colson/Sullivan subplot, and wish for a 1930s 'babe.'

• Best Supporting:
  Eileen Brennan, Dana Elcar (FBI agent), Jack Kehoe (Kid Twist), Lonigan’s silent henchman.

• Who Won the Movie?
  Split between Newman (for the iconic poker scene) and Redford (star power, career arc).
  But there’s a strong argument for director George Roy Hill as well.

Flow, Tone, and Atmosphere

The tone is irreverent and conversational with jokey asides, pop culture riffs, and deep trivia drops. Bill, Chris, and Sean balance fanboy love (for the stars, script, and vibes) with sharp criticism (on pacing, 1973’s Oscar choices, and genre limitations). Anecdotes about Hollywood, Newman's drinking, and Redford's set behavior abound.

Final Takeaways

• The Sting is held up as a model of star chemistry and genre-defining caper construction, full of sly period detail and a swindler’s sense of fun.
• Its legacy, both in con movie mechanics and the mythology of “movie star power,” is unassailable, even as contemporary tastes and technology have shifted the genre.
• While not as radical or “important” as its Best Picture competition (The Exorcist, American Graffiti), The Sting remains a crowd-pleasing, technically masterful rewatch staple.
• The hosts agree: watch every 10 years, forget some twists, and let yourself be taken all over again.

Additional Resources

• For a full transcript, see The Ringer’s archives or YouTube channel for this and other Rewatchables episodes.
• The Sting currently streaming and occasionally in theatrical re-release.