The Rewatchables

‘The Sting’ With Bill Simmons, Chris Ryan, and Sean Fennessey

September 30, 2025

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  • The reunion of Robert Redford and Paul Newman in *The Sting* is highlighted as a rare and highly successful example of a non-sequel pairing of major stars, a phenomenon that has become increasingly rare in modern Hollywood. 
  • The discussion posits that *The Sting* popularized the 'con man' movie genre in mainstream popular culture, setting a high bar for subsequent films in the genre due to its intricate plotting and fun execution. 
  • Robert Redford's career trajectory in the early 1970s, including *The Sting*, is noted as a period of immense power where he actively shaped his projects, often using his star power to select directors like George Roy Hill over the original writer-director choice. 
  • Paul Newman's performance in *The Sting* is uniquely layered because he spent his life hiding his alcoholism while playing a drunk character, creating an interesting dynamic. 
  • The film's enduring appeal is partly due to its aesthetic inversion: presenting a story about the Depression with characters who are impeccably dressed and maintain extreme coolness despite high stakes. 
  • The hosts identified the first meeting between Gondorf and Hooker as a highly rewatchable scene, showcasing the perfect jousting and affection between the two leads. 
  • The $500,000 take in *The Sting* is estimated to be worth over $9 million in 2020 dollars, highlighting the massive scale of the con. 
  • The hosts praise the script of *The Sting* as one of the great examples for aspiring screenwriters due to its structure and dialogue, despite some 1930s jargon being difficult to decipher today. 
  • The discussion concludes with the hosts debating potential future Redford Month selections, favoring *Three Days of the Condor* but acknowledging its better fit for a future '70s Conspiracy Month' theme. 

Segments

Physical Media Stacks
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(00:01:03)
  • Key Takeaway: Chris Ryan (CR) acquired approximately 40 Blu-rays from Tracy Letz’s doubles during a recent podcast recording session.
  • Summary: The hosts briefly discuss the accumulation of physical media among the crew. CR walked away from one episode with a large stack of Blu-rays provided by Tracy Letz, who had many duplicates. This leads to a lighthearted comment about doubling one’s stack.
Redford Month Kickoff
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(00:01:52)
  • Key Takeaway: The Rewatchables extended their tribute to Robert Redford into ‘Redford Month,’ starting with The Sting, the 1973 Best Picture winner.
  • Summary: The podcast is kicking off an extended tribute to Robert Redford, planning to cover five of his films. The Sting was chosen as the starting point due to its iconic status and Best Picture win in 1973. The hosts note the film also stars Paul Newman and Robert Shaw.
Newman/Redford Reunion Rarity
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(00:02:26)
  • Key Takeaway: The successful reunion of Paul Newman and Robert Redford in The Sting, following Butch Cassidy and the Sundance Kid, is noted as an exceptionally rare occurrence in film history.
  • Summary: The hosts examine how rare it is for two major stars to successfully reunite for a non-sequel film. They compare this pairing to other duos like Ben Affleck and Matt Damon, and Hanks/Ryan, concluding that the Newman/Redford pairing is historically significant. The discussion briefly touches on Will Ferrell and John C. Reilly as a modern equivalent.
Star Power Dynamics
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(00:05:08)
  • Key Takeaway: Paul Newman, despite Redford’s rising stardom, maintained a dominant presence on set, evidenced by Robert Shaw noting that crowds reacted much more strongly to Newman during filming.
  • Summary: The competitive nature of actors often prevents successful pairings from running back the chemistry immediately. Robert Shaw observed that during the filming of The Sting, the public reaction overwhelmingly favored Paul Newman. This dynamic is compared to modern pairings like Pitt and Clooney, and the hosts note that Redford’s charisma in this film is arguably his peak.
Modern Movie Star Equivalents
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(00:06:21)
  • Key Takeaway: The current film industry lacks the equivalent of the Newman/Redford star power dynamic, with modern pairings often occurring within IP-driven films like Dune: Part Two.
  • Summary: The hosts debate who the modern equivalent of Newman and Redford might be, suggesting Pitt and Clooney, but noting the age difference dynamic is different. They point to the showdown between Timothée Chalamet and Austin Butler in Dune: Part Two as a contemporary example of two major young stars sharing the screen. The conversation suggests that the industry no longer produces movie stars under 50 in the same way.
Con Movie Popularization
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(00:09:18)
  • Key Takeaway: The Sting is credited with significantly popularizing the ‘con man’ archetype in modern popular culture, despite the existence of earlier crime literature on the subject.
  • Summary: The film is considered a staple in the con movie genre, with Robert Redford noting that the script felt entirely new upon reading it. The hosts list other great con movies like House of Games and Focus. They debate whether the digital age has killed the possibility of effective, non-digital con movies.
The Triple Con Structure
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(00:21:03)
  • Key Takeaway: The Sting functions as a ’triple con movie’ because three separate deceptions—the assassination plot, the betrayal between Newman and Redford, and the fake federal agents—are happening simultaneously.
  • Summary: The film’s complexity lies in its layered deceptions, where nearly every character is lying to someone else. The hosts note that the film’s age helps the audience enjoy the journey without immediately suspecting every move, unlike modern thrillers. The casting of the waitress (Selena) is praised for making her appear mundane until her true role as an assassin is revealed.
Newman’s Career Trajectory
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(00:23:19)
  • Key Takeaway: The Sting marks the transition point where Paul Newman moved from his earlier roles into his mid-70s era, characterized by a slightly grayer look and a shift toward films like Slap Shot and The Verdict.
  • Summary: The hosts review Newman’s filmography leading up to The Sting, noting he was in a slump after Butch Cassidy. The original script reportedly required him to be older and fatter, but Newman negotiated for more screen time, including the iconic poker scene. His performance in The Sting is seen as the most charismatic of his career.
Redford’s Power and Shrewdness
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(00:26:55)
  • Key Takeaway: Robert Redford was instrumental in pioneering the modern use of star power in the 1970s, using his influence to shape projects, such as insisting George Roy Hill direct The Sting instead of the original writer, David Ward.
  • Summary: Redford is credited with helping invent the modern star system where an actor’s involvement guarantees a film’s success and runway. The making of The Sting involved Redford declining to let the writer direct, instead bringing in the established George Roy Hill. This shrewdness, while sometimes prickly, resulted in a string of great films.
Robert Shaw’s Explosive Career
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(00:35:27)
  • Key Takeaway: Robert Shaw delivered an incredible run of major films (The Sting, Jaws, The Taking of Pelham One Two Three) in just five years before dying prematurely at age 45 from causes related to heavy drinking.
  • Summary: Shaw was only 45 during The Sting, yet looked significantly older, a contrast to modern actors. He was known for intense behavior, including a legendary post-production bender with director George Roy Hill that ended with Shaw screaming at a ping pong opponent. Shaw was reportedly rivals with Sean Connery, feeling they were competing for similar roles.
1973 December Release Insanity
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(00:41:23)
  • Key Takeaway: December 1973 represents one of the greatest months in movie history, featuring the simultaneous release of The Sting, The Exorcist, Magnum Force, and Serpico.
  • Summary: The hosts list the staggering number of major films released in December 1973, including Fantastic Planet and The Wicker Man. George Roy Hill won Best Director over Lucas, Bergman, and Friedkin for The Sting. Robert Redford received his only acting nomination for this film but did not win.
Oscar Snubs and Domino Effect
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(00:42:26)
  • Key Takeaway: Jack Lemmon winning Best Actor for Save the Tiger over Al Pacino for Serpico created a domino effect where Pacino was subsequently denied an Oscar win until Scent of a Woman years later.
  • Summary: The hosts critique the 1973 acting awards, arguing Pacino should have won for Serpico. They note that Jack Nicholson also lost for The Last Detail that year, though he won two years later for One Flew Over the Cuckoo’s Nest. The discussion pivots to planning a future ‘Pacino Month’ for The Rewatchables.
Rewatchable Scenes and Con Mechanics
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(00:46:52)
  • Key Takeaway: The initial con where Luther demonstrates his pickpocketing skills on Hooker, and the subsequent poker scene where Newman hilariously cheats, are identified as the most rewatchable moments.
  • Summary: The hosts praise the scene where Hooker loses money at roulette, noting that while it establishes his compulsive nature, it seems unrealistic for a good gambler. They highlight Paul Newman’s comedic acting during the poker scene where he secures four jacks, noting that Newman’s real-life struggle with alcoholism adds an interesting layer to his performance of playing drunk.
Newman’s Drunken Acting Dynamic
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(00:50:07)
  • Key Takeaway: Paul Newman’s lifelong struggle with alcoholism informed his performance of being drunk in The Sting.
  • Summary: Newman reportedly drank 12 beers daily for 30 years, and the recurring physical action of dipping his face in cold water, seen in the film, was a real-life necessity for him. This created an interesting dynamic where he was playing drunk while having spent his life pretending he wasn’t. This technique is also noted as being used by Robert De Niro in Taxi Driver.
Rewatchable Scene Favorites
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(00:52:06)
  • Key Takeaway: The initial meeting between Gondorf and a hungover Hooker is considered a top rewatchable scene due to the perfect jousting and underlying affection between the two leads.
  • Summary: The poker scene was cited as a favorite for its inherent tension, but the first meeting between Newman’s Gondorf and Redford’s Hooker was highlighted as superior. In that scene, every line is perfect, and the dynamic establishes the uncertainty of whose movie it will ultimately be. The hosts noted the obvious affection despite the competitive nature of their initial interaction.
Most 1973 Elements
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(00:52:44)
  • Key Takeaway: The film’s aesthetic—snazzy dressing and cool demeanor amidst the Depression—is a defining, charmingly anachronistic element of its 1973 production.
  • Summary: The movie is set in 1936 but romanticizes the era, making the Depression seem charming in retrospect. The characters maintain extreme coolness despite high stakes, which is a tonal inversion that makes the film work. Robert Shaw’s appearance, looking much older than his actual age of 45, and the presence of payphones also date the film to its production era.
What Aged Best Discussion
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(00:55:57)
  • Key Takeaway: The film’s inversion of its setting—presenting cool characters in a desperate time—is what has aged the best, influencing later heist films like Ocean’s Eleven.
  • Summary: The movie’s success lies in its presentation of characters who are impeccably dressed in three-piece suits and fedoras while navigating an anxious, high-stakes situation without showing visible stress. The hosts noted that the film’s style directly influenced Ocean’s Eleven. Other elements that aged well include pickpocketing as a cinematic device and the inclusion of train trips where tension is expected.
The 1973 Oscars Anecdotes
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(01:04:46)
  • Key Takeaway: The 1973 Academy Awards ceremony, where The Sting won Best Picture, was notably unpolished, featuring a streaker and a disoriented Al Pacino.
  • Summary: Liz Taylor presented Best Picture and was visibly flustered by a streaker, while Al Pacino, nominated for Serpico, reportedly took a Valium thinking the ceremony was shorter and was unprepared when the time came to present. The hosts noted that the Oscars felt less polished then, with attendees likely being intoxicated before arriving.
Award Category Winners
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(01:09:00)
  • Key Takeaway: Marv Hamlisch won three Oscars for The Sting, including Best Scoring Adapted Score, a category that no longer exists due to rules against adapting previously used music.
  • Summary: The ‘Wonderful Edit Willie’ award went to William Reynolds for his editing, which softened the gritty content with wipes and iris transitions, similar to The Godfather. Harold Gould, known for The Golden Girls, was voted the best supporting actor, and the carousel whorehouse was named the best scene-stealing location.
Redford’s Performance and Career Arc
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(01:19:04)
  • Key Takeaway: One host’s hottest take is that The Sting is not among Robert Redford’s top ten performances, arguing he was too old for the role while Newman was too young for his.
  • Summary: The host believes Redford is better in films like Three Days of the Condor and The Way We Were, noting Redford often played younger than his actual age. Redford’s performance in The Sting and The Way We Were in the same year solidified his status as ‘first call’ actor, meaning he could greenlight any project he wanted.
On-Set Pranks and Star Power
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(01:21:39)
  • Key Takeaway: Pranks among major stars like Paul Newman and Robert Redford were considered cool in the 1970s but would likely be deemed workplace harassment today.
  • Summary: Newman once stole Redford’s Porsche on set as a prank, and Newman and director George Roy Hill engaged in ongoing pranks, including sawing a desk in half. The hosts lamented that this era of playful, elaborate pranks seems to have ended, possibly due to the influence of shows like Punk’d.
Con Mechanics and Extras
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(01:39:41)
  • Key Takeaway: The complexity of the fake wiretapping and the necessity of 20-30 extras in the betting parlor for the con’s success are noted.
  • Summary: The mechanics of the fake wiretapping setup are confusing to one host, but the necessity of at least 20 extras in the betting parlor for the con is confirmed. The hosts speculate on how the $500,000 take would be split among the participants.
Inflation and Future Projects
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(01:41:27)
  • Key Takeaway: The $500,000 payoff in The Sting equates to approximately $9.2 million to $11 million in 2020 dollars.
  • Summary: IMDB calculated that $500,000 in the 1930s is equivalent to about $9.2 million in 2020, with another host citing a figure closer to $11 million. The hosts briefly consider potential sequels, prequels, or Prestige TV shows based on the characters.
Oscar Wins and Script Quality
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(01:44:00)
  • Key Takeaway: The script for The Sting is widely considered one of the great screenplays, with Paul Newman noting only four words were changed during shooting.
  • Summary: George Roy Hill is credited for his direction, and the Best Screenplay Oscar win is highlighted as deserved due to the script’s structure. Newman reportedly stated that the script remained almost entirely intact from the drafts to the final film.
Doyle’s Golf Handicap
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(01:44:42)
  • Key Takeaway: Doyle’s golf handicap is speculated to be around 15, factoring in his big hitting but poor short game and tendency to cheat.
  • Summary: The hosts speculate on Robert Shaw’s character Doyle’s golf handicap, noting his powerful hitting but questionable short game and cheating habits, such as kicking the ball out of the rough. Doyle’s injury from a handball accident is mentioned as a potential factor affecting his play.
Memorabilia and Life Lessons
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(01:45:23)
  • Key Takeaway: The best piece of memorabilia would be Paul Newman’s wallet, and the best life lesson is that revenge is for suckers.
  • Summary: Hosts would want poker chips from the game or Lonigan’s wallet containing counterfeit money as memorabilia. The key life lesson derived is that one must keep the con going even after taking the money, meaning revenge is unnecessary and for suckers.
Double Feature and Redford/Newman
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(01:46:47)
  • Key Takeaway: The hosts decide Robert Redford won the movie over Paul Newman, and they agree that Newman and Redford should have made more films together, avoiding later weaker entries like Legal Eagles.
  • Summary: Redford is declared the winner of The Sting because he walks out ‘smelling like gold,’ though the pair’s two films together are considered perfect. They speculate on potential 1980s reunions, suggesting they could have played aging detectives.
Producer Craig’s Takeaways
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(01:51:05)
  • Key Takeaway: Producer Craig Horlbeck loved The Sting even more on rewatch, noting its success as a perfect commercial and critical hit filmed entirely on sets.
  • Summary: Craig Horlbeck, though absent, provided feedback confirming the film worked on him again, specifically forgetting the FBI was part of the con and that ‘Seleno in the diner’ was a setup. He praises the film as the best example of commercial and critical success, noting its cinematic quality despite being filmed entirely on sets resembling an Edward Hopper painting.
1930s Jargon and Nicknames
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(01:52:01)
  • Key Takeaway: The 1930s jargon in The Sting is so dense that phrases like ‘quill’ and ‘New York wheel’ are indecipherable without context, unlike modern slang.
  • Summary: Craig noted that many lines contain jargon like ‘Dookie,’ ‘quill,’ and ‘wheel’ (likely meaning a high roller or whale) that are completely opaque without context. The hosts lament the loss of creative nicknames like ‘Kid Twist’ in modern culture, contrasting it with the era of The Sting.
Redford Month Future
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(01:54:40)
  • Key Takeaway: The hosts hope to cover Three Days of the Condor for Redford Month, but acknowledge it might be better saved for a dedicated ’70s Conspiracy Month’ theme.
  • Summary: The most desired Redford film for the month is Three Days of the Condor, though its strong fit for a conspiracy theme presents a scheduling conflict. The hosts suggest a creative transition where the final Redford film could blend directly into the start of ’70s Conspiracy Month.'