The Rewatchables

‘Two for the Money’ With Bill Simmons, Chris Ryan, and Cousin Sal

November 25, 2025

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  • The 2005 sports thriller ‘Two for the Money’ is viewed as perfectly capturing the pre-internet era of disingenuous sports touting via 1-900 numbers, which the hosts recall fondly. 
  • Matthew McConaughey's performance is considered perfect for the role, showcasing a fun, charismatic energy that holds up against Al Pacino's scenery-chewing, marking a key point in his career trajectory before his later resurgence. 
  • The movie's release timing (Columbus Day weekend) and its reliance on outdated sports gambling culture (touting over analytics) make it feel slightly dated, though its core mentor/fast-riser dynamic remains highly rewatchable. 
  • The 2005 setting of 'Two for the Money' is highlighted by dated references like the nascent internet, the illegality of sports betting in most states, and the prevalence of 900-number hotlines. 
  • Al Pacino's character, Walter, is interpreted as being obsessed with replacing his own sexual vitality through Matthew McConaughey's character, Brandon Lang, making the film a psychological study of vicarious living. 
  • Jeremy Piven's performance as Jerry Sykes is frequently compared to his role as Ari Gold in *Entourage*, suggesting a lack of range or a deliberate choice to lean into that persona. 
  • The central, often overlooked, dynamic of the movie 'Two for the Money' revolves around Walter's obsession with replacing himself with Brandon sexually, rather than just the sports gambling aspect. 
  • Al Pacino's performance is cited as the primary reason the movie remains entertaining and rewatchable, elevating it beyond its initial perception as a joke. 
  • The hosts suggest that 'Two for the Money' would have benefited from a larger scope, perhaps leaning into a 'Wolf of Wall Street' style frenzy, or being released outside of peak football season. 

Segments

Initial Greetings and Context
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(00:00:46)
  • Key Takeaway: The episode of The Rewatchables features Bill Simmons, Chris Ryan, and Cousin Sal revisiting the 2005 sports thriller ‘Two for the Money’.
  • Summary: The hosts greet each other, noting the taping occurred shortly after the Eagles lost 21-0 to the Cowboys. Cousin Sal notes his relative infrequency on the podcast, last appearing for Back to the Future Part II. The episode title confirms the focus is on gambling, aligning with the show’s recurring theme of ‘Gambling Again’.
The Sports Touting Phenomenon
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(00:02:38)
  • Key Takeaway: The movie’s 2005 release on Columbus Day weekend is questioned, leading to a deep dive into the 1990s sports touting industry.
  • Summary: The hosts recall the era of 1-900 sports advisors like Stu Feiner and Jack Price, whose unintentional comedy was only appreciated by those watching at the time. They detail the ‘sucker list’ scam where touts would call individuals, giving winning picks to a shrinking pool of people until they paid for the ’lock of the year.’ This system operated in a legal gray area, similar to other 1-900 services of the 1990s.
Post-Rounders Sports Content Era
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(00:03:25)
  • Key Takeaway: ‘Two for the Money’ belongs to a post-Rounders wave of sports content trying to capture the gambling/sports world, though it was shot cheaply.
  • Summary: The film is categorized among other late 90s/early 2000s sports content like Tilt, Playmakers, and Friday Night Lights. Unlike larger productions, this movie was largely shot in one office, relying heavily on USFL highlights due to difficulties securing rights for major league footage, resulting in generic, non-descript jerseys.
DNA Comparisons and Touting Focus
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(00:05:00)
  • Key Takeaway: The movie shares DNA with Rounders and Jerry Maguire but specifically focuses on the culture of sports touting, which aged both well and poorly.
  • Summary: The film captures the specific, often mythological advice given by 90s sports advisors, which listeners like Sal and his friend Jeff found funny before realizing the scam. The movie’s depiction of touting is contrasted with modern sports betting, noting that if someone truly had an edge, they would bet themselves rather than sell advice.
McConaughey’s Career Trajectory
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(00:16:51)
  • Key Takeaway: ‘Two for the Money’ falls within McConaughey’s ‘fallow period’ (2003-2008) between his initial A-list run and his later critical resurgence.
  • Summary: Between 2003 and 2008, McConaughey starred in several B-minus movies like Sahara and Failure to Launch, suggesting Hollywood temporarily lost faith in his leading man status. The hosts note that he was likely too famous for Kimmel’s show early on but became accessible by 2005, before his career was dramatically revitalized by Dallas Buyers Club and True Detective.
Pacino’s Performance and Wisdom
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(00:22:58)
  • Key Takeaway: Al Pacino’s performance in this film is considered a high point in his early 2000s renaissance, showcasing his ability to play off McConaughey without overshadowing him.
  • Summary: Pacino is noted as having 14 Rewatchables appearances, placing him second all-time among actors discussed. His character, Walter Abrams, delivers memorable lines about certainty and the high of gambling being the moment before the bet. The hosts observe that this film represents the tail end of Pacino’s era where he could plausibly play a character in his 60s with the energy seen in Scent of a Woman.
Most Rewatchable Scenes
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(00:30:44)
  • Key Takeaway: Key rewatchable moments center on McConaughey’s transformation, Pacino’s intense monologues, and the satirical depiction of the sports advisor show.
  • Summary: The hosts select the football preamble, Pacino’s hard sell to Brandon, Brandon practicing his John Anthony voice, and Pacino’s speech at the Gamblers Anonymous meeting as top scenes. The scene where Walter tells the GA meeting attendees they are all ’lemons’—not addicts, but personally bad gamblers—is highlighted as particularly brilliant.
Gambling Content Saturation Today
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(00:42:13)
  • Key Takeaway: Genuine, widespread fame for a sports picker like Brandon Lang is unlikely today because modern sports betting markets have near-perfect efficiency and information parity.
  • Summary: The hosts argue that the margins for easy wins that existed in the 90s are gone due to data, AI, and widespread knowledge of analytics (like OBP in baseball). Today, the only real edge might be in futures betting, as current odds are too tight for a single personality to consistently beat the market and gain mainstream fame solely through picks.
2005 Relics and Internet Allusions
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(00:49:43)
  • Key Takeaway: The movie features dated references like allusions to the internet’s impending arrival and the existence of sports advisor shows, which are now obsolete.
  • Summary: The hosts identify fax machines and vague references to the internet as markers of the 2005 setting. They note the obsolescence of the sports advisor shows featured in the film. A specific joke referencing Donald Trump’s hair is also pointed out as a period detail.
900 Number Job Details
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(00:51:55)
  • Key Takeaway: John Anthony’s job involved working for a 900 multimedia company in Las Vegas, specifically promoting a hotline related to Jessica Simpson trivia.
  • Summary: The hosts clarify Brandon Lang’s (John Anthony’s) job involved promoting a 900 number, which could cover gambling or celebrity content. Brandon was specifically tasked with getting people to call a Jessica Simpson trivia hotline. The difficulty of explaining such a job in that era is noted.
What Aged Best: Character Traits
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(00:52:48)
  • Key Takeaway: Al Pacino’s line describing another person’s mouth as a ’toilet’ is cited as a line that has aged exceptionally well.
  • Summary: Pacino’s character being based on the real-life Stu Finer, who is still active, is considered a great element that ages well. Pacino’s aggressive dialogue, specifically the ’toilet’ metaphor, is praised for its unique impact. Walter’s portrayal of family dysfunction and McConaughey’s physique are also listed as elements that hold up.
Piven’s Ari Gold Performance
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(00:54:20)
  • Key Takeaway: Jeremy Piven’s character felt like a direct continuation of his Entourage persona, Ari Gold, simply transplanted to a 900 hotline setting.
  • Summary: Piven’s role is described as playing Jerry Sykes as Ari from Entourage but working for a 900 hotline, suggesting he may have just finished filming an Entourage season. The hosts suggest Ari Gold would have been a better name for a tout service character. Piven’s performance is seen as lacking range by repeating the established character.
Movie Identity Changes and Hair
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(00:55:23)
  • Key Takeaway: Slicking back hair is identified as a common, yet often temporary, movie trope for signifying a character’s identity shift, often toward becoming dangerous or a villain.
  • Summary: The act of slicking back hair is highlighted as a specific cinematic identity change, referencing examples like Miami Vice. The hosts joke about adopting McConaughey’s look for the next phase of the podcast. Kevin Chapman’s role as a recognizable ’that guy’ actor is also praised.
Food/Drink and Cinematics
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(00:56:56)
  • Key Takeaway: The $1,000 bottle of wine and the use of the Monday Night Football theme song are the best uses of food/drink and music, respectively.
  • Summary: The $1,000 bottle of wine and Pacino cleaning up a dessert are noted for food/drink. The inclusion of the Monday Night Football theme song brings the hosts significant joy. The scene where Walter watches Brandon kiss Russo on the steps is cited as a moment where any music would have worked.
Worst Aged Elements: Medical and Gambling Eras
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(01:03:10)
  • Key Takeaway: The casual depiction of characters having minor heart attacks at work, taking a pill, and immediately recovering is the element that has aged the worst.
  • Summary: The ease with which characters recover from cardiac events by taking pills is deemed unrealistic and poorly aged. The entire era of sports gambling depicted—relying on bookies, 900 lines, and advisor shows—is considered ancient history compared to modern legalized betting. The film’s depiction of the scale of the illegal betting operation is also questioned.
Title Meaning and Betting Terminology
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(01:06:12)
  • Key Takeaway: The hosts collectively agree that the movie title ‘Two for the Money’ is confusing, suggesting it might relate to the betting term ’two for the show, three to get ready’ or simply mean two partners in business.
  • Summary: The hosts express confusion over the meaning of ‘Two for the Money,’ noting it doesn’t clearly align with betting terminology like ‘money line’ or ‘parlay.’ They reference the common phrase ’two for the show, three to get ready’ as a possible, though vague, connection. The title is ultimately deemed a poor choice.
Hottest Take: Remake Concept
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(01:07:04)
  • Key Takeaway: The hottest take suggests the movie should be remade as a period piece focusing on the ‘Wild West’ of sports gambling before legalization, potentially grounding it with real NFL teams and footage.
  • Summary: The current film fails because it takes the existence of sports advisors for granted without exploring the pre-legalization era more deeply. A remake could explore the ‘cowboys on the range’ aspect of selling picks in the wild west of betting. Using real NFL teams and games, rather than fictionalized ones, would have added grounding.
Best Giftable Pacino Moment
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(01:15:23)
  • Key Takeaway: Al Pacino’s line, ‘I’m gambling again,’ is identified as his most giftable moment, superior to his iconic scenes in Heat or The Godfather Part III.
  • Summary: The hosts argue that Pacino’s ‘I’m gambling again’ line from Two for the Money should be a massive meme or GIF, given its relevance to recurring betting behavior. They compare its potential impact favorably against his famous moments in Heat and The Godfather Part III. They suggest the podcast itself should popularize this specific GIF.
Worst Decision: Sykes Quitting
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(01:16:17)
  • Key Takeaway: Jerry Sykes quitting his complex 42-variable betting system after only a few rough weeks represents the worst decision in the film.
  • Summary: The decision by Sykes to abandon his detailed system after minor losses is deemed a poor choice, as he had invested significant time into it. The hosts speculate Sykes might have ended up working in analytics for a low-level team like the Buffalo Sabres. The film’s use of real USFL footage from the mid-80s is noted as factual research.
Unanswered Questions on Finances
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(01:27:02)
  • Key Takeaway: Walter’s ability to spend lavishly on surveillance, gifts, and entertainment for Brandon while supposedly being bankrupt raises significant financial inconsistencies.
  • Summary: The hosts question how Walter, who appears to be in debt, can afford expensive items like a car, Cartier, and $5,000 hookers to boost Brandon’s confidence. They note that Brandon only received 5% ($100,000) of a $2 million win, suggesting much of his lifestyle might also be on credit provided by Walter. The film’s central conflict is reinterpreted as Walter trying to replace himself sexually with Brandon.
Walter’s Sexual Obsession
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(01:38:59)
  • Key Takeaway: The core motivation for Walter’s character arc in ‘Two for the Money’ is his desire to replace himself with Brandon sexually, evidenced by him setting up McConaughey with his wife.
  • Summary: Walter is portrayed as being obsessed with the sexual vitality of the younger man, essentially gambling his wife to feel relevant. This dynamic is the underlying rush for Walter throughout the film. The discussion notes that the movie’s ending focuses oddly on Walter and Tony’s relationship status if viewed only through the surface plot.
Memorabilia Choices
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(01:40:06)
  • Key Takeaway: Cousin Sal would choose Jeremy Piven’s distinctive hair as his desired piece of memorabilia from ‘Two for the Money’.
  • Summary: Sal expressed a desire for Jeremy Piven’s hair, stating he would wear it every Sunday night on ‘Guess the Lines.’ Chris Ryan opted for the algorithm/psych system, while another host chose McConaughey’s Sun Devil’s Jersey from the opening scene. The townhouse where the operation was run was also suggested as a piece of memorabilia.
Life Lessons and Double Feature
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(01:40:40)
  • Key Takeaway: A key life lesson identified is that ‘modesty is not a virtue, it might be a vice,’ alongside the adage that ‘hot streaks go cold, cold streaks go hot.’
  • Summary: Chris Ryan suggested ‘Rounders’ as a double feature choice due to its similar voiceover style and thematic elements. Another suggestion was pairing ‘Devil’s Advocate’ first, followed by ‘Two for the Money,’ imagining Walter being saved in the latter film.
Who Won The Movie
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(01:41:22)
  • Key Takeaway: Al Pacino is declared the winner of the movie by multiple hosts because his hammy yet effective performance is what makes the film entertaining and rewatchable.
  • Summary: Pacino won the movie for Ebert, and his performance is credited with turning the film from merely ‘fine’ to entertaining. His over-the-top moments, like the fake heart attack in the airport, are what keep viewers coming back. McConaughey’s arc is seen as less pivotal, as he struggled with serious roles immediately following this film.
Rewatchability and Chemistry
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(01:42:10)
  • Key Takeaway: The hosts agree that ‘Two for the Money’ gains significant value upon rewatching, largely due to the strong chemistry between McConaughey and Pacino.
  • Summary: The episode title, ‘The Rewatchables,’ is validated as the movie improves on subsequent viewings, moving from a joke to a ‘pretty good’ film. The dynamic between the established star (Pacino) and the rising star (McConaughey) is highlighted as a great cinematic pairing, suggesting a modern remake should feature McConaughey and Glen Powell.
Alternative Plot and Release Timing
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(01:43:06)
  • Key Takeaway: The movie might have been more popular if it focused purely on sports betting syndicates rather than the touting/sexual advisor angle, and its release timing during football season hurt its box office potential.
  • Summary: The hosts speculate that focusing solely on pooling money to bet games could have resonated better with audiences. The film’s small scope, staying mostly in the Brooklyn Heights townhouse, prevented it from achieving a larger, ‘Wolf of Wall Street’-like feel. Releasing the movie in early March instead of during football season might have improved its performance.
Pronunciation Nitpick
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(01:44:27)
  • Key Takeaway: The hosts correct a common mispronunciation in the film, confirming that Brandon was correct in saying ‘Bruschetta’ instead of the corrected ‘Bruschetta.’
  • Summary: A nitpick was raised regarding the pronunciation of the Italian appetizer. Brandon correctly used the original pronunciation, ‘Bruschetta,’ but was corrected by others who used the more common, anglicized version, ‘Bruschetta.’