The Rewatchables: 'Two for the Money'

Host: Bill Simmons
Guests: Chris Ryan, Chris Vannini, Cousin Sal (Salvatore Anthony), Craig
Date: November 25, 2025

Episode Overview

The Rewatchables crew dives into Two for the Money (2005), the under-the-radar sports gambling drama starring Matthew McConaughey and Al Pacino. The panel explores the film as a time capsule of pre-legalized sports betting, a vehicle for rowdy performances, and a weirdly personal snapshot of a once-seedy side of sports culture. They reminisce about the era of 900-number touts, reflect on McConaughey’s career trajectory, debate the film’s rewatchability, and question the logic (and hairlines) behind its characters. True to The Rewatchables spirit, the episode is packed with nostalgia, raucous sidebars, and sharp analysis of what makes this movie endure on cable.

Key Discussion Points & Insights

1. The Golden Era of Sports Gambling Content

[03:22-06:46]

• The guys position Two for the Money as a post-Rounders, pre-legalized gambling artifact, when touts and 900 numbers were still king.
• Chris Ryan recalls watching the “Sports Advisors” and the sheer entertainment value of characters like Stu Finer and Jack Price, even before the rise of ironic internet fandom.
• Sal shares a personal story about being suckered by a tout’s scam in college, underlining the manipulative, "boiler room" nature of the industry.

"What kind of idiot gives $400 to a total stranger?"
— Salvatore Anthony, recounting a tout’s brutal retort to his college friend Harry [09:42]

2. Movie Context: Why Did Hollywood Make This?

[12:00-14:45]

• The 2000s were awash in sports movies, but Two for the Money stands apart by focusing on sports betting touts, not athletes or gamblers themselves.
• The hosts riff on the “mentor-fast riser” archetype (Wall Street, Devil’s Advocate, Training Day), and how this film injects it into the world of sports picks.
• Sal notes the oddness of the release date: “Why would they release this movie Columbus Day weekend? Just dead for sports.” [01:30]

3. Touting vs. Betting: The Lost Subculture

[05:00-07:45]

• The movie captures a uniquely '90s form of sports gambling—tout services—where customers pay for picks but never directly bet.
• Chris: "The best part of this movie is it captures exactly what that was like. I wish it had done more." [06:29]

4. Real-Life Parallels and Scam Exposés

[08:20-09:44]

• Panel recounts how touts were exposed as frauds by media (notably Rick Reilly in SI), and how naive they themselves were as young sports fans.
• Sal describes how touts would split a list of callers and guarantee half of them wins, creating a false image of prediction accuracy.

5. McConaughey’s Career in Transition

[17:08-21:04]

• The film lands in McConaughey’s “pre-McConaissance” lull (“Failure to Launch,” “Sahara”), before he reinvented himself with Magic Mike and Dallas Buyers Club.
• Chris quotes from his own 2005 column, wondering: "Why do I root for him in every movie?...Doesn't it feel like his career should have been better? He's the Jimmy Jackson of Hollywood." [18:46]

“If you threw this movie at him today or 10, 20 years ago, he'd still do it…My brother was a tout…He had a tout service…27 and 0, then everybody hated him as soon as he lost.”
— Sal relaying McConaughey’s research into the role [20:05]

6. Pacino: The Grouchy Gambler King

[23:51-29:11]

• The panel celebrates Pacino chewing scenery, channeling echoes of Heat, Scent of a Woman, Devil’s Advocate, and even Dog Day Afternoon.
• Pacino’s character, Walter Abrams, is dissected as both mentor and deeply broken—a gambling, sex, and paternal figure wound together.
• Memorable lines:
  • “Modesty’s not a virtue. Might be a vice.” [25:04]
  • “You lactose intolerant fuck.” [25:24]
  • “You’re selling certainty in an uncertain world.” [25:12]

7. The Absurdity & Camp of Sports Betting Movies

[34:34-47:58]

• From shirtless McConaughey workout montages to the Sports Advisors’ faux TV set, the movie serves as a time capsule of male bravado and over-the-top “systems.”
• The guys revel in the gambler’s anonymous “lemons” speech—a highlight for memorable Pacino monologues [47:25].
• The “psych system”—a parody of touts’ pseudo-analysis—is dissected and affectionately mocked.

8. What’s Aged (Best/Worst), and the Shifts in Gambling Culture

[49:50-54:00; 63:13-65:12]

• What’s aged best: the dead genre of sports tout shows, Pacino's performance, and the nostalgia for “analog gambling” before everything went digital.
• What’s aged worst: the whole premise—nobody calls 900 lines anymore, and sports betting is fully legalized, digitized, and data-driven.
• Debate over title: "I still don’t understand it now, how we ended up with this title…what does Two for the Money mean?” [66:13]

9. Rewatchable Scenes

[30:40–48:00]

• Noteworthy, memorable scenes:
  • McConaughey’s college QB injury [31:12]
  • The “lemons” speech at Gamblers Anonymous [34:34]
  • Sports Advisors TV show parodies [13:49 & 34:59]
  • Brandon’s hot streak montage and subsequent cold spell

“Look, you give me McConaughey playing quarterback in college with crazy long hair…that’s rewatchable.”
— Chris Ryan [31:12]

“I love every scene with the Sports Advisor show...I wish there was more.”
— Chris Ryan [33:09]

Notable Quotes

• “The best advice I ever heard: ‘What kind of idiot gives $400 to a total stranger?’”
  — Sal [09:44]

• “This movie is probably six, seven years too late.”
  — Chris Ryan [10:27]

• “Mentor fast-riser movies, this is a good one. Shades of Wall Street. Shades of Devil’s Advocate.”
  — Chris Ryan [12:00]

• “McConaughey is in a weird part of his career here...maybe his biggest problem is he’s a likable presence…but he’s not a great actor. He always plays himself.”
  — Bill Simmons [18:46]

• “[Pacino] can still turn the fastball.”
  — Chris Ryan [24:02]

• “You're selling certainty in an uncertain world.”
  — Pacino as Walter Abrams [25:12]

• “Modesty’s not a virtue. It might be a vice.”
  — Pacino [25:04]

• “It’s luck. Might as well flip a coin. Oh, he did flip a coin. Look at that.”
  — Sal [103:04]

Timestamps for Key Segments

• 00:53-01:30 — The film’s odd release timing (Columbus Day), critique of marketing choices
• 03:22-04:45 — Background on the explosion of sports betting content and movies in the early 2000s
• 06:30-10:05 — Recollections of ’90s touts, sports betting culture, and scams
• 12:00-14:45 — Archetypes of mentor/mentee movies and this one’s twist
• 17:08-21:04 — McConaughey’s career context, charm, and pre-McConaissance struggles
• 23:51-29:11 — Pacino’s legacy, performance, and rewatchable lines
• 34:34-48:00 — Breakdown of most rewatchable scenes: QB montage, lemons speech, TV parodies
• 49:50-54:00 — Most 2005 details: fax machines, illegal gambling, tout shows
• 63:13-66:31 — What’s aged the worst; head-scratching over the film title’s meaning
• 70:17-70:55 — Bill’s perennial wish: a movie where the hero just keeps winning
• 79:15-81:34 — Old-school analog fantasy sports, chasing box scores
• 97:00-97:35 — Legendary tale: Sal’s friend joins the Navy to escape a gambling debt

Segmented Highlights

[13:14] — “Slicking back your hair as a movie identity change”

A classic trope invoked for a character’s transformation, humorously discussed.

[29:26] — “When did Pacino go full raspy voice?”

Exploring Pacino’s evolution and his enduring status as the ‘gift goat’ of meme-able acting moments.

[47:25] — “The Lemons Speech”

Pacino dismantles the Gamblers Anonymous meeting with biting, existential monologue—instantly rewatchable.

[66:13] — “What does Two for the Money even mean?”

The show’s running confusion over the nonsensical title. Suggested alternates: “Money Line,” “Laying Wood,” “Chasing the Vague Hot Streak.”

[71:45] — “Dion Waiters Award”

Nominees for most memorable minor character include Piven’s Ari-like Jerry Sykes and Chuck Adler’s over-the-top cameo.

[95:48] — “Sal’s friend joins the Navy to dodge a gambling debt”

A legendary real-life tale of loss and escape, emblematic of the era.

Final Thoughts & Verdict

Two for the Money stands as a time capsule of a vanished world—before legal betting, before smartphones, when touts promised locks and “systems” on late-night TV. The film’s campy energy, memorable performances (especially Pacino’s), and windows into male sports obsessions make it a uniquely rewatchable oddity, even if modern viewers see it as dated or nonsensical. The Rewatchables crew embrace both its flaws and its charms, making the case that, for nostalgia, background viewing, and Pacino completists, Two for the Money is a long-odds bet worth revisiting.

Who Won the Movie?

• Chris Ryan: “Pacino—he takes it from fine to rewatchable.”
• Sal: “McConaughey—this pivoted his whole arc.”
• Consensus: Pacino’s scenery-chewing performance, but McConaughey also gets his due as the eventual comeback kid.

For Further Watching

• Double Feature Suggestions: Rounders, Devil’s Advocate
• Sports Gambling Classics: The Gambler, Uncut Gems

“I just want one TV show or movie where the guy just wins the whole time and then the movie ends…Let me go for the ride with you. My God, you went 29 and 2. That was amazing. End credits. Now I’m rich.”
— Bill Simmons [70:17]

This summary captures the best of The Rewatchables’ deep cut into a forgotten genre flick, blending sports history, pop culture, and tongue-in-cheek commentary—perfect for newcomers and super-fans alike.