'Two for the Money'
Uh-oh, The Ringer's Bill Simmons, Chris Ryan, and Cousin Sal are gambling again! The guys fire up their favorite Monday night parlay after revisiting the 2005 sports thriller 'Two for the Money,' starring Matthew McConaughey, Al Pacino, and Rene Russo.

Cast
Matthew McConaughey as Brandon Lang / John Anthony
Al Pacino as Walter Abrams
Rene Russo as Toni Moran
Jeremy Piven as Jerry Sykes
Armand Assante as Novian
Notes
- Part of gambling month on the Rewatchables.
- Budget of $35 million, grossed $30.5 million. Released Columbus Day weekend – terrible timing.
- Director: D.J. Caruso (also did Eagle Eye). Writer: Dan Gilroy (Tony Gilroy's brother; met the real person at a golf course).
- Based loosely on a true story (real person: Brandon Link). Rene Russo's husband Dan Gilroy wrote the screenplay and wrote it for Russo.
- Pacino's 14th Rewatchable – #2 all-time behind Tom Cruise.
- McConaughey was in his 'fallow period' (2003-2008) before the McConaissance.
- Paul Tagliabue banned the movie's commercials from NFL games the first week.
- Bill wrote about this movie for Page 2 in 2005, forgot he wrote it. Described McConaughey as 'the Jimmy Jackson of Hollywood.'
- Craig (producer, first-time viewer): 'Upon first watch, I was like, you know, and then going back I'm like I'm starting to like this movie a little bit more.'
Categories
Quote from Rog's review:
“You could see Al Pacino doing something he's done a lot lately, having a terrific time being an actor.”
Ebert gave it 3.5 stars. Said McConaughey and Russo are wonderful too. The general public didn't agree – the movie lost money theatrically.
- Bill: Initially Pacino's 'I'm gambling again' speech/gambling rehab scene. Then switched to John Anthony's first Sports Advisors broadcast and the moment he goes off script – 'the energy in that scene is incredible.'
- CR: Same – the sports advisor broadcast. 'If you are walking by a television and Brandon Lang is getting the 'Pretty Woman' montage to turn into John Anthony, all right, I got to stick around.'
- Sal: Infiltrating Gamblers Anonymous – 'you're all lemons.' Also: the Armand Assante dinner scene.
- Sal: Nobu, fax machines, the allusion to 'this whole .com thing.'
- CR: Desert Storm-era jokes ('it's a scud attack this weekend'); a casual 'this guy would never be president' Donald Trump joke about his hair; sports betting still being illegal.
- Bill: Pacino saying 'I'm going to do this whole .com thing around him' – 'that's the last time anyone said .com.'
- Craig: Needing four TVs to watch four games – 'the OG quad box.' Also: giant telemarketer headsets the size of specialized football helmets.
- Bill: Pacino's character being based on Stu Finer, who's still on Barstool – 'just going to age great every year for the rest of my life.' Also: the struggling hairline Super Bowl between Pacino, McConaughey, and Piven.
- CR: Bringing a character into New York City for the first time. Pacino's line 'you shut your fucking toilet when I'm talking to her' – 'I've never heard somebody describe another person's mouth as a toilet.' Also: Winged Foot is still really hard to play.
- Sal: McConaughey's pecs. Piven's pettiness. Pacino's pep talks.
- Bill: This era of sports gambling is gone – 'from 7 centuries ago compared to where we are in 2025.' The 900 lines, unregulated bookies, over-the-top advisor shows.
- CR: Guys having heart attacks at work and taking pills – 'before the pill even reaches your stomach, it appears to have worked.'
- Bill: The title 'Two for the Money' – nobody knows what it means.
- CR: Armand Assante's Novian character introduced as a huge threat then abandoned.
Bill: Preemptively gives it to Pacino, who gets the overacting award across the board. 'That guy.'
- Bill: The ending – winning the big game/saving the business intercut with Russo trying to save her marriage. 'I just care about the game.'
- CR: Armand Assante's character – introduced as important, then abandoned with no resolution.
- Sal: Piven's character is underdeveloped; the 7-year-old daughter subplot.
- CR: Should remake this as a period piece about the Wild West of pre-legalization sports gambling.
- Sal's gambling stories: His friend Harry paid $400 for an 'ACC game of the year' pick (Duke +17, Florida State won 59-20). Sal himself went 18-0-2 giving picks on SportsCenter and nobody at ESPN cared.
- Bill: Kevin Chapman (from Mystic River and Person of Interest) – 'one of the great that guys.' Also: Brandon Lang's dad in the beginning was one of the bad guys in 'Road House'.
- CR: Ralph Garman as the producer of the TV show.
- Bill: Movies that play 'You're Nobody Till Somebody Loves You' by Dean Martin. Also: movies with Pacino as a cuck – 'this is my favorite for Apex Mountain.'
- Sal: Brandon Lang for fictional football players brought down by injuries.
- All three stars: Not their apex mountains.
Not formally discussed, but Bill mentioned it would work for Scorsese's energy.
Bill: Probably the Piven role or possibly Walter Abrams himself.
The Monday Night Football theme. Also: 'You're Nobody Till Somebody Loves You' by Dean Martin during the montage.
- Sal: Jeremy Piven's hair – 'I'd wear it every Sunday night on Guess the Lines.'
- CR: The Algorithm Psych System – whatever McConaughey was looking at on his computer.
- Bill: Game-worn McConaughey Sun Devils jersey from the opening scene, 'maybe with the hair extensions.'
- Bill: 'Modesty's not a virtue, it might be a vice.' Also: 'great hot streaks go cold, cold streaks go hot.'
- CR: The life lesson is the Gamblers Anonymous speech – 'two for three every week.'
- CR: 'Rounders' – 'the voice over, the way it opens, it just feels of a piece.'
- Bill: Devil's Advocate – 'Walter is Satan' followed by 'Two for the Money'.
- CR and Sal: Pacino. Bill: McConaughey – 'it pivoted his arc to do serious movies.'
- Craig: 'The movie goes from fine to entertaining and rewatchable because of Pacino. If it was just another actor, I don't know if you'd revisit it.'
Craig: Initially lukewarm, but upon rewatching clips, started to appreciate it more. 'Half the things Pacino does in this movie are hilarious.' Credits Pacino as the reason the movie works as a rewatchable. 'Hebrew National, dad's penis – that's what keeps you coming back.'