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

November 25, 2025 · Two for the Money (2005) · Crime · Drama · Sport · 1:45:50

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What's Aged the Best

Bill Simmons▶ 6:15The sports gambling touting culture - the movie captures exactly what the 1990s sports advisors phenomenon was like
Chris Ryan▶ 5:11The sports gambling touting culture - specifically mentions it's both what's aged the best and worst

Most Rewatchable Scene

Bill Simmons▶ 30:52McConaughey playing quarterback in college with crazy long hair/hair extensions; Pacino's first scene with the hard sell to Brandon followed by Brandon figuring out his character and working on the tape; Pacino's gambling rehab speech about needing to feel alive; The TV show scene with the psych system explanation
Chris Ryan▶ 32:14Engaged in discussion about the football scenes and Pacino's rehab speech but didn't clearly state specific picks
Cousin Sal▶ 33:45Discussed the Brandon shirtless/working out scene and engaged with the TV show psych system scene but didn't clearly state independent picks

Overacting Award

Bill Simmons▶ 37:44Matthew McConaughey — Matthew McConaughey for his sports advisor scene where he delivers the 'every QB knows the secret' speech and 'makes love to the camera'
Chris Ryan▶ 38:10Matthew McConaughey — Agrees with McConaughey choice, discussing how he goes over the top as John Anthony then shifts to an intimate 'just you and me' delivery
Cousin Sal▶ 38:55Matthew McConaughey — Supports the McConaughey pick, focusing on how he broke from the script and went off-script during the sports advisor scene

Hall of Fame Plaque

Bill Simmons▶ 59:51First ballot smoker

Butch's Girlfriend Award

Bill Simmons▶ 1:02:23The ending with winning the big game and the Renee Russo marriage subplot interspersed with the game
Chris Ryan▶ 59:58The Armand Asante character/Novian storyline that gets introduced as a threat then abandoned
Cousin Sal▶ 1:00:54Multiple issues including the seven-year-old daughter character and Jeremy Piven's underutilized character

Stephen A. Smith Hottest Take Award

Bill Simmons▶ 1:09:53Wants one TV show or movie where the guy just wins the whole time and the movie ends - no fall from grace arc
Chris Ryan▶ 1:07:04They should remake this movie as a period piece, setting it in the Wild West of sports gambling before it became legal
Cousin Sal▶ 1:09:18James Baby Doll Dixon as Pacino for the remake

Casting What-Ifs

Bill Simmons▶ 1:10:51Dan Futterman — Not much to discuss - Russo's husband wrote the movie for her, and Dan Futterman was considered for Pacino's role
Chris Ryan▶ 1:12:46Edward Norton — Edward Norton as Brandon in a darker Paul Verhoeven-directed version with Michael Douglas
Cousin Sal▶ 1:13:38Tracy Morgan — Tracy Morgan doing McConaughey's character

Apex Mountain

Bill Simmons▶ 1:19:16Jeremy Piven — Jamie King - Pearl Harbor; Sports gambling movies - both The Gambler films; Piven - between this movie and Entourage seasons 1-2; Johnny Utah for fictional football players derailed by injury
Chris Ryan▶ 1:25:01Johnny Utah — Discussed fictional football players derailed by injury - mentioned Jason Street and Johnny Utah as contenders
Cousin Sal▶ 1:23:55Jeremy Piven — Noted Piven won Emmys for Ari Gold but has done hair restoration commercials recently; supported Jason Street as strong contender for fictional injured football players

Is This Movie Better With

Bill Simmons▶ 1:34:49James Gunn — James Gunn being involved and Buffalo Bill
Chris Ryan▶ 1:34:25Byron Mayo (notes that Walter is already doing Byron Mayo in the movie)
Cousin Sal▶ 1:34:36Mad Dog Russo screaming

Just One Oscar

Bill Simmons▶ 1:35:06Al Pacino — Pacino for Best Supporting Actor

Probably Unanswerable Questions

Bill Simmons▶ 1:38:18Is Pacino the number one draft pick for the movie Cook draft for guys you'd want to play the Cook?
Chris Ryan▶ 1:35:14Is Monday Night Football's popularity really based on the gambling losses of betters from the weekend?
Cousin Sal▶ 1:39:04How much did John Anthony earn?

Coach Finstock Life Lesson

Bill Simmons▶ 1:41:48Multiple options mentioned: 'Modesty is not a virtue. It might be a vice', 'Hot streaks go cold. Cold streaks go hot', and 'the Gambling Anonymous lemon speech'

Who Won the Movie

Bill Simmons▶ 1:42:13Al Pacino — Pacino
Chris Ryan▶ 1:42:15Matthew McConaughey — McConaughey
Cousin Sal▶ 1:42:17Matthew McConaughey — Initially said McConaughey because it pivoted his arc, but later agreed Pacino makes the movie entertaining and rewatchable

Movies Referenced (44)

Heat (1995)

4 mentions · Bill Simmons, Cousin Sal▶ 23:46IMDb ↗Lb ↗

Dallas Buyers Club (2013)

3 mentions · Chris Ryan, Bill Simmons▶ 17:48IMDb ↗Lb ↗

Donnie Brasco (1997)

3 mentions · Cousin Sal, Chris Ryan▶ 12:28IMDb ↗Lb ↗

Reality Bites (1994)

3 mentions · Bill Simmons, Chris Ryan▶ 10:13IMDb ↗Lb ↗

Back to the Future (1985)

2 mentions · Bill Simmons▶ 1:17IMDb ↗Lb ↗

Blood Diamond (2006)

2 mentions · Bill Simmons▶ 1:45:01IMDb ↗Lb ↗

Fargo (1996)

2 mentions · Bill Simmons▶ 1:14:35IMDb ↗Lb ↗

Friday Night Lights (2004)

2 mentions · Bill Simmons▶ 3:31IMDb ↗Lb ↗

Magic Mike (2012)

2 mentions · Chris Ryan▶ 18:34IMDb ↗Lb ↗

Pearl Harbor (2001)

2 mentions · Bill Simmons▶ 1:19:14IMDb ↗Lb ↗

Scent of a Woman (1992)

2 mentions · Bill Simmons, Chris Ryan▶ 23:48IMDb ↗Lb ↗

The Intern (2015)

2 mentions · Cousin Sal, Chris Ryan▶ 1:08:50IMDb ↗Lb ↗

Directors Referenced (3)

Ari Gold

9 mentions · Bill Simmons, Cousin Sal, Chris Ryan▶ 7:51IMDb ↗Lb ↗

Paul Verhoeven

3 mentions · Chris Ryan, Bill Simmons · Known for RoboCop▶ 51:03IMDb ↗Lb ↗

Sean Penn

1 mentions · Chris Ryan · Known for Mystic River, 21 Grams, Dead Man Walking▶ 59:27IMDb ↗Lb ↗

Actors Referenced (58)

Al Pacino

66 mentions · Bill Simmons, Cousin Sal, Chris Ryan · Known for Dog Day Afternoon, The Godfather▶ 3:53IMDb ↗Lb ↗

Matthew McConaughey

56 mentions · Bill Simmons, Chris Ryan, Cousin Sal · Known for Interstellar, Dallas Buyers Club, Magic Mike▶ 3:53IMDb ↗Lb ↗

John Anthony

21 mentions · Bill Simmons, Chris Ryan, Cousin Sal · Known for Rachel Getting Married▶ 25:07IMDb ↗Lb ↗

Jeremy Piven

11 mentions · Bill Simmons, Cousin Sal▶ 53:44IMDb ↗Lb ↗

Jerry Jones

8 mentions · Bill Simmons, Chris Ryan, Cousin Sal · Known for The Long Goodbye▶ 4:58IMDb ↗Lb ↗

Ralph Garman

7 mentions · Bill Simmons, Cousin Sal, Chris Ryan · Known for Ted, Ted 2, A Million Ways to Die in the West▶ 1:11:33IMDb ↗Lb ↗

Kevin Chapman

4 mentions · Bill Simmons, Cousin Sal · Known for CODA, Mystic River▶ 55:59IMDb ↗Lb ↗

Michael Douglas

4 mentions · Chris Ryan, Bill Simmons · Known for Wall Street, Romancing the Stone▶ 29:07IMDb ↗Lb ↗

Donald Trump

3 mentions · Chris Ryan · Known for Home Alone 2: Lost in New York▶ 50:17IMDb ↗Lb ↗

Jessica Simpson

3 mentions · Chris Ryan, Cousin Sal · Known for The Dukes of Hazzard, The Love Guru, Employee of the Month▶ 52:11IMDb ↗Lb ↗

Kaiser Chiefs

3 mentions · Cousin Sal▶ 8:17IMDb ↗Lb ↗

Robert De Niro

3 mentions · Bill Simmons, Chris Ryan, Cousin Sal · Known for Cape Fear, Raging Bull, Taxi Driver▶ 22:59IMDb ↗Lb ↗

Writers Referenced (8)

Jason Street

8 mentions · Chris Ryan, Bill Simmons▶ 12:09IMDb ↗Lb ↗

Johnny Cash

3 mentions · Bill Simmons, Cousin Sal · Known for Walk the Line▶ 7:51IMDb ↗Lb ↗

Dan Gilroy

2 mentions · Chris Ryan · Known for Nightcrawler▶ 46:15IMDb ↗Lb ↗

Alfred Hayes

1 mentions · Cousin Sal▶ 1:20:08IMDb ↗Lb ↗

Brian Koppelman

1 mentions · Bill Simmons · Known for Runaway Jury, Runner Runner, Michael Clayton▶ 3:26IMDb ↗Lb ↗

Taylor Worst

1 mentions · Bill Simmons▶ 1:17:06IMDb ↗Lb ↗

Tony Gilroy

1 mentions · Chris Ryan · Known for Michael Clayton, Rogue One: A Star Wars Story▶ 46:15IMDb ↗Lb ↗

Vince Gilligan

1 mentions · Cousin Sal · Known for El Camino▶ 33:37IMDb ↗Lb ↗

Cinematographers Referenced (2)

Bet Rourich

1 mentions · Bill Simmons▶ 1:18:46IMDb ↗Lb ↗

Michael Grantland

1 mentions · Chris Ryan · Known for The Other Guys▶ 18:29IMDb ↗Lb ↗