Home/Episodes/Two for the Money
‘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 · ▶ Listen on Spotify
Categories
What's Aged the Best
Bill SimmonsThe sports gambling touting culture - the movie captures exactly what the 1990s sports advisors phenomenon was like▶ 6:15
Chris RyanThe sports gambling touting culture - specifically mentions it's both what's aged the best and worst▶ 5:11
Most Rewatchable Scene
Bill SimmonsMcConaughey 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▶ 30:52
Chris RyanEngaged in discussion about the football scenes and Pacino's rehab speech but didn't clearly state specific picks▶ 32:14
Cousin SalDiscussed the Brandon shirtless/working out scene and engaged with the TV show psych system scene but didn't clearly state independent picks▶ 33:45
Overacting Award
Bill SimmonsMatthew McConaughey — Matthew McConaughey for his sports advisor scene where he delivers the 'every QB knows the secret' speech and 'makes love to the camera'▶ 37:44
Chris RyanMatthew 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▶ 38:10
Cousin SalMatthew McConaughey — Supports the McConaughey pick, focusing on how he broke from the script and went off-script during the sports advisor scene▶ 38:55
Butch's Girlfriend Award
Bill SimmonsThe ending with winning the big game and the Renee Russo marriage subplot interspersed with the game▶ 1:02:23
Chris RyanThe Armand Asante character/Novian storyline that gets introduced as a threat then abandoned▶ 59:58
Cousin SalMultiple issues including the seven-year-old daughter character and Jeremy Piven's underutilized character▶ 1:00:54
Stephen A. Smith Hottest Take Award
Bill SimmonsWants one TV show or movie where the guy just wins the whole time and the movie ends - no fall from grace arc▶ 1:09:53
Chris RyanThey should remake this movie as a period piece, setting it in the Wild West of sports gambling before it became legal▶ 1:07:04
Casting What-Ifs
Bill SimmonsDan Futterman — Not much to discuss - Russo's husband wrote the movie for her, and Dan Futterman was considered for Pacino's role▶ 1:10:51
Chris RyanEdward Norton — Edward Norton as Brandon in a darker Paul Verhoeven-directed version with Michael Douglas▶ 1:12:46
Apex Mountain
Bill SimmonsJeremy 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▶ 1:19:16
Chris RyanJohnny Utah — Discussed fictional football players derailed by injury - mentioned Jason Street and Johnny Utah as contenders▶ 1:25:01
Cousin SalJeremy 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▶ 1:23:55
Probably Unanswerable Questions
Bill SimmonsIs Pacino the number one draft pick for the movie Cook draft for guys you'd want to play the Cook?▶ 1:38:18
Chris RyanIs Monday Night Football's popularity really based on the gambling losses of betters from the weekend?▶ 1:35:14
Coach Finstock Life Lesson
Bill SimmonsMultiple 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'▶ 1:41:48
Who Won the Movie
Cousin SalMatthew McConaughey — Initially said McConaughey because it pivoted his arc, but later agreed Pacino makes the movie entertaining and rewatchable▶ 1:42:17
Movies Referenced (34)
| Title (year) | Links | Mentions | Mentioned by | First |
|---|---|---|---|---|
| Dallas Buyers Club (2013) | IMDb ↗Lb ↗ | 3 | Chris Ryan, Bill Simmons | ▶ 17:48 |
| Donnie Brasco (1997) | IMDb ↗Lb ↗ | 3 | Cousin Sal, Chris Ryan | ▶ 12:28 |
| Back to the Future (1985) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 1:17 |
| Blood Diamond (2006) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 1:45:01 |
| Fargo (1996) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 1:14:35 |
| Friday Night Lights (2004) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 3:31 |
| Magic Mike (2012) | IMDb ↗Lb ↗ | 2 | Chris Ryan | ▶ 18:34 |
| Pearl Harbor (2001) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 1:19:14 |
| Philadelphia (1993) | IMDb ↗Lb ↗ | 2 | Chris Ryan | ▶ 6:33 |
| Scent of a Woman (1992) | IMDb ↗Lb ↗ | 2 | Bill Simmons, Chris Ryan | ▶ 23:48 |
| The Intern (2015) | IMDb ↗Lb ↗ | 2 | Cousin Sal, Chris Ryan | ▶ 1:08:50 |
| Wall Street (1987) | IMDb ↗Lb ↗ | 2 | Bill Simmons, Chris Ryan | ▶ 12:09 |
Directors Referenced (3)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Ari Gold | IMDb ↗Lb ↗ | 9 | Bill Simmons, Cousin Sal, Chris Ryan | ▶ 7:51 | |
| Paul Verhoeven | IMDb ↗Lb ↗ | 3 | Chris Ryan, Bill Simmons | RoboCop | ▶ 51:03 |
| Sean Penn | IMDb ↗Lb ↗ | 1 | Chris Ryan | Mystic River, 21 Grams, Dead Man Walking | ▶ 59:27 |
Actors Referenced (58)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Al Pacino | IMDb ↗Lb ↗ | 66 | Bill Simmons, Cousin Sal, Chris Ryan | Dog Day Afternoon, The Godfather | ▶ 3:53 |
| Matthew McConaughey | IMDb ↗Lb ↗ | 56 | Bill Simmons, Chris Ryan, Cousin Sal | Interstellar, Dallas Buyers Club, Magic Mike | ▶ 3:53 |
| John Anthony | IMDb ↗Lb ↗ | 21 | Bill Simmons, Chris Ryan, Cousin Sal | Rachel Getting Married | ▶ 25:07 |
| Jeremy Piven | IMDb ↗Lb ↗ | 11 | Bill Simmons, Cousin Sal | ▶ 53:44 | |
| Jerry Jones | IMDb ↗Lb ↗ | 8 | Bill Simmons, Chris Ryan, Cousin Sal | ▶ 4:58 | |
| Ralph Garman | IMDb ↗Lb ↗ | 7 | Bill Simmons, Cousin Sal, Chris Ryan | Ted, Ted 2, A Million Ways to Die in the West | ▶ 1:11:33 |
| Kevin Chapman | IMDb ↗Lb ↗ | 4 | Bill Simmons, Cousin Sal | CODA, Mystic River | ▶ 55:59 |
| Michael Douglas | IMDb ↗Lb ↗ | 4 | Chris Ryan, Bill Simmons | Wall Street, Romancing the Stone | ▶ 29:07 |
| Donald Trump | IMDb ↗Lb ↗ | 3 | Chris Ryan | Home Alone 2: Lost in New York | ▶ 50:17 |
| Jessica Simpson | IMDb ↗Lb ↗ | 3 | Chris Ryan, Cousin Sal | The Dukes of Hazzard, Employee of the Month | ▶ 52:11 |
| Kaiser Chiefs | IMDb ↗Lb ↗ | 3 | Cousin Sal | ▶ 8:17 | |
| Robert De Niro | IMDb ↗Lb ↗ | 3 | Bill Simmons, Chris Ryan, Cousin Sal | Cape Fear, Raging Bull, Taxi Driver | ▶ 22:59 |
Writers Referenced (8)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Jason Street | IMDb ↗Lb ↗ | 8 | Chris Ryan, Bill Simmons | ▶ 12:09 | |
| Johnny Cash | IMDb ↗Lb ↗ | 3 | Bill Simmons, Cousin Sal | Walk the Line | ▶ 7:51 |
| Dan Gilroy | IMDb ↗Lb ↗ | 2 | Chris Ryan | Nightcrawler | ▶ 46:15 |
| Alfred Hayes | IMDb ↗Lb ↗ | 1 | Cousin Sal | ▶ 1:20:08 | |
| Brian Koppelman | IMDb ↗Lb ↗ | 1 | Bill Simmons | Runaway Jury, Michael Clayton | ▶ 3:26 |
| Taylor Worst | IMDb ↗Lb ↗ | 1 | Bill Simmons | ▶ 1:17:06 | |
| Tony Gilroy | IMDb ↗Lb ↗ | 1 | Chris Ryan | Michael Clayton, Rogue One: A Star Wars Story | ▶ 46:15 |
| Vince Gilligan | IMDb ↗Lb ↗ | 1 | Cousin Sal | El Camino | ▶ 33:37 |
Cinematographers Referenced (2)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Bet Rourich | IMDb ↗Lb ↗ | 1 | Bill Simmons | ▶ 1:18:46 | |
| Michael Grantland | IMDb ↗Lb ↗ | 1 | Chris Ryan | The Other Guys | ▶ 18:29 |