‘The Sting’ With Bill Simmons, Chris Ryan, and Sean Fennessey
September 30, 2025 · The Sting (1973) · Comedy · Crime · Drama · 1:56:35
Categories
Most Rewatchable Scene
Sean FennesseyDiscussed multiple scenes including the counterfeit money scene with Snyder, but didn't give one definitive pick▶ 49:07
What's Aged the Best
Bill SimmonsMultiple elements: the great clothes (three-piece suits and fedoras), how scams like fixing races/counterfeit money/cheating at poker seemed easier back then, pickpocketing as an underutilized movie device, train trips with stars, and various character details▶ 56:54
Chris RyanThe movie's inversion of everything - it's about the depression but everyone's dressed snazzy, it's an anxious situation but everyone's cool as shit, high stakes but cool characters (like Ocean's 11)▶ 56:13
Butch's Girlfriend Award
Bill SimmonsThe lack of a 1936 babe/attractive woman character in the movie - there should have been a romantic element or female character to ensnare someone in the con▶ 1:13:02
Chris RyanThe subplot of the two other hitmen Cole and Sullivan pursuing Hooker - it's unnecessary and confusing to have yet another team of hitmen chasing him▶ 1:12:19
Sean FennesseyThe pacing after the Blue Note scene - it takes too long to get to the big finale, with too much time spent on Ray Walston helping set up situations▶ 1:15:15
Casting What-Ifs
Bill SimmonsJack Kehoe — Jack Kehoe for Best That Guy, Lonegan's henchman (Charles Deercop) for Damn Waiters Award▶ 1:25:02
Chris RyanCharles Dierkop — Suggested Charles Deercop (Lonegan's bodyguard) for Best That Guy▶ 1:25:07
Sean FennesseyHarold Gould — Suggested Harold Gould as Kid Twist for Best That Guy, Dana Elkar as FBI agent for Damn Waiters Award▶ 1:25:35
Apex Mountain
Bill SimmonsRobert Redford — Yes for Redford (this specific moment where he could do whatever he wanted), Yes for George Roy Hill (wins Best Director), Yes for Marvin Hamlisch, Yes for con movies (most successful one), No for Newman (Cool Hand Luke in mid-60s was his peak)▶ 1:31:02
Chris RyanRobert Redford — Participated in discussion about Redford and Leonardo DiCaprio's first call status, noted Eileen Brennan just walks up and down hallway but has incredible presence▶ 1:31:49
Sean FennesseyRobert Redford — Yes for Redford (Way We Were and this movie same year, both top 10 biggest movies), discussed Leonardo DiCaprio's long-running first call status since Titanic▶ 1:31:30
Hanks or Cruise
Bill SimmonsTom Cruise — Both - Cruise as Johnny Hooker and Hanks as Newman, set in late 90s▶ 1:36:56
Sean FennesseyTom Cruise — Both - Cruise as Johnny Hooker and Hanks as Newman (described as 'Hanks is Gandalf, Tom Cruise is Frodo')▶ 1:36:36
Is This Movie Better With
Bill SimmonsAgrees with Mad Dog pick and does his own Mad Dog impression, mentions saving Wayne Jacobs for something else▶ 1:44:24
Probably Unanswerable Questions
Bill SimmonsWhat was Doyle's handicap? He thinks Doyle was about a 15 handicap, a big hitter who cheated a lot by kicking the ball out of the rough▶ 1:45:43
Chris RyanNoted that Doyle was putting in forest-like conditions with no roll to the greens, questioning what 1930s golf was like▶ 1:45:46
Who Won the Movie
Bill SimmonsPaul Newman — Newman initially, but also mentions George Roy Hill case for having both this and Butch Cassidy▶ 1:48:13
Sean FennesseyRobert Redford — Redford, because he walks out smelling like gold in this movie▶ 1:48:14
Movies Referenced (64)
| Title (year) | Links | Mentions | Mentioned by | First |
|---|---|---|---|---|
| The Purge (2013) | IMDb ↗Lb ↗ | 8 | Bill Simmons, Sean Fennessey | ▶ 1:16:17 |
| The Exorcist (1973) | IMDb ↗Lb ↗ | 6 | Sean Fennessey, Bill Simmons, Chris Ryan | ▶ 40:50 |
| All the President's Men (1976) | IMDb ↗Lb ↗ | 5 | Bill Simmons | ▶ 10:37 |
| Catch Me If You Can (2002) | IMDb ↗Lb ↗ | 3 | Bill Simmons | ▶ 13:00 |
| Jaws (1975) | IMDb ↗Lb ↗ | 3 | Bill Simmons | ▶ 35:51 |
| Step Up (2006) | IMDb ↗Lb ↗ | 3 | Bill Simmons, Chris Ryan | ▶ 1:56:05 |
| Three Days of the Condor (1975) | IMDb ↗Lb ↗ | 3 | Bill Simmons, Chris Ryan | ▶ 26:23 |
| Top Gun (1986) | IMDb ↗Lb ↗ | 3 | Bill Simmons, Chris Ryan | ▶ 6:54 |
| All Is Lost (2013) | IMDb ↗Lb ↗ | 2 | Sean Fennessey | ▶ 1:51:30 |
| Casablanca (1942) | IMDb ↗Lb ↗ | 2 | Sean Fennessey | ▶ 1:18:35 |
| Dirty Harry (1971) | IMDb ↗Lb ↗ | 2 | Bill Simmons, Sean Fennessey | ▶ 24:29 |
| Dogma (1999) | IMDb ↗Lb ↗ | 2 | Chris Ryan, Sean Fennessey | ▶ 3:36 |
Directors Referenced (11)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| George Roy Hill | IMDb ↗Lb ↗ | 19 | Bill Simmons, Sean Fennessey, Chris Ryan | The Sting, Butch Cassidy and the Sundance Kid, Slap Shot | ▶ 2:59 |
| Warren Beatty | IMDb ↗Lb ↗ | 6 | Chris Ryan, Sean Fennessey, Bill Simmons | Heaven Can Wait | ▶ 29:45 |
| George Cukor | IMDb ↗Lb ↗ | 1 | Sean Fennessey | Gaslight | ▶ 27:15 |
| Howard Hawks | IMDb ↗Lb ↗ | 1 | Sean Fennessey | ▶ 27:15 | |
| Iyi Tubi | IMDb ↗Lb ↗ | 1 | Bill Simmons | Ex Machina, World War Z | ▶ 12:05 |
| John Ford | IMDb ↗Lb ↗ | 1 | Sean Fennessey | ▶ 27:10 | |
| John Huston | IMDb ↗Lb ↗ | 1 | Sean Fennessey | The Treasure of the Sierra Madre, Chinatown | ▶ 24:22 |
| Kosta Jokic | IMDb ↗Lb ↗ | 1 | Sean Fennessey | ▶ 42:54 | |
| Tom Brady | IMDb ↗Lb ↗ | 1 | Bill Simmons | The Hot Chick | ▶ 9:15 |
| Wayne Jacobs | IMDb ↗Lb ↗ | 1 | Sean Fennessey | ▶ 1:43:37 | |
| Woody Allen | IMDb ↗Lb ↗ | 1 | Sean Fennessey | Annie Hall | ▶ 41:39 |
Actors Referenced (88)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Robert Redford | IMDb ↗Lb ↗ | 84 | Bill Simmons, Sean Fennessey, Chris Ryan | The Natural, Ordinary People, Butch Cassidy and the Sundance Kid | ▶ 1:56 |
| Paul Newman | IMDb ↗Lb ↗ | 61 | Bill Simmons, Sean Fennessey, Chris Ryan | Road to Perdition, The Verdict | ▶ 2:59 |
| Robert Shaw | IMDb ↗Lb ↗ | 27 | Bill Simmons, Chris Ryan, Sean Fennessey | Jaws, A Man for All Seasons, The Sting | ▶ 5:40 |
| Tom Cruise | IMDb ↗Lb ↗ | 15 | Bill Simmons, Sean Fennessey, Chris Ryan | Top Gun, Minority Report | ▶ 6:54 |
| Tom Hanks | IMDb ↗Lb ↗ | 12 | Bill Simmons, Sean Fennessey | Cast Away, Big, Forrest Gump | ▶ 4:25 |
| Butch Cassidy | IMDb ↗Lb ↗ | 11 | Bill Simmons, Sean Fennessey | ▶ 2:59 | |
| Al Pacino | IMDb ↗Lb ↗ | 9 | Sean Fennessey, Bill Simmons, Chris Ryan | Dog Day Afternoon, The Godfather | ▶ 33:10 |
| Brad Pitt | IMDb ↗Lb ↗ | 9 | Bill Simmons, Sean Fennessey | Fight Club, 12 Monkeys, Mr. & Mrs. Smith | ▶ 1:15 |
| David Ward | IMDb ↗Lb ↗ | 9 | Sean Fennessey, Chris Ryan, Bill Simmons | ▶ 27:24 | |
| Eddie Murphy | IMDb ↗Lb ↗ | 8 | Bill Simmons, Sean Fennessey, Chris Ryan | The Nutty Professor, Beverly Hills Cop II | ▶ 11:58 |
| Timothée Chalamet | IMDb ↗Lb ↗ | 8 | Bill Simmons, Sean Fennessey | Call Me by Your Name, Lady Bird | ▶ 7:31 |
| Jack Kehoe | IMDb ↗Lb ↗ | 6 | Bill Simmons, Chris Ryan, Sean Fennessey | The Sting, Midnight Run | ▶ 38:59 |
Writers Referenced (6)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Don Schlitz | IMDb ↗Lb ↗ | 10 | Sean Fennessey, Bill Simmons, Chris Ryan | Notting Hill, It Could Happen to You, King Richard | ▶ 34:12 |
| Scott Joplin | IMDb ↗Lb ↗ | 3 | Bill Simmons, Sean Fennessey, Chris Ryan | The Curious Case of Benjamin Button, The Sting | ▶ 39:20 |
| William Goldman | IMDb ↗Lb ↗ | 3 | Chris Ryan, Bill Simmons | Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride | ▶ 26:36 |
| Andy Greenwald | IMDb ↗Lb ↗ | 2 | Bill Simmons, Chris Ryan | ▶ 8:05 | |
| Ken Kesey | IMDb ↗Lb ↗ | 1 | Sean Fennessey | One Flew Over the Cuckoo's Nest | ▶ 23:56 |
| Roger Ebert | IMDb ↗Lb ↗ | 1 | Bill Simmons | ▶ 44:09 |