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‘The Sting’ With Bill Simmons, Chris Ryan, and Sean Fennessey

September 30, 2025 · The Sting (1973) · Comedy · Crime · Drama · 1:56:35

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Stephen A. Smith Hottest Take Award

Bill Simmons▶ 42:30Jack Lemmon wins for Save the Tiger (implying this was controversial/undeserved)
Sean Fennessey▶ 42:47Pacino should have won for Serpico (over Jack Lemmon's Save the Tiger win)

Most Rewatchable Scene

Bill Simmons▶ 52:11The poker scene where Newman shows off card tricks and plays poker
Chris Ryan▶ 52:16The first time Gondorf and Hooker meet when Gondorf is hungover
Sean Fennessey▶ 49:07Discussed multiple scenes including the counterfeit money scene with Snyder, but didn't give one definitive pick

What's Aged the Best

Bill Simmons▶ 56:54Multiple 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
Chris Ryan▶ 56:13The 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)

Big Kahuna Burger Award

Bill Simmons▶ 1:10:04The fake gin

Den of Thieves Benihana Award

Chris Ryan▶ 1:11:19Carousel Whorehouse

Butch's Girlfriend Award

Bill Simmons▶ 1:13:02The 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
Chris Ryan▶ 1:12:19The 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
Sean Fennessey▶ 1:15:15The 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

Casting What-Ifs

Bill Simmons▶ 1:25:02Jack Kehoe — Jack Kehoe for Best That Guy, Lonegan's henchman (Charles Deercop) for Damn Waiters Award
Chris Ryan▶ 1:25:07Charles Dierkop — Suggested Charles Deercop (Lonegan's bodyguard) for Best That Guy
Sean Fennessey▶ 1:25:35Harold Gould — Suggested Harold Gould as Kid Twist for Best That Guy, Dana Elkar as FBI agent for Damn Waiters Award

Apex Mountain

Bill Simmons▶ 1:31:02Robert 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)
Chris Ryan▶ 1:31:49Robert 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
Sean Fennessey▶ 1:31:30Robert 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

Hanks or Cruise

Bill Simmons▶ 1:36:56Tom Cruise — Both - Cruise as Johnny Hooker and Hanks as Newman, set in late 90s
Sean Fennessey▶ 1:36:36Tom Cruise — Both - Cruise as Johnny Hooker and Hanks as Newman (described as 'Hanks is Gandalf, Tom Cruise is Frodo')

Is This Movie Better With

Bill Simmons▶ 1:44:24Agrees with Mad Dog pick and does his own Mad Dog impression, mentions saving Wayne Jacobs for something else
Chris Ryan▶ 1:44:01Mad Dog Russo in the horse race parlor commenting on the betting
Sean Fennessey▶ 1:44:39Byron Mayo would crush in this environment with the scams and wars

Just One Oscar

Bill Simmons▶ 1:45:15Marvin Hamlisch — Hamlish (initially suggested, then agreed with Ward)
Chris Ryan▶ 1:45:17Ward (for the screenplay)

Probably Unanswerable Questions

Bill Simmons▶ 1:45:43What 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
Chris Ryan▶ 1:45:46Noted that Doyle was putting in forest-like conditions with no roll to the greens, questioning what 1930s golf was like
Sean Fennessey▶ 1:46:04Agreed Doyle cheated at golf and had a short game that was off

Who Won the Movie

Bill Simmons▶ 1:48:13Paul Newman — Newman initially, but also mentions George Roy Hill case for having both this and Butch Cassidy
Sean Fennessey▶ 1:48:14Robert Redford — Redford, because he walks out smelling like gold in this movie

Movies Referenced (75)

The Purge (2013)

8 mentions · Bill Simmons, Sean Fennessey▶ 1:16:17IMDb ↗Lb ↗

Funny Farm (1988)

7 mentions · Sean Fennessey, Bill Simmons▶ 1:49:25IMDb ↗Lb ↗

The Exorcist (1973)

6 mentions · Sean Fennessey, Bill Simmons, Chris Ryan▶ 40:50IMDb ↗Lb ↗

All the President's Men (1976)

5 mentions · Bill Simmons▶ 10:37IMDb ↗Lb ↗

Focus (2015)

5 mentions · Bill Simmons▶ 13:00IMDb ↗Lb ↗

Black Sunday (1960)

3 mentions · Bill Simmons, Sean Fennessey▶ 35:51IMDb ↗Lb ↗

Catch Me If You Can (2002)

3 mentions · Bill Simmons▶ 13:00IMDb ↗Lb ↗

Jaws (1975)

3 mentions · Bill Simmons▶ 35:51IMDb ↗Lb ↗

The Firm (1993)

3 mentions · Bill Simmons, Chris Ryan▶ 59:25IMDb ↗Lb ↗

Three Days of the Condor (1975)

3 mentions · Bill Simmons, Chris Ryan▶ 26:23IMDb ↗Lb ↗

Top Gun (1986)

3 mentions · Bill Simmons, Chris Ryan▶ 6:54IMDb ↗Lb ↗

All Is Lost (2013)

2 mentions · Sean Fennessey▶ 1:51:30IMDb ↗Lb ↗

Directors Referenced (10)

George Roy Hill

19 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Sting, Butch Cassidy and the Sundance Kid, Slap Shot▶ 2:59IMDb ↗Lb ↗

Warren Beatty

6 mentions · Chris Ryan, Sean Fennessey, Bill Simmons · Known for Heaven Can Wait▶ 29:45IMDb ↗Lb ↗

George Cukor

1 mentions · Sean Fennessey · Known for Gaslight, The Philadelphia Story▶ 27:15IMDb ↗Lb ↗

Howard Hawks

1 mentions · Sean Fennessey · Known for Rio Bravo▶ 27:15IMDb ↗Lb ↗

Iyi Tubi

1 mentions · Bill Simmons · Known for Ex Machina, World War Z▶ 12:05IMDb ↗Lb ↗

John Ford

1 mentions · Sean Fennessey · Known for The Quiet Man▶ 27:10IMDb ↗Lb ↗

Kosta Jokic

1 mentions · Sean Fennessey▶ 42:54IMDb ↗Lb ↗

Tom Brady

1 mentions · Bill Simmons · Known for The Hot Chick▶ 9:15IMDb ↗Lb ↗

Wayne Jacobs

1 mentions · Sean Fennessey▶ 1:43:37IMDb ↗Lb ↗

Woody Allen

1 mentions · Sean Fennessey · Known for Annie Hall, Deconstructing Harry▶ 41:39IMDb ↗Lb ↗

Actors Referenced (86)

Robert Redford

84 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Natural, Ordinary People, Butch Cassidy and the Sundance Kid▶ 1:56IMDb ↗Lb ↗

Paul Newman

61 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Road to Perdition, The Verdict▶ 2:59IMDb ↗Lb ↗

Robert Shaw

27 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Jaws, A Man for All Seasons, The Sting▶ 5:40IMDb ↗Lb ↗

Tom Cruise

15 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Top Gun, Minority Report▶ 6:54IMDb ↗Lb ↗

Tom Hanks

12 mentions · Bill Simmons, Sean Fennessey · Known for Cast Away, Big, Forrest Gump▶ 4:25IMDb ↗Lb ↗

Butch Cassidy

11 mentions · Bill Simmons, Sean Fennessey · Known for Hollywood Homicide▶ 2:59IMDb ↗Lb ↗

Al Pacino

9 mentions · Sean Fennessey, Bill Simmons, Chris Ryan · Known for Dog Day Afternoon, The Godfather▶ 33:10IMDb ↗Lb ↗

Brad Pitt

9 mentions · Bill Simmons, Sean Fennessey · Known for Fight Club, 12 Monkeys, Mr. & Mrs. Smith▶ 1:15IMDb ↗Lb ↗

David Ward

9 mentions · Sean Fennessey, Chris Ryan, Bill Simmons▶ 27:24IMDb ↗Lb ↗

Eddie Murphy

8 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Harlem Nights, The Nutty Professor▶ 11:58IMDb ↗Lb ↗

Timothée Chalamet

8 mentions · Bill Simmons, Sean Fennessey · Known for Call Me by Your Name, Lady Bird▶ 7:31IMDb ↗Lb ↗

Jack Kehoe

6 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for The Sting, Midnight Run▶ 38:59IMDb ↗Lb ↗

Writers Referenced (6)

Don Schlitz

10 mentions · Sean Fennessey, Bill Simmons, Chris Ryan · Known for Notting Hill, It Could Happen to You, King Richard▶ 34:12IMDb ↗Lb ↗

Scott Joplin

3 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Curious Case of Benjamin Button, The Sting▶ 39:20IMDb ↗Lb ↗

William Goldman

3 mentions · Chris Ryan, Bill Simmons · Known for Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride▶ 26:36IMDb ↗Lb ↗

Andy Greenwald

2 mentions · Bill Simmons, Chris Ryan▶ 8:05IMDb ↗Lb ↗

Ken Kesey

1 mentions · Sean Fennessey · Known for One Flew Over the Cuckoo's Nest▶ 23:56IMDb ↗Lb ↗

Roger Ebert

1 mentions · Bill Simmons▶ 44:09IMDb ↗Lb ↗