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‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan

February 6, 2020 · Once Upon a Time... in Hollywood (2019) · Comedy · Drama · 1:22:29

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Most Rewatchable Scene

Bill Simmons▶ 31:11Multiple scenes including Sharon Tate watching her own movie at the theater, Cliff picking up the hitchhiker, Rick's freak out/breakdown scene, and Cliff going to the Spahn Ranch
Chris Ryan▶ 30:31Any scene of driving in this movie - every scene where people are just driving around listening to the radio
Sean Fennessey▶ 33:23Rick practicing his lines at his house by the pool and Rick's freak out scene (which he says will win the category)

What's Aged the Best

Bill Simmons▶ 40:39Rick Dalton's house, the dog Brandy, how they recreated 1969 Hollywood, production design and costumes, the Playboy Mansion, Bounty Law, 1960s airplanes, El Coyote restaurant, Rick's Italian movies, Fat Leo, and the extended cast
Chris Ryan▶ 45:25The accumulated works of Rick Dalton - all the Bounty Law stuff, the FBI episode, the Italian spaghetti westerns, Operation Dynamite
Sean Fennessey▶ 44:51The purposeful storytelling choices like the painting of Rick in his driveway (inspired by Lee Van Cleef's house), and Rick Dalton as an ode to actors like Macarrus and Chakarrus who could have been Steve McQueen but didn't get the chance

What's Aged the Worst

Bill Simmons▶ 50:44Damien Lewis as Steve McQueen - feels miscast due to baggage from his roles in Billions and Homeland, and the ogling Sharon Tate scene doesn't work
Chris Ryan▶ 51:09Agrees Damien Lewis is not good and miscast, also criticizes how the character is written as 'Mr. Exposition'
Sean Fennessey▶ 51:13Agrees Damien Lewis is miscast as Steve McQueen and it's one of the only things in the movie he doesn't like

Casting What-Ifs

Bill Simmons▶ 52:34Burt Reynolds — Discusses multiple casting what-ifs including Burt Reynolds for Bruce Dern's role, Jennifer Lawrence originally approached for Sharon Tate, Al Pacino role written specifically for him, and mentions having a choice for who should have played Dern's character but doesn't reveal it
Chris Ryan▶ 52:58Bruce Dern — Fine with Bruce Dern over Burt Reynolds, discusses Tim Roth and James Marsden being cut, mentions rumors about Samuel L. Jackson and Tom Cruise possibly being considered for roles
Sean Fennessey▶ 53:01Bruce Dern — Prefers Bruce Dern over Burt Reynolds because Reynolds would have been too much like Rick Dalton, while Dern was always the bad guy in Westerns

Joey Pants Award

Bill Simmons▶ 57:36Clifton Collins Jr. — Clifton Collins as the vaquero and Danielle Harris (little girl from Halloween 4, now a grown up Manson family lady)
Chris Ryan▶ 57:29James Remar — James Remar as Ugly Owl Hoot on Bounty Law (known from 48 Hours and The Warriors)
Sean Fennessey▶ 57:54Damon Herriman — Mentioned Rebecca Gayhart, Damon Harriman from Justified, and Clue Gallagher (bookstore owner who sells Tess of Ubervilles)

Probably Unanswerable Questions

Bill Simmons▶ 1:02:28What if they flipped the movie roles between the two leads?
Chris Ryan▶ 1:03:07Critiques the Jake Gyllenhaal/Gerard Butler suggestion, notes their physical differences and age gap, suggests Matt Damon and Ben Affleck as alternatives
Sean Fennessey▶ 1:02:40Discusses the role flip scenario and suggests Jake Gyllenhaal and Gerard Butler as alternative casting

Half-Assed Internet Research

Bill Simmons▶ 1:04:14Presents multiple trivia facts including Brad Pitt's ad-libbed line, Leo's genuine flamethrower reaction, Michael Madsen's Cadillac from Reservoir Dogs, Tarantino owning the Eros Theater, Mad Magazine prop details, and Leo owning The Maltese Falcon used in the film
Chris Ryan▶ 1:04:38Speculates the actor who gave Brad Pitt encouragement was Rappaport from True Romance, saying 'you're Brad fucking Pitt'
Sean Fennessey▶ 1:04:45Suggests Saul Rubinek as the actor who encouraged Brad Pitt, and notes Trudy character has some Jodie Foster inspiration due to her professional Western TV appearances

Apex Mountain

Bill Simmons▶ 1:08:14Ocean's Eleven — Ocean's Eleven for Brad Pitt (initially suggested Moneyball but changed after discussion about him dating Jennifer Aniston)
Chris Ryan▶ 1:07:59Ocean's Eleven — Ocean's Eleven for Brad Pitt (argued against Moneyball due to box office, brought up the Jennifer Aniston dating timeline)
Sean Fennessey▶ 1:07:52Moneyball — Moneyball for Brad Pitt

Best Quote

Bill Simmons▶ 1:12:50It could be one pool party away from starring in a Polanski movie
Bill Simmons▶ 1:12:59Hey, Dennis Hopper, move this fucking piece of shit
Sean Fennessey▶ 1:13:03Hey, you could do anything you want with him. Shit, throw him off a building, right? Light him on fire. Hit him with a Lincoln, right? Get creative. Do whatever you want. He's just happy for the opportunity

Who Won the Movie

Bill Simmons▶ 1:17:57Brad Pitt
Chris Ryan▶ 1:16:22Leonardo DiCaprio
Sean Fennessey▶ 1:17:38Quentin Tarantino

Movies Referenced (45)

Focus (2015)

9 mentions · Bill Simmons, Sean Fennessey▶ 32:41IMDb ↗Lb ↗

Moneyball (2011)

6 mentions · Bill Simmons, Sean Fennessey, Chris Ryan▶ 5:47IMDb ↗Lb ↗

Blood Diamond (2006)

4 mentions · Chris Ryan, Sean Fennessey▶ 5:08IMDb ↗Lb ↗

Boogie Nights (1997)

4 mentions · Bill Simmons, Chris Ryan, Sean Fennessey▶ 40:49IMDb ↗Lb ↗

Ocean's Eleven (2001)

4 mentions · Bill Simmons, Chris Ryan▶ 1:07:59IMDb ↗Lb ↗

The Revenant (2015)

4 mentions · Sean Fennessey, Bill Simmons▶ 9:04IMDb ↗Lb ↗

1917 (2019)

3 mentions · Bill Simmons, Sean Fennessey▶ 3:38IMDb ↗Lb ↗

Heat (1995)

3 mentions · Chris Ryan, Sean Fennessey▶ 20:19IMDb ↗Lb ↗

True Romance (1993)

3 mentions · Bill Simmons, Chris Ryan▶ 31:36IMDb ↗Lb ↗

Charlie's Angels (2000)

2 mentions · Bill Simmons▶ 11:44IMDb ↗Lb ↗

Elvis (2022)

2 mentions · Bill Simmons, Sean Fennessey▶ 1:00:49IMDb ↗Lb ↗

Fight Club (1999)

2 mentions · Bill Simmons▶ 5:55IMDb ↗Lb ↗

Directors Referenced (8)

Quentin Tarantino

35 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Reservoir Dogs, Pulp Fiction, From Dusk Till Dawn▶ 3:56IMDb ↗Lb ↗

Roman Polanski

5 mentions · Bill Simmons, Chris Ryan · Known for Chinatown▶ 46:21IMDb ↗Lb ↗

Baz Luhrmann

2 mentions · Sean Fennessey · Known for The Great Gatsby▶ 1:00:49IMDb ↗Lb ↗

John Cassavetes

2 mentions · Chris Ryan · Known for Rosemary's Baby▶ 1:14:58IMDb ↗Lb ↗

Clint Eastwood

1 mentions · Bill Simmons · Known for Million Dollar Baby, Gran Torino, Unforgiven▶ 17:00IMDb ↗Lb ↗

Hal Needham

1 mentions · Bill Simmons · Known for Smokey and the Bandit▶ 16:33IMDb ↗Lb ↗

Kevin Smith

1 mentions · Sean Fennessey · Known for Clerks, Chasing Amy▶ 48:06IMDb ↗Lb ↗

William Hoffa

1 mentions · Bill Simmons · Known for Limitless, Furious 7, Creed▶ 21:04IMDb ↗Lb ↗

Actors Referenced (69)

Brad Pitt

41 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Fight Club, 12 Monkeys, Mr. & Mrs. Smith▶ 4:46IMDb ↗Lb ↗

Rick Dalton

41 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for To Live and Die in L.A.▶ 1:47IMDb ↗Lb ↗

Bruce Lee

18 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Enter the Dragon▶ 25:32IMDb ↗Lb ↗

Sharon Tate

17 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Valley of the Dolls▶ 2:16IMDb ↗Lb ↗

Burt Reynolds

11 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Boogie Nights, Smokey and the Bandit, Striptease▶ 16:33IMDb ↗Lb ↗

Jude Law

10 mentions · Chris Ryan, Sean Fennessey, Bill Simmons · Known for The Talented Mr. Ripley, The Grand Budapest Hotel▶ 4:07IMDb ↗Lb ↗

Steve McQueen

10 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Great Escape▶ 16:13IMDb ↗Lb ↗

Al Pacino

9 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Dog Day Afternoon, The Godfather▶ 4:46IMDb ↗Lb ↗

Leonardo DiCaprio

8 mentions · Chris Ryan, Bill Simmons, Sean Fennessey · Known for Inception, The Wolf of Wall Street, The Departed▶ 4:57IMDb ↗Lb ↗

Bruce Dern

7 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Hateful Eight, Once Upon a Time... in Hollywood▶ 52:37IMDb ↗Lb ↗

James Marsden

7 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for X-Men, Enchanted▶ 53:20IMDb ↗Lb ↗

Neil Diamond

7 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Saving Silverman▶ 5:08IMDb ↗Lb ↗

Writers Referenced (3)

Jackie Files

2 mentions · Bill Simmons▶ 11:42IMDb ↗Lb ↗

Aaron Sorkin

1 mentions · Sean Fennessey · Known for A Few Good Men▶ 42:17IMDb ↗Lb ↗

Ed Burns

1 mentions · Sean Fennessey▶ 45:53IMDb ↗Lb ↗