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‘Sideways’ With Bill Simmons, Chris Ryan, and Sean Fennessey

January 10, 2023 · Sideways (2004) · Comedy · Drama · Romance · 1:49:00

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Most Rewatchable Scene

Bill Simmons▶ 36:24Multiple scenes including the hitching post day one meeting Maya, the split-screen wine tasting into meeting Stephanie, and the Los Olivos dinner scene with the drunk dial

Big Kahuna Burger Award

Bill Simmons▶ 42:27The wine drinking scenes with Miles and Maya on the porch, including the Pinot monologue and Maya's wine philosophy response
Chris Ryan▶ 50:24Agrees with the wine scenes, particularly praising the dual monologues between Miles and Maya
Sean Fennessey▶ 45:25Agrees with the wine scenes, calling it 'the one' and praising the 7-8 minute kitchen/porch sequence

Den of Thieves Benihana Award

Bill Simmons▶ 58:49Mentioned the winery with barrels, outdoor picnic site, and generally praised all the Santa Barbara wine country locations that make viewers want to visit
Sean Fennessey▶ 59:16The Frass Canyon/Fest Parker winery in Los Olivos

Butch's Girlfriend Award

Bill Simmons▶ 1:00:27The fake car accident, specifically putting the concrete brick on the gas pedal
Sean Fennessey▶ 1:01:48The car accident (agrees with another host's pick)

Is There a Better Title?

Bill Simmons▶ 1:04:55Likes the current title 'Sideways', suggests 'The Day After Yesterday' as alternative, jokes about avoiding 'Whiners'
Chris Ryan▶ 1:05:08Mentions original book title was 'Two Guys on Wine' and agrees 'Sideways' was definitely better than that
Sean Fennessey▶ 1:05:06Rejects 'The Day After Yesterday' saying it sounds like a nuclear apocalypse movie

Ron Burgundy Flute Award

Bill Simmons▶ 1:05:27When he gets to the mom's house - you could sneak one in after you've seen it already, just need to know that he stole the money

Best Quote

Bill Simmons▶ 1:05:35If anyone orders Merlot, I'm leaving. I'm not drinking any fucking Merlot.

Casting What-Ifs

Bill Simmons▶ 1:12:57Robert Downey Jr. — George Clooney and Robert Downey Jr. for Miles - likes Downey as a challenge casting choice
Chris Ryan▶ 1:12:30Robert Downey Jr. — Robert Downey Jr. for Miles - thinks it's doable and Downey could capture the addiction part, suggests his Zodiac journalist approach would work
Sean Fennessey▶ 1:12:34Robert Downey Jr. — Robert Downey Jr. for Miles - thinks it would probably be a better movie but notes Downey has too much energy for the depression aspect

Overacting Award

Bill Simmons▶ 1:15:24Thomas Haden Church — Thomas Haden Church - specifically his breakdown scene where he begs Miles for help saying 'I know I fucked up... You gotta help me Miles... If I lose Christine I am nothing'
Chris Ryan▶ 1:16:04Jessica Hecht — Jessica Hecht - noting she has won this award multiple times on the podcast

Dion Waiters Award

Bill Simmons▶ 1:16:45M.C. Gainey — MC Ganey as angry naked guy

Apex Mountain

Bill Simmons▶ 1:24:07Paul Giamatti — Giamatti: John Adams/mid-2010s; Thomas Hayden Church: Yes; Santa Ynez: Yes; Virginia Madsen: Yes; Sandra Oh: No, Grey's Anatomy; Sandra Oh/Alexander Payne marriage: Yes; Pinot Noir: Yes; Saab Turbo: Yes
Chris Ryan▶ 1:24:05Paul Giamatti — Giamatti: John Adams over Billions; Sandra Oh: Killing Eve first season as potential apex
Sean Fennessey▶ 1:24:29Thomas Haden Church — Thomas Hayden Church discussion but no clear yes/no position stated

Hall of Fame Plaque

Bill Simmons▶ 1:29:22Alexander Payne - this is his Hall of Fame plaque movie
Chris Ryan▶ 1:29:31Thinks it's Election but acknowledges it's pretty close between the two films
Sean Fennessey▶ 1:29:27Alexander Payne - agrees this is his Hall of Fame plaque movie, citing it as his biggest hit, Oscar win for screenplay, and cultural impact on wine

Racehorse Name Award

Chris Ryan▶ 1:29:46Cranking my Johnson / Johnson Crank
Sean Fennessey▶ 1:29:53Smooched Bone

Is This Movie Better With

Bill Simmons▶ 1:35:01Wayne Jenkins, Danny Trejo, Catherine Hahn, Steve Buscemi, Sam Jackson, JT Walsh
Bill Simmons▶ 1:36:05Sammo Kam-Bo Hung — Super Samo as the third person next to Giamatti
Chris Ryan▶ 1:35:15Wayne Jenkins as MC Ganey
Chris Ryan▶ 1:35:44Wayne Jenkins serving Miles at the Spittoon Winery
Sean Fennessey▶ 1:35:58Sammo Kam-Bo Hung — Super Samo

Just One Oscar

Bill Simmons▶ 1:36:30Paul Giamatti — Initially says Giamatti, then agrees with Payne
Sean Fennessey▶ 1:36:34Alexander Payne — Payne (and Taylor) for the script

Probably Unanswerable Questions

Bill Simmons▶ 1:36:40Why did Jack and Miles like each other? How bad was Miles as a sex partner after seven bottles of wine?
Chris Ryan▶ 1:37:04How do Miles and Jack even stay in touch? What does it say about the public school system that Miles teaches eighth-grade English?

Coach Finstock Life Lesson

Bill Simmons▶ 1:42:08If you're writing a novel, try not to make it 1000 pages / don't write a novel
Chris Ryan▶ 1:42:02If your first novel is really just only getting started at page 750, maybe don't
Sean Fennessey▶ 1:41:54Try to avoid alcoholism

Who Won the Movie

Bill Simmons▶ 1:43:20Alexander Payne — Alexander Payne - because this movie gave him lasting filmography appeal and made people buy 'season tickets' for his future films
Chris Ryan▶ 1:43:04Paul Giamatti — Paul Giamatti - prevented him from being just a supporting actor for life and made him a leading man
Sean Fennessey▶ 1:42:22Paul Giamatti — Paul Giamatti - because it made him a movie star and led to major roles like John Adams and Billions

Movies Referenced (52)

The Aviator (2004)

5 mentions · Bill Simmons▶ 27:37IMDb ↗Lb ↗

About Schmidt (2002)

4 mentions · Bill Simmons, Sean Fennessey▶ 7:18IMDb ↗Lb ↗

American Splendor (2003)

4 mentions · Sean Fennessey, Bill Simmons▶ 21:35IMDb ↗Lb ↗

Collateral (2004)

4 mentions · Bill Simmons, Chris Ryan▶ 28:34IMDb ↗Lb ↗

Finding Neverland (2004)

4 mentions · Bill Simmons, Sean Fennessey▶ 29:56IMDb ↗Lb ↗

Million Dollar Baby (2004)

4 mentions · Bill Simmons▶ 27:32IMDb ↗Lb ↗

The Descendants (2011)

3 mentions · Bill Simmons, Sean Fennessey▶ 23:33IMDb ↗Lb ↗

Vera Drake (2004)

3 mentions · Bill Simmons▶ 30:02IMDb ↗Lb ↗

Fargo (1996)

2 mentions · Bill Simmons▶ 26:55IMDb ↗Lb ↗

Groundhog Day (1993)

2 mentions · Bill Simmons▶ 4:25IMDb ↗Lb ↗

Michael Clayton (2007)

2 mentions · Bill Simmons▶ 1:09:58IMDb ↗Lb ↗

Private Parts (1997)

2 mentions · Bill Simmons▶ 1:17:31IMDb ↗Lb ↗

Directors Referenced (14)

Alexander Payne

33 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Descendants▶ 6:47IMDb ↗Lb ↗

Will Kistler

12 mentions · Bill Simmons, Sean Fennessey · Known for The Incredible Hulk, Ant-Man▶ 20:18IMDb ↗Lb ↗

Clint Eastwood

5 mentions · Bill Simmons, Sean Fennessey · Known for Million Dollar Baby, Gran Torino, Unforgiven▶ 27:37IMDb ↗Lb ↗

Hal Ashby

5 mentions · Sean Fennessey, Bill Simmons · Known for In the Heat of the Night, Harold and Maude, Being There▶ 6:53IMDb ↗Lb ↗

Michael Mann

4 mentions · Sean Fennessey, Bill Simmons, Chris Ryan · Known for The Insider, Collateral, The Last of the Mohicans▶ 34:25IMDb ↗Lb ↗

Kosta Jokic

3 mentions · Bill Simmons▶ 44:29IMDb ↗Lb ↗

Taylor Hackford

3 mentions · Chris Ryan, Bill Simmons · Known for Dolores Claiborne▶ 34:25IMDb ↗Lb ↗

Warren Beatty

3 mentions · Bill Simmons · Known for Heaven Can Wait▶ 54:13IMDb ↗Lb ↗

Martin Scorsese

2 mentions · Bill Simmons, Sean Fennessey · Known for Taxi Driver, Killers of the Flower Moon, Mean Streets▶ 27:37IMDb ↗Lb ↗

Paul Bellany

2 mentions · Sean Fennessey, Bill Simmons · Known for Stardust▶ 0:00IMDb ↗Lb ↗

Claiborne Lashley

1 mentions · Sean Fennessey▶ 1:39:22IMDb ↗Lb ↗

Jason Reitman

1 mentions · Bill Simmons · Known for Up in the Air, Saturday Night▶ 8:26IMDb ↗Lb ↗

Actors Referenced (75)

Jack Nicholson

57 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Chinatown, As Good as It Gets, The Departed▶ 6:27IMDb ↗Lb ↗

Paul Giamatti

36 mentions · Sean Fennessey, Bill Simmons, Chris Ryan · Known for Sideways, Cinderella Man, American Splendor▶ 10:19IMDb ↗Lb ↗

Felicien Pinot

24 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for The Beast▶ 16:46IMDb ↗Lb ↗

Krista Saab

13 mentions · Bill Simmons, Chris Ryan · Known for American Gangster▶ 1:00:30IMDb ↗Lb ↗

Makabe Ganey

11 mentions · Bill Simmons, Chris Ryan · Known for Justice League, The Founder▶ 52:05IMDb ↗Lb ↗

Daniel Sea

9 mentions · Bill Simmons, Sean Fennessey▶ 20:04IMDb ↗Lb ↗

Don Johnson

7 mentions · Bill Simmons, Chris Ryan · Known for Django Unchained▶ 1:46IMDb ↗Lb ↗

Mike Lee

6 mentions · Chris Ryan, Bill Simmons, Sean Fennessey▶ 5:20IMDb ↗Lb ↗

Virginia Madsen

6 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Sideways▶ 30:46IMDb ↗Lb ↗

Andy Richter

4 mentions · Bill Simmons, Sean Fennessey▶ 1:45:07IMDb ↗Lb ↗

Bill Murray

3 mentions · Chris Ryan, Sean Fennessey · Known for Lost in Translation, Rushmore, Moonrise Kingdom▶ 4:19IMDb ↗Lb ↗

Bob Cousy

3 mentions · Bill Simmons · Known for Celtic Pride, Blue Chips▶ 4:29IMDb ↗Lb ↗

Writers Referenced (4)

Rex Pickett

7 mentions · Bill Simmons, Chris Ryan · Known for Sideways▶ 22:18IMDb ↗Lb ↗

Brian Koppelman

1 mentions · Bill Simmons · Known for Runaway Jury, Runner Runner, Michael Clayton▶ 1:08:33IMDb ↗Lb ↗

Harvey Weinstein

1 mentions · Sean Fennessey · Known for Shakespeare in Love, The Hateful Eight▶ 31:36IMDb ↗Lb ↗

William Goldman

1 mentions · Bill Simmons · Known for Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride▶ 1:37:45IMDb ↗Lb ↗

Cinematographers Referenced (1)

Christophe Legal

2 mentions · Bill Simmons, Chris Ryan · Known for The Pink Panther▶ 1:29:04IMDb ↗Lb ↗