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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 SimmonsMultiple 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▶ 36:24

Big Kahuna Burger Award

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

Den of Thieves Benihana Award

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

Butch's Girlfriend Award

Bill SimmonsThe fake car accident, specifically putting the concrete brick on the gas pedal▶ 1:00:27
Sean FennesseyThe car accident (agrees with SPEAKER_00's pick)▶ 1:01:48

Is There a Better Title?

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

Ron Burgundy Flute Award

Bill SimmonsWhen 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▶ 1:05:27

Best Quote

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

Casting What-Ifs

Bill SimmonsRobert Downey Jr.George Clooney and Robert Downey Jr. for Miles - likes Downey as a challenge casting choice▶ 1:12:57
Chris RyanRobert 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▶ 1:12:30
Sean FennesseyRobert 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▶ 1:12:34

Overacting Award

Bill SimmonsThomas Haden ChurchThomas 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'▶ 1:15:24
Chris RyanJessica HechtJessica Hecht - noting she has won this award multiple times on the podcast▶ 1:16:04

Dion Waiters Award

Bill SimmonsM.C. GaineyMC Ganey as angry naked guy▶ 1:16:45

Apex Mountain

Bill SimmonsPaul GiamattiGiamatti: 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▶ 1:24:07
Chris RyanPaul GiamattiGiamatti: John Adams over Billions; Sandra Oh: Killing Eve first season as potential apex▶ 1:24:05
Sean FennesseyThomas Haden ChurchThomas Hayden Church discussion but no clear yes/no position stated▶ 1:24:29

Hall of Fame Plaque

Bill SimmonsAlexander Payne - this is his Hall of Fame plaque movie▶ 1:29:22
Chris RyanThinks it's Election but acknowledges it's pretty close between the two films▶ 1:29:31
Sean FennesseyAlexander 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▶ 1:29:27

Racehorse Name Award

Chris RyanCranking my Johnson / Johnson Crank▶ 1:29:46
Sean FennesseySmooched Bone▶ 1:29:53

Is This Movie Better With

Bill SimmonsWayne Jenkins, Danny Trejo, Catherine Hahn, Steve Buscemi, Sam Jackson, JT Walsh▶ 1:35:01
Bill SimmonsSammo Kam-Bo HungSuper Samo as the third person next to Giamatti▶ 1:36:05
Chris RyanWayne Jenkins as MC Ganey▶ 1:35:15
Chris RyanWayne Jenkins serving Miles at the Spittoon Winery▶ 1:35:44
Sean FennesseySammo Kam-Bo HungSuper Samo▶ 1:35:58

Just One Oscar

Bill SimmonsPaul GiamattiInitially says Giamatti, then agrees with Payne▶ 1:36:30
Sean FennesseyAlexander PaynePayne (and Taylor) for the script▶ 1:36:34

Probably Unanswerable Questions

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

Coach Finstock Life Lesson

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

Who Won the Movie

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

Movies Referenced (52)

Title (year)LinksMentionsMentioned byFirst
Crank (2006)IMDb ↗Lb ↗7Bill Simmons, Chris Ryan▶ 52:02
The Aviator (2004)IMDb ↗Lb ↗5Bill Simmons▶ 27:37
The Beach (2000)IMDb ↗Lb ↗5Bill Simmons, Sean Fennessey▶ 12:11
About Schmidt (2002)IMDb ↗Lb ↗4Bill Simmons, Sean Fennessey▶ 7:18
Finding Neverland (2004)IMDb ↗Lb ↗4Bill Simmons, Sean Fennessey▶ 29:56
Million Dollar Baby (2004)IMDb ↗Lb ↗4Bill Simmons▶ 27:32
The Descendants (2011)IMDb ↗Lb ↗3Bill Simmons, Sean Fennessey▶ 23:33
Before Sunset (2004)IMDb ↗Lb ↗2Bill Simmons, Sean Fennessey▶ 28:39
Casino (1995)IMDb ↗Lb ↗2Bill Simmons▶ 1:34:06
Fargo (1996)IMDb ↗Lb ↗2Bill Simmons▶ 26:55
Groundhog Day (1993)IMDb ↗Lb ↗2Bill Simmons▶ 4:25
Michael Clayton (2007)IMDb ↗Lb ↗2Bill Simmons▶ 1:09:58

Directors Referenced (14)

NameLinksMentionsMentioned byKnown ForFirst
Alexander PayneIMDb ↗Lb ↗33Bill Simmons, Sean Fennessey, Chris RyanThe Descendants▶ 6:47
Will KistlerIMDb ↗Lb ↗12Bill Simmons, Sean FennesseyThe Incredible Hulk, Ant-Man▶ 20:18
Clint EastwoodIMDb ↗Lb ↗5Bill Simmons, Sean FennesseyMillion Dollar Baby, Gran Torino, Unforgiven▶ 27:37
Hal AshbyIMDb ↗Lb ↗5Sean Fennessey, Bill SimmonsIn the Heat of the Night, Harold and Maude▶ 6:53
Michael MannIMDb ↗Lb ↗4Sean Fennessey, Bill Simmons, Chris RyanThe Insider, Collateral, The Last of the Mohicans▶ 34:25
Kosta JokicIMDb ↗Lb ↗3Bill Simmons▶ 44:29
Taylor HackfordIMDb ↗Lb ↗3Chris Ryan, Bill Simmons▶ 34:25
Warren BeattyIMDb ↗Lb ↗3Bill SimmonsHeaven Can Wait▶ 54:13
Martin ScorseseIMDb ↗Lb ↗2Bill Simmons, Sean FennesseyTaxi Driver, Killers of the Flower Moon, Mean Streets▶ 27:37
Paul BellanyIMDb ↗Lb ↗2Sean Fennessey, Bill SimmonsStardust▶ 0:00
Claiborne LashleyIMDb ↗Lb ↗1Sean Fennessey▶ 1:39:22
Jason ReitmanIMDb ↗Lb ↗1Bill SimmonsUp in the Air, Thank You for Smoking▶ 8:26

Actors Referenced (76)

NameLinksMentionsMentioned byKnown ForFirst
Jack NicholsonIMDb ↗Lb ↗57Bill Simmons, Sean Fennessey, Chris RyanChinatown, As Good as It Gets, The Departed▶ 6:27
Paul GiamattiIMDb ↗Lb ↗36Sean Fennessey, Bill Simmons, Chris RyanSideways, Cinderella Man▶ 10:19
Felicien PinotIMDb ↗Lb ↗24Bill Simmons, Sean Fennessey, Chris Ryan▶ 16:46
Krista SaabIMDb ↗Lb ↗13Bill Simmons, Chris RyanAmerican Gangster▶ 1:00:30
Makabe GaneyIMDb ↗Lb ↗11Bill Simmons, Chris RyanJustice League, The Founder▶ 52:05
Daniel SeaIMDb ↗Lb ↗9Bill Simmons, Sean Fennessey▶ 20:04
Don JohnsonIMDb ↗Lb ↗7Bill Simmons, Chris RyanDjango Unchained▶ 1:46
Mike LeeIMDb ↗Lb ↗6Chris Ryan, Bill Simmons, Sean Fennessey▶ 5:20
Virginia MadsenIMDb ↗Lb ↗6Bill Simmons, Chris Ryan, Sean FennesseySideways▶ 30:46
Andy RichterIMDb ↗Lb ↗4Bill Simmons, Sean Fennessey▶ 1:45:07
Bill MurrayIMDb ↗Lb ↗3Chris Ryan, Sean FennesseyLost in Translation, Rushmore, Moonrise Kingdom▶ 4:19
Bob CousyIMDb ↗Lb ↗3Bill SimmonsBlue Chips▶ 4:29

Writers Referenced (4)

NameLinksMentionsMentioned byKnown ForFirst
Rex PickettIMDb ↗Lb ↗7Bill Simmons, Chris RyanSideways▶ 22:18
Brian KoppelmanIMDb ↗Lb ↗1Bill SimmonsRunaway Jury, Michael Clayton▶ 1:08:33
Harvey WeinsteinIMDb ↗Lb ↗1Sean FennesseyShakespeare in Love, The Hateful Eight▶ 31:36
William GoldmanIMDb ↗Lb ↗1Bill SimmonsButch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride▶ 1:37:45

Cinematographers Referenced (1)

NameLinksMentionsMentioned byKnown ForFirst
Christophe LegalIMDb ↗Lb ↗2Bill Simmons, Chris Ryan▶ 1:29:04