‘Sideways’ With Bill Simmons, Chris Ryan, and Sean Fennessey
January 10, 2023 · Sideways (2004) · Comedy · Drama · Romance · 1:49:00
Categories
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
Butch's Girlfriend Award
Bill SimmonsThe fake car accident, specifically putting the concrete brick on the gas pedal▶ 1:00:27
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
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 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'▶ 1:15:24
Chris RyanJessica Hecht — Jessica Hecht - noting she has won this award multiple times on the podcast▶ 1:16:04
Apex Mountain
Bill SimmonsPaul 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▶ 1:24:07
Chris RyanPaul Giamatti — Giamatti: John Adams over Billions; Sandra Oh: Killing Eve first season as potential apex▶ 1:24:05
Sean FennesseyThomas Haden Church — Thomas Hayden Church discussion but no clear yes/no position stated▶ 1:24:29
Hall of Fame Plaque
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
Is This Movie Better With
Bill SimmonsWayne Jenkins, Danny Trejo, Catherine Hahn, Steve Buscemi, Sam Jackson, JT Walsh▶ 1:35:01
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
Who Won the Movie
Bill SimmonsAlexander Payne — Alexander Payne - because this movie gave him lasting filmography appeal and made people buy 'season tickets' for his future films▶ 1:43:20
Chris RyanPaul Giamatti — Paul Giamatti - prevented him from being just a supporting actor for life and made him a leading man▶ 1:43:04
Sean FennesseyPaul Giamatti — Paul 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) | Links | Mentions | Mentioned by | First |
|---|---|---|---|---|
| Crank (2006) | IMDb ↗Lb ↗ | 7 | Bill Simmons, Chris Ryan | ▶ 52:02 |
| The Aviator (2004) | IMDb ↗Lb ↗ | 5 | Bill Simmons | ▶ 27:37 |
| The Beach (2000) | IMDb ↗Lb ↗ | 5 | Bill Simmons, Sean Fennessey | ▶ 12:11 |
| About Schmidt (2002) | IMDb ↗Lb ↗ | 4 | Bill Simmons, Sean Fennessey | ▶ 7:18 |
| Finding Neverland (2004) | IMDb ↗Lb ↗ | 4 | Bill Simmons, Sean Fennessey | ▶ 29:56 |
| Million Dollar Baby (2004) | IMDb ↗Lb ↗ | 4 | Bill Simmons | ▶ 27:32 |
| The Descendants (2011) | IMDb ↗Lb ↗ | 3 | Bill Simmons, Sean Fennessey | ▶ 23:33 |
| Before Sunset (2004) | IMDb ↗Lb ↗ | 2 | Bill Simmons, Sean Fennessey | ▶ 28:39 |
| Casino (1995) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 1:34:06 |
| Fargo (1996) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 26:55 |
| Groundhog Day (1993) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 4:25 |
| Michael Clayton (2007) | IMDb ↗Lb ↗ | 2 | Bill Simmons | ▶ 1:09:58 |
Directors Referenced (14)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Alexander Payne | IMDb ↗Lb ↗ | 33 | Bill Simmons, Sean Fennessey, Chris Ryan | The Descendants | ▶ 6:47 |
| Will Kistler | IMDb ↗Lb ↗ | 12 | Bill Simmons, Sean Fennessey | The Incredible Hulk, Ant-Man | ▶ 20:18 |
| Clint Eastwood | IMDb ↗Lb ↗ | 5 | Bill Simmons, Sean Fennessey | Million Dollar Baby, Gran Torino, Unforgiven | ▶ 27:37 |
| Hal Ashby | IMDb ↗Lb ↗ | 5 | Sean Fennessey, Bill Simmons | In the Heat of the Night, Harold and Maude | ▶ 6:53 |
| Michael Mann | IMDb ↗Lb ↗ | 4 | Sean Fennessey, Bill Simmons, Chris Ryan | The Insider, Collateral, The Last of the Mohicans | ▶ 34:25 |
| Kosta Jokic | IMDb ↗Lb ↗ | 3 | Bill Simmons | ▶ 44:29 | |
| Taylor Hackford | IMDb ↗Lb ↗ | 3 | Chris Ryan, Bill Simmons | ▶ 34:25 | |
| Warren Beatty | IMDb ↗Lb ↗ | 3 | Bill Simmons | Heaven Can Wait | ▶ 54:13 |
| Martin Scorsese | IMDb ↗Lb ↗ | 2 | Bill Simmons, Sean Fennessey | Taxi Driver, Killers of the Flower Moon, Mean Streets | ▶ 27:37 |
| Paul Bellany | IMDb ↗Lb ↗ | 2 | Sean Fennessey, Bill Simmons | Stardust | ▶ 0:00 |
| Claiborne Lashley | IMDb ↗Lb ↗ | 1 | Sean Fennessey | ▶ 1:39:22 | |
| Jason Reitman | IMDb ↗Lb ↗ | 1 | Bill Simmons | Up in the Air, Thank You for Smoking | ▶ 8:26 |
Actors Referenced (76)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Jack Nicholson | IMDb ↗Lb ↗ | 57 | Bill Simmons, Sean Fennessey, Chris Ryan | Chinatown, As Good as It Gets, The Departed | ▶ 6:27 |
| Paul Giamatti | IMDb ↗Lb ↗ | 36 | Sean Fennessey, Bill Simmons, Chris Ryan | Sideways, Cinderella Man | ▶ 10:19 |
| Felicien Pinot | IMDb ↗Lb ↗ | 24 | Bill Simmons, Sean Fennessey, Chris Ryan | ▶ 16:46 | |
| Krista Saab | IMDb ↗Lb ↗ | 13 | Bill Simmons, Chris Ryan | American Gangster | ▶ 1:00:30 |
| Makabe Ganey | IMDb ↗Lb ↗ | 11 | Bill Simmons, Chris Ryan | Justice League, The Founder | ▶ 52:05 |
| Daniel Sea | IMDb ↗Lb ↗ | 9 | Bill Simmons, Sean Fennessey | ▶ 20:04 | |
| Don Johnson | IMDb ↗Lb ↗ | 7 | Bill Simmons, Chris Ryan | Django Unchained | ▶ 1:46 |
| Mike Lee | IMDb ↗Lb ↗ | 6 | Chris Ryan, Bill Simmons, Sean Fennessey | ▶ 5:20 | |
| Virginia Madsen | IMDb ↗Lb ↗ | 6 | Bill Simmons, Chris Ryan, Sean Fennessey | Sideways | ▶ 30:46 |
| Andy Richter | IMDb ↗Lb ↗ | 4 | Bill Simmons, Sean Fennessey | ▶ 1:45:07 | |
| Bill Murray | IMDb ↗Lb ↗ | 3 | Chris Ryan, Sean Fennessey | Lost in Translation, Rushmore, Moonrise Kingdom | ▶ 4:19 |
| Bob Cousy | IMDb ↗Lb ↗ | 3 | Bill Simmons | Blue Chips | ▶ 4:29 |
Writers Referenced (4)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Rex Pickett | IMDb ↗Lb ↗ | 7 | Bill Simmons, Chris Ryan | Sideways | ▶ 22:18 |
| Brian Koppelman | IMDb ↗Lb ↗ | 1 | Bill Simmons | Runaway Jury, Michael Clayton | ▶ 1:08:33 |
| Harvey Weinstein | IMDb ↗Lb ↗ | 1 | Sean Fennessey | Shakespeare in Love, The Hateful Eight | ▶ 31:36 |
| William Goldman | IMDb ↗Lb ↗ | 1 | Bill Simmons | Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride | ▶ 1:37:45 |
Cinematographers Referenced (1)
| Name | Links | Mentions | Mentioned by | Known For | First |
|---|---|---|---|---|---|
| Christophe Legal | IMDb ↗Lb ↗ | 2 | Bill Simmons, Chris Ryan | ▶ 1:29:04 |