- 1 hour 47 minutes93: Where the Wild Things Are with Drew McWeeny
Phil and Emily are joined by film critic, screenwriter, and Hip Pocket podcast host Drew McWeeny to discuss Where the Wild Things Are (2009), the Spike Jonze adaptation of Maurice Sendak's 85-word picture book that cost roughly $100 million, barely broke even, got one Blu-ray release, and has been sitting in a strange kind of limbo ever since.
Drew has been close to this film longer than almost anyone outside the production. He saw a rough cut in Pasadena before a single effects shot was completed, got a personal call from Legendary Pictures founder Thomas Tull asking for his honest reaction, and later sat down with Spike Jonze himself for two hours as the film fought to find its finish line. Phil thinks it's a miracle it exists at all. Emily finds it formally audacious and sometimes frustrating in equal measure. Drew thinks it's a great film. He also thinks it might not be a film for children.
The three dig into the full production story, from the Jim Henson Company's 50-pound creature heads that got scrapped six weeks before filming to Spike's decision to shoot everything handheld with no green screens and no tracking dots on any of the creatures. They talk about why James Gandolfini was the perfect choice for Carol, what the voice cast recorded running around a black box theater instead of isolated booths, and what it means to watch this movie as a parent who has been the angry one in the room.
This episode wraps up the show's Spike Jonze and Charlie Kaufman miniseries, following Adaptation and Synecdoche, New York.
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Podcast Like It's 2000s — https://www.instagram.com/podcastlikeits2000s
Phil Iscove — https://www.instagram.com/pmiscove
Emily St. James — https://www.instagram.com/emilystjams
Drew McWeeny — https://www.instagram.com/drewmcweeny
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8 May 2026, 7:00 am - 1 hour 37 minutes92: Synecdoche, New York with Angie Han
Phil and Emily are joined by Angie Han, TV critic at The Hollywood Reporter, to discuss Synecdoche, NY (2008), Charlie Kaufman's audacious directorial debut and the film Roger Ebert called the best of the 2000s.
Kaufman wrote and directed this hallucinatory portrait of Caden Cotard (Philip Seymour Hoffman), an ailing theater director who uses a MacArthur Fellowship to build a life-size replica of New York City inside a warehouse. As the decades pass and his art consumes his life, the film tunnels deeper into mortality, creative obsession, and the quiet horror of living in a body that won't cooperate. Originally conceived as a horror film with Spike Jonze, Synecdoche, NY opened in October 2008 against High School Musical 3 and Saw 5, made $4.5 million on a $20 million budget, and has since been ranked among the greatest films of the 21st century by the BBC, the Guardian, and Time.
Phil finds it deeply triggering as a self-described hypochondriac. Angie has seen it a dozen times and finds it weirdly soothing. Emily thinks it's funnier than people give it credit for. All three dig into why this film bombed commercially and became a critical touchstone, what it means to watch it in your 20s versus your 40s, and why it still doesn't have a Criterion edition.
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Emily St. James — https://www.instagram.com/emilystjams
Angie Han — https://www.instagram.com/ajhan06
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1 May 2026, 7:00 am - 1 hour 34 minutes91: Eternal Sunshine of the Spotless Mind with Katey Rich
Phil and Emily are joined by Katey Rich, awards editor at The Ankler and host of the Prestige Junkie podcast, to discuss Eternal Sunshine of the Spotless Mind (2004), Michel Gondry's Charlie Kaufman-written love story and one of the defining films of its generation. This episode is part of the ongoing miniseries on the 2000s films of Charlie Kaufman and Michel Gondry.
Jim Carrey plays Joel and Kate Winslet plays Clementine, former partners who independently undergo a procedure to erase each other from their memories. The film also stars Tom Wilkinson, Mark Ruffalo, Kirsten Dunst, and Elijah Wood. Released March 19th, 2004, it opened against Dawn of the Dead, The Passion of the Christ, and Starsky and Hutch, earned only two Oscar nominations, and somehow still became Charlie Kaufman's highest-grossing film.
Phil, Emily, and Katey dig into how a movie that felt like a March dump release became a Sight and Sound list entry and a Letterboxd top 5 staple, why the Academy of 2004 simply wasn't ready for it, and how Jim Carrey managed to get overlooked by Oscar voters again six years after The Truman Show. They also get into how the Gondry and Kaufman collaboration works so much better here than it did on Human Nature, what the ending means when you come back to it older, and why Everything Everywhere All At Once couldn't exist without this film.
Katey saw it right after her first real breakup and was completely walloped by it. Emily has seen it over ten times and has been happily married since college. Phil was 24 when it came out and was in exactly the right kind of romantic chaos for it to hit hardest. Three very different relationships with the same movie.
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Phil Iscove: https://www.instagram.com/pmiscove
Emily St. James: https://www.instagram.com/emilystjams
Katey Rich: https://www.instagram.com/kateyrichtalking
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24 April 2026, 7:00 am - 1 hour 35 minutes90: Confessions of a Dangerous Mind with Jason Bailey
Phil and Emily are joined by film critic and author Jason Bailey to revisit Confessions of a Dangerous Mind, George Clooney's 2002 directorial debut based on Chuck Barris' unauthorized autobiography. Jason is the author of Gandolfini: The Real Life of the Man Who Made Tony Soprano, now available in paperback.
Chuck Barris created The Dating Game and The Gong Show. He also claimed to have secretly killed 33 people for the CIA. Charlie Kaufman wrote the screenplay, Sam Rockwell stars as Barris, and Drew Barrymore and Julia Roberts co-star. Before Clooney made it, the film passed through David Fincher, Darren Aronofsky, Sam Mendes, Bryan Singer, Johnny Depp, Ben Stiller, Sean Penn, and Mike Myers over nearly a decade of development.
The three dig into what Clooney kept and what he stripped from Kaufman's original script, whether Sam Rockwell's performance holds the whole thing together, and what Roberts and Barrymore bring to a film that never quite commits to its own tonal chaos. They also get into Clooney's arc as a director, a genuinely promising debut followed by a filmography of diminishing returns, and whether Confessions of a Dangerous Mind holds up as his most interesting work two decades on.
Jason says yes, unequivocally. Emily loved it then and is reconsidering. Phil never fully clicked with it. They all agree the ending is something close to perfect.+
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Phil Iscove: https://www.instagram.com/pmiscove
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Jason Bailey: https://www.instagram.com/jasondashbailey
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17 April 2026, 7:00 am - 1 hour 36 minutes89: Adaptation with David Iserson & Dana Schwartz
This week on Podcast Like It’s the 2000s, Phil Iscove is joined by writer David Iserson (Ponies) and author/podcaster Dana Schwartz (Noble Blood, Anatomy: A Love Story) to unpack one of the most inventive films of the decade: Adaptation.
Part of our Spike Jonze & Charlie Kaufman mini-series, the group explores Kaufman’s famously meta screenplay, Nicolas Cage’s dual performance as Charlie and Donald Kaufman, and how the film turns writer’s block into one of the most daring Hollywood movies of the early 2000s. They also discuss the film’s wild journey from Susan Orlean’s The Orchid Thief to the screen, along with unforgettable supporting turns from Meryl Streep and Chris Cooper.
A deep dive into creativity, storytelling, and one of the strangest Oscar-winning screenplays ever written.
Podcast Like It’s the 2000s is a weekly podcast revisiting the movies, culture, and filmmaking that defined the decade.
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Podcast Like It's... - https://www.instagram.com/podcastlikeits
Phil Iscove - https://www.instagram.com/pmiscove
Emily St. James - https://www.instagram.com/emilystjams
David Iserson - https://www.instagram.com/davidiserson
Dana Schwartz - https://www.instagram.com/danaschwartzzz
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10 April 2026, 7:00 am - 1 hour 38 minutes88: Human Nature with Colby Day
Phil and Emily are joined by Colby Day to discuss Human Nature (2001), Michel Gondry's feature directorial debut and Charlie Kaufman's second produced screenplay. The trio dives into this offbeat comedy about a woman with hypertrichosis, a scientist obsessed with teaching table manners to mice, and a feral man raised in the wild. They explore how Kaufman and Gondry use this absurd love triangle to interrogate what it means to be "civilized." They also discuss the film's place in the early-2000s Kaufman canon, how it compares to Gondry and Kaufman's later collaboration Eternal Sunshine of the Spotless Mind, and why this strange, underseen comedy deserves a second look. Plus Tim Robbins as a 35-year-old virgin, Patricia Arquette's full-body hair, and Rhys Ifans eating with his hands at a fancy dinner.
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Phil Iscove - https://www.instagram.com/pmiscove
Emily St. James - https://www.instagram.com/emilystjams
Colby Day - https://www.instagram.com/thecolbyday
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2 April 2026, 7:00 am - 2 hours 3 minutes87: For Your Consideration with Adam B. Vary
Phil and Emily are joined by Adam B. Vary to discuss For Your Consideration (2006), Christopher Guest’s razor-sharp satire of Hollywood awards campaigns and the strange machinery behind Oscar buzz. As actors, publicists, and studios chase nominations, the film hilariously exposes how quickly hype can spiral into ego, anxiety, and manufactured prestige.
This episode also wraps up our brief three-film Christopher Guest 2000s miniseries, looking at how Guest’s mockumentary style evolved from Best in Show and A Mighty Wind into one of the most biting Hollywood satires of the decade.
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Phil Iscove - Instagram: @pmiscove
Emily St. James - Instagram: @emilystjams
Adam B. Vary - Instagram: @adambvary
Podcast Like It’s… Instagram: @podcastlikeits
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27 March 2026, 7:00 am - 1 hour 33 minutes86: A Mighty Wind with Carrie Courogen
This week on Podcast Like It’s the 2000s, Phil and Emily continue their Christopher Guest 2000s miniseries with A Mighty Wind, joined by writer and author Carrie Courogen.
They break down Guest’s uniquely gentle mockumentary style, the film’s satirical take on folk music culture, and why its characters feel both absurd and deeply human. Plus, a closer look at the performances, the emotional undercurrent beneath the comedy, and how A Mighty Wind fits within Guest’s larger body of work.
Phil also provides context for listeners on the film’s premise following three folk groups reuniting for a tribute concert highlighting its blend of nostalgia, melancholy, and humor.
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Phil Iscove: https://www.instagram.com/pmiscove
Emily St. James: https://www.instagram.com/emilystjams
Carrie Courogen: https://www.instagram.com/carriecourogen
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20 March 2026, 7:00 am - 1 hour 19 minutes85: Best in Show with Kathryn VanArendonk
Phil and Emily continue their journey through the 2000s with Christopher Guest’s beloved mockumentary Best in Show. Joined by critic Kathryn VanArendonk, they discuss the film’s improvisational comedy, its incredible ensemble cast—including Catherine O’Hara, Eugene Levy, Parker Posey, and Fred Willard—and why the world of competitive dog shows created one of the funniest comedies of the decade. They also unpack Guest’s unique filmmaking style and how Best in Show became a cult favorite that still influences comedy today.
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Phil Iscove — https://instagram.com/pmiscove
Emily St. James — https://instagram.com/emilystjams
Kathryn VanArendonk — https://www.instagram.com/kvanarendonk
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13 March 2026, 7:00 am - 1 hour 51 minutes84: Up with Josh Spiegel & Scott Renshaw
On this episode of Podcast Like It’s the 2000s, Phil and Emily are joined by film critics Josh Spiegel and Scott Renshaw to discuss Pixar’s emotional adventure about Carl Fredricksen, a widowed balloon salesman who lifts his house into the sky in search of Paradise Falls only to discover an unexpected stowaway along the way.
The group breaks down the film’s famous opening montage, its unusual elderly protagonist, and why Up represents a key moment in Pixar’s late-2000s creative peak. They also explore the movie’s legacy, its Best Picture nomination, and why its blend of grief, humor, and adventure still resonates.
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Podcast Like It’s…
Instagram: https://www.instagram.com/podcastlikeits/
Phil Iscove
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Emily St. James
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Josh Spiegel & Scott Renshaw Podcast:
Mousterpiece Melodies
https://mousterpiecemelodies.podbean.com/
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6 March 2026, 8:00 am - 2 hours 3 minutes83: Wall-E with Justin & Laura Khoo
Phil Iscove and Emily St. James continue their Pixar 2000s miniseries with a deep dive into WALL·E, Andrew Stanton’s 2008 animated sci-fi romance about a lonely trash-compacting robot left behind on Earth.
Joined by Justin and Laura Khoo, they break down the film’s near-silent first act, Ben Burtt’s groundbreaking sound design, the Axiom’s consumerist dystopia, and why WALL·E may be Pixar’s most political film. They also discuss its environmental themes, visual storytelling, and how it fits alongside Finding Nemo, The Incredibles, Ratatouille, and Cars in Pixar’s golden era.
Is WALL·E the studio’s boldest experiment? Its purest love story? Or both?
Follow the Hosts & Guests
Podcast Like It’s
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Phil Iscove
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Emily St. James
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Justin Khoo
Instagram: https://www.instagram.com/juskhoo
Laura Khoo
Instagram: https://www.instagram.com/laurajeanettekhoo
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