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Every year on Podcast Like It’s the 2000s, Phil and Emily pick one Chaos Pick a movie that doesn’t quite fit into any miniseries, but demands to be talked about anyway. This year’s selection is Sky Captain and the World of Tomorrow, the ambitious 2004 pulp-sci-fi experiment that looked like the future of filmmaking… and then quietly disappeared.Joining the conversation is Emma Stefansky, here to passionately defend Kerry Conran’s retro-futurist spectacle starring Jude Law, Gwyneth Paltrow, and Angelina Jolie. The group digs into the film’s groundbreaking all-digital production, its sepia-toned visual language, and why it feels like a volume-stage movie years before volume stages became standard. They also explore how Sky Captain fits into a lineage of stylized adventure films like Dick Tracy and The Rocketeer, and why audiences often remember how the movie looked more than what actually happens in it.Along the way, they discuss Roger Ebert’s glowing four-star review, the film’s middling box office and critical afterlife, the risks of resurrecting actors digitally, and whether Sky Captain is a misunderstood cult object or simply a fascinating near-miss. It’s a conversation about ambition, technology, and the strange movies that briefly convince us we’re looking at the future right before the future changes again.

We close out our holiday run It’s Christmas and the Boys Are Sad with Martin McDonagh’s In Bruges, a film that balances brutal violence, pitch-black comedy, and unexpected tenderness against a fairy-tale Christmas backdrop. Phil & Emily joined by writers and podcasters Clay Keller and Alan Sepinwall to unpack why this movie has only grown more beloved and more emotionally complicated over time.The conversation dives into Colin Farrell’s career-defining performance, Brendan Gleeson’s quiet moral gravity, and Ralph Fiennes’ volcanic late-movie entrance. They explore McDonagh’s dialogue rhythms, the film’s strange tonal alchemy, and how Bruges itself becomes a purgatorial space beautiful, frozen in time, and quietly judgmental. Christmas lights, medieval towers, and European pageantry all heighten the sense that these characters are stuck between punishment and absolution.They also discuss the movie’s reputation shift from cult hit to modern classic, its placement within McDonagh’s broader body of work, and why In Bruges may be the most emotionally honest entry in the “sad men at Christmas” cinematic canon. Along the way, the group touches on Carter Burwell’s melancholic score, the film’s theatrical release context, and the way humor is used as both shield and confession.Whether you first saw In Bruges in theaters or came to it years later through word of mouth, this episode examines why the film still hits so hard and why it remains one of the defining dark comedies of the 2000s.

Our holiday miniseries It’s Christmas and the Boys Are Sad continues with Steven Spielberg’s Catch Me If You Can, a movie that feels breezy and charming on the surface and quietly devastating underneath. Phil and Emily are joined by author, video essayist, and YouTuber Lindsay Ellis to unpack why this film has only grown richer with time.The conversation explores the movie’s deceptive simplicity, Leonardo DiCaprio’s performance as a teenager performing adulthood, and Tom Hanks’ unusually vulnerable turn as an FBI agent defined by routine, loneliness, and obsession. They dig into Spielberg’s immaculate craft from match editing to tone control and why the film often gets overlooked in discussions of his “serious” work.They also discuss the film’s Christmas framing, its melancholy view of masculinity and authority, and how its themes of fraud, bureaucracy, and institutional power feel more prescient now than they did in 2002. Along the way, the trio debates the movie’s length, its cultural reception, and why Catch Me If You Can plays like a con movie that slowly reveals itself to be about divorce, abandonment, and the quiet cruelty of systems.Whether you remember it as a slick crowd-pleaser or are revisiting it for the first time, this episode reframes Catch Me If You Can as one of Spielberg’s most emotionally layered films of the 2000s and a perfect fit for a sad-boys Christmas.

Our 2000s Holiday Noir miniseries kicks off with a film that helped relaunch Robert Downey Jr.’s career and reintroduced Shane Black to a new generation: Kiss Kiss Bang Bang. Phil and Emily are joined by film critic and historian Alonso Duralde to unpack why this meta-crime-comedy still feels like lightning in a bottle.The trio digs into the movie’s razor-sharp script, its chaotic but affectionate relationship to noir, and the way Shane Black balances darkness with a wink. They explore Michelle Monaghan’s standout performance, Val Kilmer’s iconic turn as Gay Perry, and what made this moment in RDJ’s career so precarious and so thrilling.They also dive into the film’s tone-shifting structure, its overplotted charm, its self-aware narration, and why the movie’s emotional core sneaks up on you. Along the way, they talk Shane Black’s imitators, the difficulty of pulling off postmodern genre homage, and how this film manages to love the very tropes it skewers. Whether Kiss Kiss Bang Bang has been a long-time favorite or a movie you somehow missed, this episode revisits the 2005 cult classic with fresh eyes, big laughs, and a deep appreciation for what makes it so deceptively tricky and so rewatchable.

Our Mike Nichols 2000s miniseries continues with one of the director’s strangest career anomalies: Charlie Wilson’s War. Phil and Emily are joined by critic and writer Sonia Saraiya to unpack how Nichols, Aaron Sorkin, Tom Hanks, and Julia Roberts came together to make a political dramedy that feels breezy on the surface but carries enormous historical weight underneath.The conversation digs into the true story behind the film Charlie Wilson, Joanne Herring, and CIA operative Gust Avrakotos and how their covert efforts armed Afghan fighters during the Soviet Afghan War. Phil breaks down the film’s compressed narrative and its reluctance to grapple with the long-term consequences of U.S. involvement, including the geopolitical chain reaction the movie only gestures toward. Sonia and Emily explore Sorkin’s ideology, the movie’s softened satire, and how the adaptation diverged from the darker, sharper script Nichols originally signed onto.From Philip Seymour Hoffman’s electric performance to Nichols’ complicated, last-years-of-his-career filmmaking context, the episode traces how the movie became both an accessible studio comedy and a missed opportunity for deeper political reckoning. They also examine the infamous alternate ending, Nichols’ battle over the cut, and the creative tug-of-war between Hanks, Sorkin, and the studio.Whether you’ve revisited Charlie Wilson’s War recently or haven’t thought about it since 2007, this episode highlights why the film is entertaining, frustrating, and uniquely revealing about the final chapter of Mike Nichols’ film career.

This week, we continue our Mike Nichols miniseries with a deep dive into Closer (2004), joined by Sean Fennessey of The Big Picture. It’s a film that captivated many of us in our early 20s only to unravel under rewatch with age, perspective, and healthier emotional boundaries.We unpack why Closer once felt like “grown-up cinema,” how its theatrical origins shape its structure, and why its four leads Julia Roberts, Jude Law, Natalie Portman, and Clive Owen are all performing at maximum intensity inside a script that might not deserve them. From the infamous strip-club scene to the messy power dynamics, contradictions, and emotional violence embedded in Patrick Marber’s writing, we ask the question: does any of this actually work?Sean brings insight into Nichols’ career, the film’s mid-2000s cultural footprint (including its unexpected influence on emo/screamo lyrics), and the era’s attempt to manufacture Jude Law into Hollywood’s next megastar. And yes, we talk about Damien Rice, the Oscars, and why Closer remains a fascinating artistic contradiction: a film full of great performances inside a story that collapses under scrutiny.

In the conclusion to their Mike Nichols miniseries, Phil and Emily welcome Joe Reid (Vulture, This Had Oscar Buzz) to unpack Angels in America: Part Two Perestroika.The trio dives deep into how Nichols translated Tony Kushner’s monumental stage play into one of HBO’s most ambitious miniseries exploring its themes of prophecy, identity, queer resilience, and the intersection of politics and spirituality in 1980s America. They discuss the legacy of Angels as both a masterpiece of television and a cultural turning point for the medium itself, its sweeping performances from Meryl Streep, Al Pacino, and Mary-Louise Parker, and how Nichols closed out his career redefining prestige TV.This episode caps a thoughtful look back at Nichols’ 2000s work, from Wit to Angels in America, examining how he brought cinematic intimacy to television storytelling.

This week on Podcast Like It’s The 2000s, Phil and Emily begin their deep dive into Mike Nichols’ monumental HBO miniseries, Angels in America with special guest Adam B. Vary (Variety).Together, they unpack Tony Kushner’s sweeping adaptation of his Pulitzer Prize winning play, exploring how Nichols brought the AIDS crisis, politics, and spirituality to television with raw emotional power. From Meryl Streep’s transformative performance to Al Pacino’s chilling portrayal of Roy Cohn, the trio explores the artistry, ambition, and legacy of a project that redefined what prestige TV could be.They also discuss how Angels in America marked the pinnacle of HBO’s early 2000s dominance, bridging the era between The Sopranos and Six Feet Under and setting the tone for the next two decades of prestige television.If you want to hear Part 2, full video episodes, and exclusive behind-the-scenes conversations, join the Podcast Like It’s Patreon community for more. 🌈 👉 patreon.com/PodcastLikeIts

This week on Podcast Like It’s The 2000s, Phil and Emily welcome writer Emily Hughes to discuss Paranormal Activity — the micro-budget phenomenon that redefined horror for a generation. Together they dig into the film’s scrappy origins, the ingenious use of found footage to build dread, and how Oren Peli’s minimalist approach reshaped studio thinking about what a blockbuster could be.From its DIY filmmaking roots to its massive cultural impact, the conversation examines why Paranormal Activity remains one of the most effective and influential horror movies of the 2000s — and how it kicked off a wave of imitators that could never quite match its eerie simplicity.If you want to watch the full video of this conversation, hear bonus episodes, and access exclusive mini-series and behind-the-scenes content, join the Podcast Like It’s Patreon community for all that and more. 👻 👉 patreon.com/PodcastLikeIts