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.

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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.

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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.

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