Movie of the Year: 2006The Departed (feat Adam Kempenaar!)Inside The Departed Podcast EpisodeWelcome to The Departed podcast episode of Movie of the Year: 2006, where the Taste Buds take on Martin Scorsese's Boston crime epic. Ryan, Mike, and Greg welcome Filmspotting co-host Adam Kempenaar to the panel. Together, they dig into a film about cops, crooks, and the men who raise them. Moreover, the conversation covers fatherhood, gender, and the rough racial politics of Scorsese's South Boston. Additionally, the crew delivers a Career Retrospective on Leonardo DiCaprio, the jittery star at the film's center. Ultimately, the episode asks whether this Best Picture winner still earns its reputation twenty years later. New to the season? Start with our Movie of the Year 2006 intro episode, then catch up on the full 2006 bracket reveal. About the Film: The Departed (2006)The Departed opened in theaters on October 6, 2006. Martin Scorsese directed, and William Monahan wrote the screenplay. Specifically, Monahan adapted the 2002 Hong Kong thriller Infernal Affairs. The story follows two moles working on opposite sides of the law. Leonardo DiCaprio plays Billy Costigan, an undercover cop inside the Irish mob. Meanwhile, Matt Damon plays Colin Sullivan, a mob plant rising through the Massachusetts State Police. Jack Nicholson rules over both men as crime boss Frank Costello. Notably, the supporting cast includes Mark Wahlberg, Martin Sheen, Vera Farmiga, Alec Baldwin, and Ray Winstone. The film became a major critical and commercial hit, earning more than $290 million worldwide. In addition, it won four Academy Awards, including Best Picture and Best Adapted Screenplay. Scorsese finally won Best Director after five earlier nominations. Thelma Schoonmaker also took home Best Film Editing. Roger Ebert gave the film four stars in his original RogerEbert.com review. For full cast and crew credits, visit The Departed on IMDb. Guest Panelist: Adam KempenaarAdam Kempenaar co-founded Filmspotting, one of the longest-running film podcasts in the medium. He launched the show in March 2005 with Sam Van Hallgren. Since 2012, he has co-hosted alongside Josh Larsen. Filmspotting has now passed 1,000 episodes and has also aired on WBEZ in Chicago. Furthermore, Kempenaar teaches at the University of Iowa, where his courses cover film criticism, sports and cinema, and podcasting. He is also a longtime member of the Chicago Film Critics Association. Additionally, he consults on marketing and content for the Chicago International Film Festival. For twenty years, he also led marketing and content for the Chicago Blackhawks. In 2025, he and Larsen celebrated two decades of the show with the first Filmspotting Fest in Chicago. Notably, Filmspotting was barely a year old when The Departed opened. That timing gives Adam a rare firsthand view of the 2006 film conversation. Find his reviews, Top 5 lists, and Sacred Cow episodes at filmspotting.net. Father Figures on The Departed PodcastFathers haunt every corner of The Departed. Costello grooms young Colin Sullivan from childhood, handing him groceries and shaping his loyalty. By contrast, Billy Costigan grows up with a dead father and a family split between Southie and the North Shore. Captain Queenan, played by Martin Sheen, becomes the steady parent Billy never had. Consequently, Queenan's death lands as the emotional turning point of the film. Meanwhile, Sullivan chases approval from every authority figure around him, from Costello to Ellerby. The film even closes on an open paternity question surrounding Madolyn's pregnancy. The panel digs into how Monahan's script treats the police and the mob as rival families. In practice, both institutions recruit sons, reward obedience, and punish betrayal. Above all, the Taste Buds and Adam ask which surrogate father does the most damage. Gender and Masculinity in The DepartedThe Departed is a crowded film about men performing toughness. Cops trade insults about each other's mothers, sexuality, and manhood. Costello, meanwhile, treats women as property and punchlines. Against that backdrop, Vera Farmiga's Madolyn stands nearly alone as a major female character. Interestingly, Monahan built her from two separate women in Infernal Affairs, one for each mole. As a result, she becomes the hinge between Billy and Colin. That choice raises real questions for the panel. Is Madolyn a fully realized character, or a device that links the two leads? Additionally, the crew considers how Sullivan's private failures mirror his fractured identity. The conversation also weighs whether Scorsese critiques this macho culture or simply enjoys it. Boston, Race, and Tribalism: The Departed 2006 Podcast DebateScorsese sets his story in South Boston, a neighborhood with a fraught racial history. Costello opens the film with a monologue about the Irish, the Italians, and Black Bostonians. Throughout the film, characters toss slurs as casually as they throw punches. Nevertheless, the panel debates what the film actually says about that bigotry. On one hand, the dialogue captures the tribal loyalties behind decades of city tension, including the 1970s busing crisis. On the other hand, some viewers argue the film treats ethnic insults as local color rather than subject. Furthermore, Costello's crew and the state police both run on in-group loyalty and suspicion of outsiders. Therefore, that tribalism powers the entire mole plot. The Taste Buds and Adam ask whether the film interrogates Boston's prejudices or leans on them for authenticity. Career Retrospective: Leonardo DiCaprioThis episode also features a Career Retrospective on Leonardo DiCaprio. The Departed marked his third collaboration with Scorsese, following Gangs of New York and The Aviator. Notably, 2006 was a banner year for him, and Blood Diamond earned him a Best Actor nomination that season. His early work stretches from This Boy's Life and What's Eating Gilbert Grape to Titanic. Later highlights include Catch Me If You Can, Inception, Django Unchained, and The Wolf of Wall Street. DiCaprio finally won the Best Actor Oscar for The Revenant. Since then, he has worked again with Quentin Tarantino, Scorsese, and Paul Thomas Anderson. In total, he has made six feature films with Scorsese. The panel walks through the full filmography, from child actor to elder statesman. However, you will have to listen to hear how the Taste Buds and Adam rank his work. Why The Departed Still MattersThe Departed endures as the film that finally won Scorsese his Oscar. Moreover, it proved a Hollywood remake of a Hong Kong crime film could stand on its own. Its double-agent structure still echoes through crime thrillers and prestige television. Additionally, its performances remain endlessly quotable, especially Wahlberg's profane Sergeant Dignam. Alongside Mystic River and Gone Baby Gone, it helped define the Boston crime cycle of the 2000s. Ultimately, the film still sparks arguments about Scorsese's best work. Those arguments make it perfect bracket material for Movie of the Year: 2006. Related Episodes from Movie of the Year: 2006Movie of the Year 2006: Intro Part 1The Movies of 2006 Bracket Reveal2006 Mixtape Part IBrowse every Movie of the Year episode FAQ: The Departed Podcast and FilmWhat is The Departed podcast episode about?This Movie of the Year: 2006 episode features the Taste Buds and guest Adam Kempenaar discussing Martin Scorsese's The Departed. Topics include father figures, gender, and the film's portrait of race in Boston. The episode also includes a Leonardo DiCaprio Career Retrospective. What is The Departed about?The Departed follows two moles in Boston. Billy Costigan goes undercover inside Frank Costello's Irish mob. Meanwhile, Colin Sullivan secretly works for Costello inside the Massachusetts State Police. Each man races to expose the other first. Who directed The Departed?Martin Scorsese directed The Departed. William Monahan wrote the screenplay, and the film won Scorsese his first Academy Award for Best Director. Is The Departed based on a true story?No, the plot comes from the 2002 Hong Kong film Infernal Affairs. However, Jack Nicholson's Frank Costello draws loose inspiration from real Boston gangster Whitey Bulger. Did The Departed win Best Picture?Yes. The Departed won Best Picture at the 79th Academy Awards. It also
