October marks the 20th anniversary of the release of Martin Scorsese’s “The Departed,” a film widely regarded as a defining entry in the Boston crime genre. The movie, loosely based on the criminal exploits of notorious mob figure Whitey Bulger, has sparked enduring debate among cinephiles about its place in the pantheon of Boston-centered films.

Released in 2006, “The Departed” earned critical acclaim and won Scorsese his first Academy Award for Best Director. The ensemble cast, featuring Leonardo DiCaprio, Matt Damon, Jack Nicholson, and Mark Wahlberg, brought to life a tense narrative of undercover operations and mafia infiltration. The film’s gritty portrayal of Boston’s criminal underworld, combined with Scorsese’s trademark direction, led many to hail it not only as the best crime movie set in the city but, for some, the best Boston film overall.

However, the film’s status is not without dissent. Some critics and local aficionados argue that it does not capture the city’s essence as authentically as other works, pointing in particular to Ben Affleck’s 2010 film “The Town.” Set in Boston’s Charlestown neighborhood, “The Town” offers a more intimate look at local characters and culture, which some viewers find resonates more genuinely with the city’s identity.

This divergence in opinion highlights a broader discussion about how film captures the complexities of place and history. While “The Departed” remains a commercial and critical milestone in Boston cinema, the ongoing conversation underscores the subjective nature of ranking films within a local context. Whether viewed as the definitive Boston crime story or simply a formidable entry in the genre, “The Departed” continues to provoke reflection and debate two decades after its debut.