Wander through the financial district to get a feel for the bank heist of The Thomas Crown Affair, or visit Longfellow Bridge and Copley Square for a dose of cult classic The Boondock Saints.
In 1997, Good Will Hunting director Gus Van Sant placed two of his main actors -- then-unknowns Matt Damon and Ben Affleck, who co-wrote the screenplay which eventually won them their first Oscar -- in local Southie bar Woodie's L-Street Tavern. Other areas used include Harvard Square, the Public Garden, and Charlestown.
Clint Eastwood's Mystic River, which showcases acting heavyweights Sean Penn, Tim Robbins, and Kevin Bacon, filmed a rather poignant moment in Franklin Park. Boston-born author Dennis Lehane, who wrote the novel on which River was based, also penned Gone Baby Gone, which inspired Ben Affleck's directorial debut of the same name. The latter filmed in much of South Boston and Dorchester.
And of course, no Boston cinema chat is complete without Scorcese's heart-pounding remake The Departed, infused with the typical Boston accents that, while natural to Matt Damon and Mark Wahlberg, California-born Leonardo DiCaprio had to learn. The iconic rooftop scenes were shot in the Seaport District, the secret rendezvous under Neponset Bridge, the cat-and-mouse chase in Chinatown, and the end shootout in Quincy. For the domineering exterior shots of the police department, visit the Hurley Building on Staniford Street.
If the gritty realism of these stories starts to get to you, pop over to Beacon Street for a visit to the original Cheers location -- and find out if everybody really does know your name!