Still sharp: Jon Hamm’s star-studded crime thriller is almost perfect

Some films just vanish after a couple of years, don’t they? The ones you watch, vaguely rate, then forget ever existed. But every now and again, you stumble across a standout—one stacked with proper talent, razor-sharp writing, and the sort of intensity that makes you keep thinking about it years after. Case in point: The Town. Sixteen years on from its release, Ben Affleck’s Boston heist thriller hasn’t lost its edge, and frankly, still delivers better than half the so-called “crime classics” people bang on about these days.

The Town landed in 2010 and is still going strong with a 92% score on Rotten Tomatoes — not bad for a second-time director.

Affleck's Big Swing

By the time Affleck decided to direct (again) and co-write The Town, he wasn’t exactly basking in cinematic glory. Sure, he’d picked up goodwill as an actor off the back of Good Will Hunting and played about with some oddball Kevin Smith stuff—but let's be honest, the years before hadn’t been pretty, with stuff like Surviving Christmas and Man About Town nearly derailing him completely. Luckily, his directorial debut, Gone Baby Gone, showed he actually knew what he was doing from behind the camera. So, people paid attention when he tried again, this time stepping into the main role as well.

He cast himself as Doug MacRay, who—along with Jeremy Renner’s borderline-psychopath mate Jem—pulls off precision bank heists around their Charlestown patch. Doug's crew might be loyal, but one job turns properly risky when they bag Claire (Rebecca Hall) as a hostage, and Doug can’t shake his conscience. The ever-relentless FBI Special Agent Adam Frawley (Jon Hamm, still mid-Mad Men celebrity at the time) is right on their tail, ready to make this lot pay for every bank window they’ve ever smashed.

Cast, Chemistry, and One Brilliant Line

• Ben Affleck as Doug MacRay—your complex, not-quite-redeemable lead.
• Jeremy Renner as Jem Coughlin—the mate who’ll do anything, no questions asked.
• Rebecca Hall as Claire—the hostage who flips Doug’s world.
• Blake Lively and Chris Cooper, both with small but memorable turns that actually pack a punch.
• Titus Welliver and Jon Hamm perfectly cast as the relentless law.

Affleck and Renner are particularly convincing, giving us criminals who actually seem dangerous—none of the pantomime villain nonsense. The mateship between Doug and Jem sits at the heart of the film; Affleck sets it up straight in that now-legendary scene where Doug simply says, 'I need your help. I can't tell you what it is, you can never ask me about it later, and we're gonna hurt some people.' It’s meme-worthy for a reason.

And then there’s Hamm, who makes sure you never forget this is a game of cat and mouse, actually making the FBI agent as entertaining as the criminals. The film wouldn't be the same without those electric exchanges.

Timing couldn’t have been better for this cast, either—Renner had just scored his Oscar nomination for The Hurt Locker, Hall had made a splash in Frost/Nixon and was on the BAFTA radar, while Hamm was still earning fresh Emmy nods thanks to Mad Men. If you want to see people operating at the height of their powers, this was the moment.

What Makes It Stick?

For all its shootouts and set pieces, what actually gives The Town staying power is its focus on relationships and choices. Doug's thing with Claire flips everything, raising the stakes from mere score-settling to something that actually feels tragic. You end up questioning whether loyalty is a strength—or just a life sentence, especially when everyone’s trapped in the same grim cycle. The final line—Doug telling Claire, 'I know I'll see you again — this side or the other'—absolutely nails it. Genuine goosebumps for anyone who likes their endings bittersweet rather than neatly tied up.