"Boston"

1997 · Gus Van Sant · 126 min · Drama

A small film that became a phenomenon, built almost entirely on the strength of its performances and a screenplay that knows exactly when to be funny, when to be raw, and when to shut up and let two actors sit across from each other in a room. Robin Williams turned in career-best dramatic work, Matt Damon announced himself as a serious talent, and the script they all believed in earned every bit of its commercial and critical success. It follows a familiar path and wraps things up a little too cleanly, but the emotional core hits so hard that most people don't care. Nearly three decades later, the therapy scenes alone are enough to justify its reputation.

2006 · Martin Scorsese · 151 min · Crime / Thriller

Martin Scorsese took a Hong Kong crime thriller and rebuilt it as a ferocious, darkly funny Boston epic packed with career-best performances. The ensemble cast is stacked, the dialogue crackles, and the cat-and-mouse tension never lets up across two and a half hours. A forced romantic subplot and some over-the-top moments from Jack Nicholson keep it a half-step below Scorsese's absolute peak. But only a half-step. This is one of the best crime films of its decade, and it holds up on every rewatch.