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5. Shutter Island (2010) This pulpy thriller is easily one of Scorsese's purest expressions, and it's also the best film of his current period. Less self-serious than The Departed and less sentimental than Hugo, it features his trademark use of expressionistic color (the kind that would make Michael Powell proud), interwoven narratives, and subtle experimentation with continuity editing. The film, though aesthetically rigorous, is effortlessly entertaining, and Scorsese displays the exuberance of a filmmaker half his age.
4. Taxi Driver (1976) Pulling out all the stops, Scorsese directed this film like he'd never have the chance to direct another film again. Similar to Spielberg's Jaws and Coppola's Apocalypse Now, the film is indicative of a director at the height of some sort of manic spree, featuring everything from a vividly detailed milieu, ephemeral or otherwise surrealistic characterization, and overall stylistic conviction. He's rarely exhibited such bravado since.
3. My Voyage to Italy (1999) As I noted above, Scorsese is as valuable a film lover as he is a filmmaker. (Look no further than the Film Foundation for proof.) This four-hour-long TV documentary details his infatuation with Italian cinema, and while it may not illuminate any new or particularly revolutionary information on the subject, Scorsese's knowledge and exuberance is infectious. That said, he does provide some insightful comments on the great Roberto Rossellini, whose influence can be found in virtually every Scorsese film.
2. Casino (1995) Too often regarded as a poor man's Goodfellas, Casino is Scorsese's most novelistic work. As he's proven on multiple occasions, Scorsese is a true American mythmaker. Casino, with its examination of capitalist structures, enterprising (in other words, selfish) characters, and ambitious if somewhat defeatist use of historical context, this complex survey of big crime clashing with big business is the closest Scorsese has gotten to a magnum opus.
1. The King of Comedy (1983) The sillier but no less unsettling B side to Taxi Driver, this dark comedy failed to resonate with audiences upon initial release, but it's since risen in stature. I disagree with Dave Kehr when he writes, "Scorsese is trying to distance himself from his characters . . . he finds them grotesque." To me, Scorsese seems quite taken with his cast of miscreants (particularly Juliette Lewis, who's in pure batshit mode), whereas elements of the grotesque seem to exist externally. In other words, it's the era (early Reagan America) and the milieu (materialist New York City) he finds grotesque. In truth, the characters are ultimately some of his most sympathetic, and the movie, however bleak, is subtly one of his most cheerful.