Summary

• Martin Scorsese's movies span a wide range of themes, styles, and genres, showcasing his often-overlooked versatility as a director.
• While he has never made a truly terrible film, some of his early works like "Boxcar Bertha" and "New York, New York" demonstrate a director still finding his footing.
• Collaborations with Leonardo DiCaprio, such as "Shutter Island," have yielded commercial success, but may lack the emotional depth and personal touch of Scorsese's best works.

Martin Scorsese's many Oscar nominations, his influence over Hollywood cannot be overstated.

The longevity of his directing career has put him in the fascinating position of never having made a truly terrible film, something that few of his contemporaries, such as Spielberg and Francis Ford Coppola, can claim for themselves. With over 25 features (which does not include any of his documentaries), Scorsese has shown his oft-overlooked range in theme, style, and genre, moving gracefully from the stylistic bombast of the gangster movie to the quiet dignity of period drama. That continued experimental nature of the auteur means ranking Martin Scorsese's movies becomes quite the challenge with each new potential masterpiece.

26 Boxcar Bertha

Gene Siskel famously referred to Boxcar Bertha, Scorsese's second film, as a "trashy movie" that "does not shock [but] merely depresses." He's not wrong: It is pretty trashy, but it's also somewhat expected from the pairing of 28-year-old Scorsese with legendary B-movie titan Roger Corman. Scorsese's clearly having a lot of fun with this vague Bonnie and Clyde rip-off, but it's also a director still working with the training wheels on. He had yet to iron out the creases and take on these themes with the level of skill and ambition that becomes clear later on in his work.

25 The Color of Money

In 1986, it was something of a surprise to see Scorsese of all people directing a sequel, much less one for a film he didn't even make himself. Still, The Color of Money is perfectly entertaining as Tom Cruise and Paul Newman made an endlessly charismatic duo, but it's also clear that Scorsese's personal touch is light from this project. The film mostly existed as a way for Newman to finally win his Best Actor Oscar after decades of snubs, and fortunately, it did just that. This is Scorsese more as a hired studio hand than an auteur, which puts it further back in ranking the legendary director's filmography.

24 New York, New York

New York, New York was a curious choice for Scorsese, and it's clear that his ambitions got the better of him. Robert De Niro plays a small-time saxophone player who falls for a USO singer (Liza Minnelli). Their relationship is messy, obsessive, and often deeply creative. It's obvious that Scorsese has a deep love for the musicals of classic Hollywood and there are moments of real old-school razzle-dazzle, especially when Minnelli belts those Kander and Ebb songs. Peter Biskind's book Easy Riders, Raging Bulls claims that Scorsese's cocaine addiction and difficulties in dealing with the often improvised dialogue were what sank the film outside a few brief magical moments.

23 Who’s That Knocking at My Door?

Filmed over the course of several years, Who's That Knocking at My Door was Scorsese's cinematic debut, originally starting life as a student short film. From the beginning, many of his favored themes as a storyteller are present, including the Catholic Italian-American male experience in New York City. Harvey Keitel plays J.R., a young man floating through life who then falls for a beautiful girl with a terrible secret. As it stands, Who's That Knocking at My Door is not the greatest directorial debut in American cinema, but it's still a top-notch calling card for a talented guy with a bright future ahead of him.

22 Shutter Island

For much of the 21st century, Scorsese’s most prominent collaborator has been Leonardo DiCaprio. Their movies together have given the director some of his highest-grossing works as well as a new partnership to rival that of the one he has with Robert De Niro. Shutter Island is the weakest of the Martin Scorsese and Leonardo DiCaprio movies, although it is not without immense ambition and memorable chills. Based on a book by Dennis Lehane, Shutter Island features an enviable all-star cast that includes DiCaprio, Mark Ruffalo, Max von Sydow, Michelle Williams, and Jackie Earle Haley.

This mind-twisting story of a traumatized U.S. Marshal called into a hospital for the criminally insane to investigate a missing patient has some truly terrifying moments. The ultimate reveal in Shutter Island's ending still holds up years later, and it is undoubtedly fun to see Scorsese bring his talents to a horror-thriller like this. But, the movie is also emotionally distant in a way Scorsese typically avoids. This is the director throwing everything at the wall to see what sticks to mixed results.

21 Hugo

Many of Scorsese’s films act as love letters to the history of cinema and nowhere is that more evident than in Hugo, his first real array into family-friendly entertainment. Kids may not have been as dazzled by this immersive journey into the world of pioneering filmmaker Georges Méliès, but Hugo is Scorsese at his most heart-warming and earnest. There are scenes where he goes full-on Spielberg with the emotions! Alas, what makes the film stumble is Scorsese seems to occasionally forget it was supposed to be, first and foremost, a kids’ film and he allows himself to be a tad overindulgent with his Méliès fandom.

20 The Aviator

For many months in 2004, Hollywood was convinced The Aviator, Scorsese’s biopic of Howard Hughes, would be the one that finally cinched him that long-sought-after Best Director Oscar. It’s not hard to see why The Aviator attracted such attention. It’s easily one of his most conventional movies and the one that seemed tailor-made for a particular brand of middle-of-the-road industry prestige. Fortunately, the story gives Scorsese plenty of opportunity to show off his rich array of skills, all while showing off in the playground of old Hollywood.

Hughes is a perfect match for Scorsese, a deeply difficult but brilliant figure whose hubris and demons quickly got the better of him. The Aviator is at its best when, as the title suggests, Scorsese lets rip with the astounding flying scenes. The scene where Hughes crashes his plane through Beverly Hills during a test flight gone wrong may be one of the best set pieces Scorsese has ever executed.

19 Gangs of New York

It’s always better to have too much ambition than not enough, and the best exemplification of that as it pertains to Scorsese is Gangs of New York. The film famously went through some tough behind-the-scenes drama that involved producer Harvey Weinstein cutting an hour from its running time and delaying its release a whole year. Weinstein’s fingerprints are depressingly evident throughout the film, most obviously in the painful miscasting of Cameron Diaz; Scorsese wanted the less bankable but more fitting Sarah Polley for the part.

Still, Gangs of New York is the perfect subject for Scorsese: The battles on the streets of a newly evolving city, involving Catholic-Protestant feuds, Irish immigrant protests, and the gangs of Manhattan's Five Points. For as messy and often exhausting as the film is, its grandeur and meticulous attention to historical detail make it worth your time. Daniel Day-Lewis is electrifying as William "Bill the Butcher" Cutting, although many of the strong cast struggle with those Irish accents. For all its faults, Gangs of New York's ending may be one of the truly perfect moments in Scorsese's career.

18 After Hours

After Hours sees Griffin Dunne star as a mundane office worker who experiences the night from hell that includes burglars played by Cheech and Chong, a gang of punks, bagel paperweights, and a dead woman. This deeply and darkly funny comedy features a murderer's row of sinfully underrated actors, including Catherine O'Hara. There’s a wonderful rough edge to After Hours that feels like the work of a much younger and freer director. Although it won Scorsese Best Director at Cannes, After Hours received mixed reviews upon its release. It took a few years for people to rightfully appreciate it as one of the hidden gems in his filmography.

17 Cape Fear

Scorsese is capable of having the lightest of touches but now and then it's oh-so-satisfying to see him take the restraints off. He does that and then some with his 1991 remake of Cape Fear. He and De Niro giddily embrace their showiest aspects and amp up the tension of the original narrative to new heights. Moreover, Scorsese made a wise but very precarious decision to increase the disturbing undertones of the original, especially in the subplot involving Juliette Lewis. Cape Fear is kind of disgusting but in the best way possible, as Scorsese pushes the right buttons so the moments of true perversity in Cape Fear still shock.