10. Serendipity – Right about the time it seemed John Cusack’s star was fading, he teamed up with Kate Beckinsale for one more run at an absolute charmer of a romantic comedy. The structure of Serendipity, about a very Cusack-ian ESPN producer who chases his love-at-first-sight across the country, only to miss her time and time again, is creative and it makes for a good time. The sticky part of the story involves Cusack’s current girlfriend/fiancé, Halley (Bridget Moynahan), who is a kindhearted person who really doesn’t deserve all this nonsense; but, hey, not scything can be perfect.
What feels like a relic of a different world now has always been light, breezy fun, with some solid supporting performances by Jeremy Piven, Eugene Levy, Molly Shannon, and John Corbett as Lars, a new age, jazzed up version of Kenny G. He’s the real all star.
9. Heist – Somehow, David Mamet’s lean caper thriller starring Gene Hackman didn’t steal audience attention back in 2001. To be fair, there had been a glut of similar movies in the wake of Michael Mann’s Heat (which, amazingly enough, didn’t make big bucks itself in 1995), and the generic title didn’t do it any favors. The story of the aging thief who gets pulled back into one last job will forever be cliche, but this was never a film about plot creativity; it’s al about watching great actors act great.
Heist is a blast, thanks in no small part to Mamet’s rapid-fire, clipped dialogue, and a supporting cast of Danny De Vito, a baby Sam Rockwell, the underrated femme fatale Rebecca Pidgeon, and the rock-solid Delroy Lindo. It’s worth seeking out for any fans of smart, slick crime cinema.
8. A. I. Artificial Intelligence – The idea that Steven Spielberg was going to adapt recently-deceased Stanley Kubrick’s science-fiction Pinocchio fable was one of the strangest and most compelling bits of movie news in 2001. Two wildly different auteurs teaming up, one from beyond the grave, to tell an esoteric, moody sci-fi drama about love and empathy, and what makes us human; it generated great curiosity, anticipation and, ultimately, trepidation.
When the film came out in the summer of ’01, like so many Stanley Kubrick movies, it was met with a side-eyed shrug, or confusion, or disdain. It didn’t work for most people at the time, myself included, but just as every Kubrick story does, it has since evolved into a spellbinding, haunted tale. Haley Joel Osment is incredible as David, the young android boy who is abandoned by his adoptive parents, and must traverse a broken world in search of love, is truly heartbreaking, and Spielberg’s involvement likely rescued the film, preventing it from being too cold and distant to ever get a second chance.
Probably the most impressive thing about the cold reception in 2001 was that Spielberg directed the movie. His films, accessible and crowd-pleasing, were almost always loved right away. The fact that A.I. has taken time to becomes something better than first thought is a testament to Spielberg’s ability to channel the enigmatic Kubrick.
7. Vanilla Sky – After Tom Cruise became the biggest box-office superstar on the planet in the mid ’90s, he spent the end of the decade and the early years of the 21st century trying to shed that matinee idol stardom and break down his lingering aura of The Perfect Human with heavy, vulnerable turns in Eyes Wide Shut and Magnolia and, perhaps the strangest attempt at self deconstruction, Cameron Crowe’s Vanilla Sky.
Easily the strangest, most idiosyncratic major studio release in 2001, Crowe’s remake of Alejandro Amenábar’s 1997 thriller isn’t necessarily a great film by traditional metrics. But it’s fascinating and infinitely entertaining, a story of a man who had everything until his ego got the better of him and upended his life. Only it’s much weirder than that, and should be celebrated for its willingness to eschew conventional storytelling.
6. Ocean’s Eleven – Steven Soderbergh’s effervescent caper remake features, above all else, a remarkable collection of actors hitting cool, comedic notes with a breezy likability that’s since become nonexistent (outside of maybe the Avengers movies). This is Clooney, Pitt, and (on a lesser note) Matt Damon at the height of their powers; it’s the early days of Casey Affleck and Scott Caan; it has legends like Elliot Gould and Carl Reiner; every supporting member of the eleven brings something unique to their role.
The heist itself – cleaning out three casinos belonging to Andy Garcia’s Terry Benedict – is a blast to watch unfold, but the hangout nature of the story is also delightful thanks to the cast. Special shout out to Julia Roberts, who brings a much-needed feminine toughness to this boy’s club, and who turns what could have been a rather thankless role into a crucial counterweight to all that machismo.
5. Sexy Beast – Jonathan Glazer, a music-video director first and foremost, has directed only three films: Under the Skin, Birth, and his first film, Sexy Beast. Each one is brilliant in their own way, and it’s a minor miracle that Glazer not only got Ben Kingsley to appear in his debut feature, but he managed to cultivate the greatest performance of the legendary actor’s career.
Kingsley is Don Logan, a towering psychopath, a man who send chills up the spine of our hero, Gal, a happily retired and sunbaked thief played by Ray Winstone. Don Logan is on his way to talk Gal into one last job, and his presence t the Spanish villa upsets everything and everyone. Sexy Beast is a ferocious thriller, hard charging and buzzing with an electronic, pulsating score, and a performance from Ben Kingsley that is unlike anything you’ve ever seen.
4. Training Day – Despite the fact Denzel Washington won Best Actor for playing wicked street cop Alonzo Harris, and Ethan Hawke was nominated for playing Jake, his parter (and, ultimately, the scapegoat for a heist), Training Day still felt like a well-made but thin genre exercise. Like so many of the films on this list, however, time and multiple revisits have only enriched Antoine Fuqua’s picture; it’s kind of a masterpiece.
The machinations of the plot are overshadowed by Washington’s volcanic performance the first time you see the film. Once you are familiar with the rhythms of performance, however, the elaborate ruse of the story begins to shine. This film is put together like a Swiss watch, with plenty of genre flourishes and bombastic dialogue to excite an action fans. It’s easy to lose sight of what makes the film so brilliant from top to bottom when seen only through memory flashes of big Washington speeches, King Kong, etc… but there is so much more at play here.
3. Mulholland Drive – My love/hate relationship with David Lynch is one of the most frustrating mental blocks in my personal cinematic sentience. I try and try again to engage with his more esoteric works, like Lost Highway, Wild at Heart, and with Mulholland Drive. Despite the fact I can’t quite sync up with the auteurs hyper specific style and dream logic in his later films (nobody will ever be able to convince me Inland Empire was made with the intention of ever actually being seen by humans), it’s easy to recognize the brilliance of Mulholland Drive.
It’s the peak of Lynch’s detached, nightmare logic cinema. It makes sense for a while, until it doesn’t, but set against the backdrop of Hollywood, there’s more truth in the disorienting nature of the story than there would be against any other setting. It can be frustrating for anyone who needs resolution, but if you can learn to stop worrying and love the nightmare, Mulholland Drive manages to curate all the beautiful madness of Lynch’s brain into one hypnotic masterpiece.
2. The Royal Tenenbaums – Much like Lynch, Wes Anderson is someone with whom I cannot engage like it seems everyone else can. Unlike Lynch, however, there is very little guilt associated with this feeling; if you ask me, Wes Anderson has become a slave to his own style, an annoying twee filmmaker whose stories are lost amid the cutesy nature of his productions. But, in 2001, that very twee-ness manages to hit all the right notes at the right time, with the right cast.
Gene Hackman is exceptional as the despicable – but somehow still lovable – patriarch of a family of geniuses who never reached their respective potentials. All of the elements that make Anderson’s film insufferable today are perfectly placed, from the manicured sets, the hyper-specific wardrobes, the soundtrack, and the comedic timing. Hackman deserved an Oscar nomination for his performance, and Anderson should stop trying to recreate the magic he found with this, his best film.
1. In the Bedroom – Sometimes, great films can also be horribly depressing, so much so that they’re often labeled by many as “a great movie I’ll never watch again.” That’s fair sometimes, but to deny yourself repeat viewings of In the Bedroom is to deny yourself the opportunity to see great actors doing the best work of their careers.
Todd Field’s story of tragedy, grief, and revenge, is a tale of two parents dealing with the murder of their son in different ways. So different, in fact, that it almost tears them apart. Sissy Spacek is simmering rage, Tom Wilkinson is desperate suppression, and when their emotions finally explode in the presence of one another, it is one of the most powerful and honest scenes you will ever see. Marisa Tomei, as the woman caught in the middle of this family tragedy, shows exactly why she is one of the most underrated, compelling actresses of her generation.
It may be a hard watch, too hard for some, but occasionally we might need to see the darkness to find our own light.