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Thursday, May 23, 2024

The 20 Most Underrated Movies of the Past 20 Years

Though awards season is already upon us, it certainly doesn’t feel that way. Like so many other things in 2020, Hollywood is in the midst of a sea change. Even if you wanted to, it might be hard to name 10 great films that came out this year off the top of your head. That said, 2020 hasn’t been a total loss for great movies—as long as you know where to look. And if you want to look back even further (as any serious cineaste should), you’ll see that there are lots of movies that you’ve probably overlooked in the past 20 years that are definitely worth revisiting. They’re not all streaming on the major networks, but they can be rented from Amazon, Apple TV+, or YouTube. (We’ve included where you can get those that are streaming below.)

The big question, of course, is: What constitutes a movie being “underrated”? For the purposes of this list, we looked at movies that tanked at the box office (even if they earned a better reputation once they were available on video-on-demand), films that seemed to invite a number of negative reviews and were worth giving a second chance, and movies that were well-reviewed by both critics and viewers, but just never seemed to find an audience. With that in mind, here's everything you need to catch up on before starting your next 20 years of watching movies. 

The Assistant

Ozark star Julia Garner delivers a brilliantly subtle performance as Jane, a recently hired assistant to a major Hollywood power player. While the bulk of her day involves monotonous tasks like answering phones and replenishing the refrigerator’s water supply, it’s within these mundanities that Jane—and the audience—begin to notice small details around the office that hint that not everything going on behind closed doors is appropriate. Garner’s performance, coupled with the film’s understated approach to the film industry’s rampant objectification and outright abuse of women, are what make The Assistant so effective. Writer/director Kitty Green (Casting JonBenét) trusts her audience to read between the lines and understand that this is a timely take on the Harvey Weinsteins of Hollywood. While The Assistant received great reviews nearly across the board, the film didn’t get much of a theatrical release (and made just $1 million). Hopefully that can change now that it’s streaming.

Where to stream it: Hulu


Lena (Natalie Portman) is a cellular biologist whose Green Beret husband Kane (Oscar Isaac) suddenly shows up at home a year after being dispatched by the government to analyze an anomalous zone deemed “The Shimmer.” Kane has no recollection of where he has been, or how he got back. As his condition deteriorates, Lena is called out on a mission of her own to go explore The Shimmer herself. But when she and her team arrive, strange things start to happen—and it becomes clear that not everyone will make it out alive. While Annihilation was fairly well received by critics, it was pretty polarizing among audiences, and it’s almost easy to see why. The film was written and directed by Alex Garland, the man behind Ex-Machina (2014) and this year’s FX miniseries Devs—both projects that mix sci-fi themes with deep philosophical questions. Annihilation is no different, and will have you thinking about life, death, and the nature of humanity itself for days after. 

Where to stream it: Amazon, YouTube

Good Time

Robert Pattinson never seemed comfortable as the vampire teen idol the Twilight series turned him into, and he’s made very smart decisions in the wake of that franchise to establish himself as one of cinema’s most interesting actors. Good Time is one of the movies that helped put him in this enviable position, as it marked a turning point in Pattinson’s career and helped further establish the Safdie brothers as two of the most compelling directors working today. There’s a visceral feeling with all their work—you can feel your heartbeat quickening with each new scene. In the case of Good Time, Pattinson plays Connie Nikas, a bank robber who recruits his developmentally disabled brother Nick (codirector Benny Safdie) to help him in his criminal endeavors. But Connie might not be as slick as he thinks, and when the two brothers get arrested, Connie then spends the rest of the film trying to bust Nick out of the hospital he’s been placed in—without stopping to think what might be best for his brother. Like 2019’s Uncut Gems, Good Time is made in such a way that you can almost feel the walls closing in on you—which is a good thing.

Where to stream it: Netflix

99 Homes

After stops at some of the world’s biggest festivals, including Venice (where it won Best Film), Telluride, Toronto, and Sundance, 99 Homes had a rather limited theatrical release that brought in less than $1.5 million. Which is surprising, given its major cast—Andrew Garfield, Laura Dern, and Michael Shannon, who earned both Golden Globe and SAG Award nominations for the role of callous real estate pro Rick Carver who thrives in the midst of an economic dip by evicting homeowners with no regard for their individual situations. Dennis Nash (Andrew Garfield) is one of those evictees, who is working as hard as he can to keep a roof over his family’s head, including his mother’s (played by Laura Dern). When Carver offers Nash a job doing the evictions for him, the money is too good to pass up, so he reluctantly agrees—and quickly comes to regret it. The film’s powerhouse cast is as great as you’d expect them do be, with Shannon specifically playing the role of unhinged megalomaniac to utter perfection.

Where to stream it: Tubi

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The One I Love

One has to imagine that confusing marketing was one of the reasons Charlie McDowell’s The One I Love didn’t take off at the box office. Though it was marketed as a romantic comedy, the film falls more heavily into sci-fi territory. Mark Duplass and Elisabeth Moss star as a couple having trouble in their relationship, and seeing a therapist to help head off their problems. When the good doctor (Ted Danson) offers them a lovely, secluded place to stay, weird things start happening. Tonally, the film takes a lot of detours and what sort of starts out as a rom-com eventually morphs into full-on “weird” territory. But it’s a journey worth taking—especially if you like unpredictability in your cinema.

Where to stream it: Netflix


Tell someone you want to spend 85 minutes watching a movie about a man driving in his car and talking on his cell phone the entire time and you’ll likely get a series of giant eyerolls. But then tell the same person that the man driving the car is Tom Hardy, and see if their opinion changes. While Hardy’s face is the only one we see (again, this truly is a movie that features a man driving a car for an hour and a half), he’s surrounded by a bevy of voice talent, including Ruth Wilson as his wife, Tom Holland as his son, Olivia Colman as his ex-mistress (who is pregnant), and Andrew Scott (aka The Hot Priest) as a co-worker desperate to get Hardy’s Ivan Locke to attend to his professional business, not his private matters.

Where to stream it: Showtime, Amazon, YouTube


There’s no point in sugar-coating the fact that Enemy is, well, strange. But tonal shifts and last-minute twists are something audiences have come to expect from Denis Villeneuve (Prisoners, Arrival). In the case of Enemy, the less you know about the movie going in the more likely you are to enjoy it. Jake Gyllenhaal stars as a quiet college professor who discovers he has a doppelgänger. Intrigued, and confused, he starts following his look-a-like to see what he’s up to, and why their lives seem to keep intersecting. It’s not likely that the ending is something anyone would predict.

Where to stream it: Showtime, YouTube

Seeking a Friend for the End of the World

Keira Knightley sheds the elaborate period clothing so many directors want to put her in and joins the modern world in this apocalyptic rom-com. When it’s announced that the world will end in three weeks, people act in all sorts of weird ways. For married couple Linda and Dodge (Nancy Carell and Steve Carell), it means Linda running off in a panic and calling an immediate end to their marriage. For Dodge, business as usual seems to be the best way to deal with the end of the world, so he continues going into work and living out his last days as he always has. But when he befriends Penny (Keira Knightley), his young and seemingly impulsive neighbor, they both realize there’s something left for them to do: for Penny, it’s seeing her family one last time. In Dodge’s case, it’s finding the woman he once loved—“the one that got away”—and spending his final days with her. So the two embark on a road trip, which allows them to see how the rest of the world is reacting to the fatal news and to discover who they really are when there’s no reason to not be completely honest.

Where to stream it: Peacock

We Need to Talk About Kevin

If you’re looking for a feel-good movie … this is not it! That said, it’s a fascinating—albeit depressing—watch. Eva Khatchadourian (Tilda Swinton) and Franklin Plaskett (John C. Reilly) are parents to a teenager named Kevin (Ezra Miller) who has committed a horrible act of violence at school. In the wake of the tragedy, Eva flashes back on her life with Kevin, and how she has always felt that there was something evil about him. If you want to feel better about your own family dysfunction, We Need to Talk About Kevin will definitely do the trick.

Where to stream it: Hulu, Amazon


Dr. Catherine Stewart (Julianne Moore) and her husband David (Liam Neeson) have been married for several years and Catherine begins to suspect that David, a college professor, might be having an affair with his student. To discover more, she hires a call girl named Chloe (Amanda Seyfried) to flirt with David then report back to her. As Chloe indulges Catherine’s request to tell every last detail of her affair with David, some lines get crossed. Neeson, Moore, and Seyfried all play against type in this sexual-thriller that mixes B-movie tropes with a Fatal Attraction-like storyline, but manages to do it in an intelligent way thanks to director Atom Egoyan, who might just be one of the all-time most underrated directors, especially when it comes to ‘90s output like Exotica and The Sweet Hereafter).

Where to stream it: Hulu, Starz

Big Fan

Paul Aufiero (Patton Oswalt) doesn’t have a lot going on in life. By day, he works as a parking garage attendant and still lives at home with his mom in Staten Island. At night, he calls into his favorite sports radio talk show, where he’s a regular caller known as “Paul from Staten Island.” It’s here, within the sports world, that Paul feels like he can be his own man and create an identity for himself. But his fandom is put to the test when he and his best friend spot one of the team’s major players and follow him around for a while. When Paul finally gets up the nerve to approach his hero, things don’t go as well as expected. In fact, they don’t go well at all and Paul is left to make a choice between fandom and fairness. Oswalt is perfect in the role, which allows him to show off his dramatic side (which you may not have known even existed).

Where to stream it: Tubi, Peacock

The Strangers

The main complaint critics and audiences had with Bryan Bertino’s horror flick is that there wasn’t enough character development or plot. But when a group of mask-faced killers are poking around your house trying to kill you, see if any of that really matters. To be honest, the fact that the murderers choose to terrorize Liv Tyler and Scott Speedman simply because “they were home” really only ups the creep factor.

Where to stream it: Amazon

The Foot Fist Way

It took a couple of years for The Foot Fist Way to finally make it into theaters, and even that was largely courtesy of Will Ferrell and Adam McKay seeing it and releasing it through their Gary Sanchez Productions. But even after all that, plus screenings at Sundance and the Los Angeles Film Festival, it still earned less than $250,000 when it was released. It’s easy to imagine that things could have been different if Danny McBride had been a better-known entity at the time. After all, anyone who loves Kenny Powers would surely adore McBride’s Fred Simmons, yet another obnoxious small-town hero—in this case a Tae Kwon Do teacher—who plans a road trip for a couple of his closest friends and students to go watch Simmons’ idol, Chuck "The Truck" Wallace, fight at a seminar.

Where to stream it: CBS All Access, Pluto TV

The Fountain

We’re not going to lie: There’s a hell of a lot to unpack in The Fountain, Darren Aronofsky’s passion project. While there’s some truth to the criticisms that the movie is a bit too big and navel-gazing for its own good, there’s also a lot to like about it if you give it the time and attention it deserves (stop scrolling Twitter). The film is packed with time travel and philosophical conversations and situations surrounding love, death, and immortality. Hugh Jackman stars as the man on a quest for love and eternal life, which plays out in several different times and places. To say much more than that would be to go too deep into the story and give too much away. Is The Fountain too ambitious? Probably. But it’s a lot more interesting than most of what comes out. Plus: It’s only 96 minutes long, so what have you got to lose?

Where to stream it: HBO Max, Hulu

Perfume: The Story of a Murderer

Whether you know it or not, Ben Whishaw is one of the greatest actors of his generation. (Yes, this is a fact.) Fresh off his triumphant run in the Olivier Award-nominated title role of Hamlet at the Old Vic, Whishaw took on the starring role in this adaptation of Patrick Süskind’s 1985 novel. It follows the life of Jean-Baptiste Grenouille (Whishaw)—from his abandonment as an infant to his sentencing in court with his life as a murderer in between. Grenouille has an obsession with the scent of things, a talent that leads him to becoming one of Paris’s most famous perfumers. But his obsession with smells, and recreating them, leads him down some dark paths that, once traveled, cannot be undone.

Where to stream it: Pluto TV, Amazon

Two for the Money

A few years before the McConaissance kicked into high gear, Matthew McConaughey teamed up with Al Pacino for this sports crime drama that is harmless fun. McConaughey plays Brandon Lang, a former college sports star who hooks up with Walter Abrams, a sports consultant who takes Lang under his wing to teach him the rules of handicapping. Together, the two work with high-rolling clients to help make and pick bets. But like any kind of winning streak, their good luck is bound to come to an end, which is when the real drama sets in.

Where to stream it: Hulu

The Assassination of Richard Nixon

Sean Penn stars as Sam Bicke—a down-on-his-luck salesman who determines that the best way to turn his life around is to hijack a plane and crash it into the White House (where Richard Nixon resides). After going on a mini-rampage in his hometown of Philadelphia, Bicke attempts to board a plane for Washington, DC with a gun and a suitcase full of gasoline. But as with everything else in Bicke’s life, the hijack does not go off as planned. The film is based on the true story of Samuel Byck.

Where to stream it: N/A

Owning Mahowny

Dan Mahowny (Philip Seymour Hoffman) is an assistant bank manager who has a job he likes, a girlfriend who loves him, and a debilitating gambling addiction. So when he sees a way that he can leverage the money that’s coming into the bank to help him rack up bigger dollar totals at the casino, it seems like a no-brainer. While he initially finds some success with this scheme, it doesn’t last long. And by the time he’s finished, he now owes his employer a lot of money—and needs to get it back to them soon. Though the film only made back about $1 million of its $10 million budget, Roger Ebert called Owning Mahowny one of the top 10 films of 2003, and specifically cited Hoffman’s performance, stating that it was "a masterpiece of discipline and precision" and described Hoffman as a "fearless poet of implosion, [who] plays the role with a fierce integrity, never sending out signals for our sympathy because he knows that Mahowny is oblivious to our presence."

Where to stream it: N/A

The Believer

Years before Ryan Gosling was “OMG—Ryan Gosling!” the then-21-year-old took on a role that would intimidate most actors his age (and many actors twice his age) when he played Danny Blint, a Jewish yeshiva student-turned-neo-Nazi in The Believer. Jamie Russell of BBC Films described the film as "awe-inspiring … a late contender for one of the best films of the year—an intellectually breathtaking, profoundly moving film." But due to protests and the wake of 9/11, theaters ultimately decided not to book the film and we never heard much about it.

Where to stream it: Amazon

Vanilla Sky

David Aames (Tom Cruise) has got it all: looks, wealth, great friends. Just when he thinks his life can’t get any better, his best friend (Jason Lee) introduces him to a woman named Sofia (Penélope Cruz) and the two of them fall in love. While David is ecstatic, his “fuck buddy” (Cameron Diaz) isn’t so thrilled. So she takes David on a car ride that she hopes will end both their lives. Instead, it leaves David with a severely damaged face that can’t be repaired by plastic surgery, so he opts to wear a creepy mask around instead. And that’s when things get really bizarre. Though it made over $100 million at the box office, Vanilla Sky got killed by critics—many of whom wondered why Cameron Crowe would exhaust so much time and energy remaking what was already a great film (Alejandro Amenábar's 1997 Spanish film, Open Your Eyes). Others seemed to think that the movie was simply an exercise in vapidity (which was sort of the point, but we’ll leave that to one side for now).

Where to stream it: Pluto TV, CBS All Access

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