Amazon Prime Video isn’t slacking off when it comes to adding new movies this month. We already ranked Prime Video as one of the best streaming services, and its consistently stellar lineup of movies is a big part of the reason why — and May is continuing that trend.
In fact, this month Prime Video just got one of my favorite movies of the year so far. And it stars two Hollywood heavyweights in Ben Affleck and Matt Damon, and Affleck even stepped behind the camera for this one serving as the director as well.
Prime Video’s May lineup also includes modern classics from legendary directors Martin Scorsese and Wes Anderson. Plus, there’s a movie on this list where you get to see Jason Segel’s bare butt! I’m not sure if that’s actually a selling point, but it happens in the movie multiple times.
All of these movies could make a strong case for inclusion in our roundup of the best movies on Prime Video, so if you’re looking for something new to watch on Amazon’s streaming service this month, here are my top seven recommendations.
Air (2023)
Air joins the likes of The Social Network and Moneyball on the list of movies that sound conceptually dull but turn out to be extremely enjoyable. Released in theatres last month, this Ben Affleck-directed sports drama is already a shoe-in to be among the year’s best movies.
The easy-going flick tells the true story of Nike’s attempts to woo up-and-coming basketball player Michael Jordan in an effort to convince him to sign a contract with them over sportswear rival Adidas. On paper that doesn’t exactly sound like the most compelling hook for a film, but watching Nike exec Sonny Vaccaro (Matt Damon) scramble as he attempts to put together a presentation for the athletics no-nonsense mother (the ever-excellent Viola Davis) is highly engaging.
Sonny also has to persuade his reluctant boss, Phil Knight (Affleck), and colleague Rob Strasser (Jason Bateman), that Jordan is worth the effort and financial commitment. Of course, the resulting partnership would birth one of the most iconic sneakers in history, the Air Jordan, and the movie does a great job showcasing its origins.
Genre: Sports drama
Rotten Tomatoes: 92%
Stars: Matt Damon, Ben Affleck, Jason Bateman, Viola Davis, Marlon Wayans, Chris Tucker
Director: Ben Affleck
Stream it on Prime Video
A Beautiful Mind (2001)
Sweeping the 74th annual Oscars, A Beautiful Mind scooped up Best Picture, Best Director, Best Adapted and Best Supporting Actor with further nominations in four more categories including Best Actor for Russell Crowe’s leading turn as celebrated mathematician John Nash.
Inspired by Sylvia Nasar’s biography of the same name, A Beautiful Mind opens with the brilliant but socially awkward Nash arriving at Princeton University in 1947. Flash forward a few years and Nash’s brilliance is noticed by the Pentagon who enlist his help studying encrypted telecommunications, but as his obsession over this top-secret assignment grows he becomes convinced that he is being watched and that sinister forces may be following him.
Crowe is far from the only standout in the movie's impressive cast list, Ed Harris, Jennifer Connelly and Paul Bettany are also excellent, and there’s a role for Christopher Plummer as well as a psychiatrist named Dr. Rosen who attempts to help Nash manage his troubled psyche. On the surface, A Beautiful Mind may look like disposable Oscar bait but it’s so much richer.
Genre: Drama
Rotten Tomatoes: 74%
Stars: Russell Crowe, Ed Harris, Jennifer Connelly, Paul Bettany, Adam Goldberg, Christopher Plummer
Director: Ron Howard
Stream it on Prime Video
She Said (2022)
Based on the book of the same name, She Said recounts the New York Times investigation that exposed decades of sexual abuse and misconduct by famed Hollywood product Harvey Weinstein.
The film is centered around two dogmatic journalists, Jodi Kantor (Carey Mulligan) and Megan Twohey (Zoe Kazan), who worked tirelessly to expose Weinstein’s crimes and ensure that the women he took advantage of are given a platform to speak their truth. It's all very powerful stuff, and it’s a salient and well-timed reminder that we must listen to and believe victims of sexual abuse when they speak up.
Mulligan and Kazan anchor the film expertly, and director Maria Schrader does a marvelous job making quote-gathering phone calls feel as tense as any blockbuster action scene. Plus, credit must go to Mike Houston for playing the difficult role of Weinstein. Certainly not the most fun watch on this list, She Said is nevertheless powerful cinema that should be watched by all.
Genre: Drama
Rotten Tomatoes: 88%
Stars: Carey Mulligan, Zoe Kazan, Patricia Clarkson, Andre Braugher, Jennifer Ehle, Ashley Judd
Director: Maria Schrader
Stream it on Prime Video
Bill & Ted’s Excellent Adventure (1989)
Forget John Wick or Neo, Keanu Reeve's best character ever is Ted Logan, a dim-witted high school student who, along with his best friend Bill (Alex Winter), uses a phone booth-shaped time machine to travel back to the past and assemble a crew of historical figures for a history class presentation.
This madcap sci-fi comedy blends absurdist humor with a pair of seriously likable lead characters. The movie more than lives up to its name offering a genuinely excellent adventure that sees the duo meet all sorts of famous figures including Napoleon Bonaparte, Joan of Arc, Abraham Lincoln and even Socrates.
The movie is pretty much as silly as it sounds, but it’s very earnest and pleasingly self-aware. A similarly fun sequel would follow two years later, 1991’s Bill & Ted’s Bogus Journey, and this was followed by a long-anticipated third movie released in 2020, Bill & Ted Face the Music, which didn’t quite hit the heights of the most excellent original.
Genre: Comedy
Rotten Tomatoes: 82%
Stars: Keanu Reeves, Alex Winter, Robert V. Barron, Terry Camilleri, Clifford David, Jane Wiedlin
Director: Stephen Herek
Stream it on Prime Video
Forgetting Sarah Marshall (2008)
One of the most consistently funny comedy films of the 2000s, Forgetting Sarah Marshall sees Jason Segel play Peter Bretter, a composer for a popular crime drama show that stars the titular Sarah Marshall (Kristen Bell). Oh, and Peter’s also been dating Sarah for five years, and she just dumped him to date a British Rockstar (Russell Brand) instead.
Flying to Hawaii in an effort to escape his heartbreak, Peter winds up at the same resort that Sarah is staying at with her new rocker beau. It’s a situation ripe for comedy, and the film gets great mileage out of some truly toe-curlingly uncomfortable situations. Alongside the excellent leads is a top-class supporting cast of very funny people including Mila Kunis, Bill Hader, Jonah Hill, Jack McBrayer and Paul Rudd.
Forgetting Sarah Marshall is a movie that I still quote regularly to this day, more than a decade on from my first viewing, which is a testament to its seriously funny writing. Plus, it’s the only movie on this list that features a Dracula musical with puppets, which should be enough for it to earn a spot in your Prime Video watchlist.
Genre: Comedy
Rotten Tomatoes: 83%
Stars: Jason Segel, Kristen Bell, Mila Kunis, Russell Brand, Jonah Hill, Paul Rudd, Bill Hader
Director: Nicholas Stoller
Stream it on Prime Video
Shutter Island (2010)
Standing out in a filmography as impressive as Martin Scorsese’s is a difficult task but Shutter Island manages to rank as one of the iconic director’s most thrilling movies because of its nerve-shredding tension and expertly plotted mystery.
Set in 1954, Shutter Island follows a U.S. Marshall named Teddy Daniels (Leonardo DiCaprio) who arrives with his partner Chuck (Mark Ruffalo) at an institute for the criminally insane on the eponymous island. Their job is to investigate the strange disappearance of a patient in the middle of the night, but the duo soon starts to suspect that everything is not what it seems on Shutter Island and that the enigmatic psychiatrist Dr. John Cawley (Ben Kingsley) may be hiding dark secrets.
A twisting tale that will leave you guessing until the very end Shutter Island is the sort of movie that is more enjoyable the less you know before watching, so for fear of spoilers I’ll say no more other than it’s an essential watch for thriller fans.
Genre: Thriller
Rotten Tomatoes: 68%
Stars: Leonardo DiCaprio, Mark Ruffalo, Ben Kingsley, Michelle Williams, Emily Mortimer, Patricia Clarkson
Director: Martin Scorsese
Stream it on Prime Video
Moonrise Kingdom (2012)
A quintessentially Wes Anderson movie, Moonrise Kingdom is set on the fictional island of New Penzance and sees a young boy escape his scouting trope in order to unite with his pen pal, a young girl with aggressive tendencies. In response, the island’s police captain organizes a search party to look for the runaways and the island’s colorful inhabitants pitch in to help with the search.
As you might expect from a Wes Anderson flick, Moonrise Kingdom packs a stellar cast with several of the director’s preferred collaborates in the mix. Here you’ll find excellent performances from Bruce Willis, Edward Norton, Bill Murray, Frances McDormand, Tilda Swinton and, of course, Jason Schwartzman. The first feature film performances from Jared Gilman and Kara Hayward as the two runaway kids shouldn’t be overlooked either.
Anderson’s latest movie, Asteroid City, is scheduled to hit theatres next month so now is the perfect time to revisit one of his best efforts to date. Inspired by his own childhood fantasies, Moonrise Kingdom is a unique filmmaker at the peak of his powers.
Genre: Comedy
Rotten Tomatoes: 93%
Stars: Bruce Willis, Edward Norton, Bill Murray, Frances McDormand, Tilda Swinton, Jason Schwartzman
Director: Wes Anderson
Stream it on Prime Video
