The 15 best films on Prime Video for May 2023

Paul Thomas Anderson is one of our greatest living filmmakers. And while Boogie Nights is fairly unassailable, his first foray into feature filmmaking was the scrappy 1996 starring Philip Baker Hall, John C. Reilly, and then-indie “it girl,” Gwyneth Paltrow. Based on Coffee & Cigarettes, a very early Anderson short film, Hard Eight follows lovable loser John Finnegan (Reilly) who befriends a gambler named Sydney who, as the film progresses, is gambling with a lot more than money.

Based on the true story of Mamie Till-Mobley’s pursuit of justice for her murdered 14-year-old son, Emmett Till, many thought 2022's  was unfairly shut out of the Oscar race. While this may very well be true, the film also stumbled a bit in terms of reaching an audience which, for a smaller film, can often spell disaster for awards season contenders. Here’s hoping the Prime Video platform finds a wider audience for Chinonye Chukwu’s film, which stars Danielle Deadwiler as Till-Mobley and Jalyn Hall as her son.

Has anyone ever floated the idea that director John Ford’s muse was John Wayne? Just asking. The director and actor created some of the greatest Westerns of all time, including Stagecoach, The Searchers, and The Man Who Shot Liberty Valance. But in 1952 the duo mixed it up with , the tale of an Irish boxer (Wayne) who returns to Ireland in the 1920s and upsets a simple community. Some contend it’s one of Wayne’s better roles, so check it out in May and see if you agree.

Spring is the perfect time to ease on down the road with 1978’s , a deeply weird yet entertaining contemporary (for the time) musical version of The Wizard Of Oz. If you’ve heard of the film you know it stars Diana Ross as Dorothy, Michael Jackson as Scarecrow, and Richard Pryor as The Wiz(ard). But did you know the film was written by Joel Schumacher and directed by Sidney Lumet? Again, The Wiz is a weird one, but it’s good family fun. Be prepared for ear-worm-worthy songs that will rattle in your head for weeks.

After James Gunn cleverly Easter egged Marvel’s popular cult character in Guardians Of The Galaxy, it seemed certain that a streamer would have jumped all over the chance to stream the much-maligned 1986 mega-bomb from producer George Lucas. Welp, better late than never; Prime Video is trotting out the Duck to brighten your spring viewing. Howard The Duck has its admirers, but then again so does every other bad movie. Maybe the world is more ready for a male duck/female human love connection in 2023. Get ready to pass judgment on May 1.

There’s a strong contingent of film fans who feel that Eddie Murphy was robbed of an Oscar nomination for his portrayal of, well, a bunch of characters in 1996’s . Admittedly, it’s an impressive, although dated, array of wildly diverse characters portrayed by Murphy, including the eponymous nutty professor, Sherman Klump, and his alter ego “Buddy Love,” Klump’s cranky uncle Cletus, Mama Anna, Ernie Klump, and Richard Simmons wannabe Lance Perkins. Heck, Murphy often played them all in the same scene to massive box office success but no awards glory.

If you’re already missing Apple TV+’s hit series Shrinking starring Jason Segel, you can get your Segel fix all over again with 2008’s rom-com . Who can forget one of the cringiest cry scenes ever featuring a fully frontal nude Segel (there’s a Shrinking joke in there somewhere) as well as the days when studios were pushing Mila Kunis and Kristen Bell as heirs apparent to Julia Roberts and Andie MacDowell in the rom-com realm. Forgetting Sarah Marshall is a funny film that also features Russell Brand at his Russell Brandiest and a small but memorable role by Paul Rudd.

Filmmaker Raoul Peck directed the truly outstanding 2016 documentary , which helped to bring more attention to the sadly not-better-known African American writer, playwright, essayist, poet, and activist James Baldwin. The doc is incredibly well done as Peck explores American civil rights, racism, and social injustice through the lens of Baldwin’s unfinished manuscript, Remember This House. Narrated by Samuel L. Jackson, I Am Not Your Negro is as insightful as it is powerful. A must-see, especially in today’s climate.

, Maria Schrader’s big-screen telling of the true story of New York Times journalists Megan Twohey and Jodi Kantor (played by Carey Mulligan and Zoe Kazan, respectively), who helped break the Harvey Weinstein scandal, had all the earmarks of an awards season winner. So, why did the film slip silently by viewers and critics alike? Well, let’s all find out on May 19 when Prime Video brings She Said to a movie night near you.

It may almost be summer on the calendar, but that doesn’t mean you can’t enjoy a festive little holiday season action comedy. David Harbour stars as an ass-kicking Santa Claus in 2022’s , which was surprisingly well-received by critics and a low-key hit with audiences. Catch director Tommy Wirkola’s film as it comes down the Prime Video chimney in May.

Is there nothing Chris Rock can’t do successfully? If you were going to say “writing and directing?” we’d say you’re wrong as the 2014 rom-com is a solid little indie charmer that leaned hard into its art film influences. Rock also stars as a stand-up comic who becomes an action movie star forced to spend the day with a surly film critic (Rosario Dawson) who panned the actor’s latest film, a passion project about the revolution in Haiti. The film is sure to win over even the staunchest of critics.

If you’re amongst the many suffering from the fact that Dwayne “The Rock” Johnson is oversaturating our lives, maybe now is a good time to harken back to 2003’s Peter Berg-directed action comedy . Indeed, if you’re sick of The Rock and his apparent ability to be everywhere all at once, you should be reminded of a time two decades ago when he used his charm and comedy chops to translate a massively successful professional wrestling career into movie stardom. In short, The Rundown is a hugely entertaining film that might help you to appreciate all that you have in The Rock.

Often overlooked or considered a missed opportunity in his move towards “More Serious Movies,” Steven Spielberg’s 1997 historical biopic is unfairly maligned. Perhaps the fact it’s stuck plumb in the middle of Schindler’s List (1993) and Saving Private Ryan (1998) means the film just pales a bit by comparison but, if you haven’t seen it, it’s well worth your time. Centered on a slave uprising in the mid-1800s, Amistad features great performances by Anthony Hopkins, Morgan Freeman, Matthew McConaughey, Djimon Hounsou, and the late, great Pete Postlethwaite.

A simply beautiful film, 1979’s doesn’t get nearly enough of the credit it deserves. Featuring gorgeous cinematography from the great Caleb Deschanel and a touching performance by Mickey Rooney, the Carroll Ballard-directed, Francis Ford Coppola-produced adventure film is about a boy (Kelly Reno) who is shipwrecked on a deserted island with a wild black Arabian stallion. The two forge an uneasy friendship and, upon the rescue, soon find themselves being trained to win horse races. A truly great family film, The Black Stallion will charm even the toughest filmgoers around.

Let’s all rejoice in the fact that seemingly everyone, everywhere, all at once is realizing that is a totally stand-up dude who has a specific onscreen niche where he shines. After decades of getting slagged, we have all come to realize that Keanu rules. While 1989’s may be a bit dated, it’s still a ton of fun and holds up for people of all ages. Granted, nostalgia factor aside, 2020’s Bill & Ted Face The Music wasn’t all that great, but the first film is a silly joy to behold.