The best movies leaving streaming at the end of May

Russell Crowe in The Insider holding a phone
Image: Buena Vista Pictures

An all-timer thriller and more great movies to watch this month

Summer’s around the corner — or maybe it’s already here, depending on the weather wherever you’re at. Either way, May is almost over, and that means movies leaving streaming services at the end of the month.

This month, we have two very different thrillers — one about corporate malfeasance, one about an evil box — an underrated video game adaptation, and a very silly comedy with a great cast. We’re also highlighting The Crow, with the new version starring Bill Skarsgård and FKA Twigs just a few months away.

Here are the best movies you should watch before they leave streaming this May.

Editor’s pick: The Insider

Al Pacino in The Insider. Image: Touchstone Pictures

Director: Michael Mann
Cast: Al Pacino, Russell Crowe, Christopher Plummer
Leaving Criterion Channel: May 31

In 1996, 60 Minutes ran a searing episode exposing the tobacco industry for intentionally adding dangerous chemicals to cigarettes and lying to the public. The episode relied on the testimony of whistleblower Jeffrey Wigand, the former vice president of research and development at a major tobacco company. And the story behind how that episode came to be (and how it nearly never aired) is fascinating, as documented in Michael Mann’s excellent thriller The Insider.

A powerful movie about the difficulties of working ethically inside a large corporation and what real heroism actually looks like, The Insider is one of Mann’s very best movies — and that’s an extremely high bar. Al Pacino and Russell Crowe star as CBS producer Lowell Bergman and the whistleblower Wigand, respectively, and the excellent supporting cast includes Christopher Plummer (as legendary 60 Minutes correspondent Mike Wallace), Philip Baker Hall, Gina Gershon, and Rip Torn. It’s a gorgeous movie to take in as well, with crisp cinematography from Dante Spinotti earning him one of the movie’s seven Oscar nominations — including Best Picture, Best Director, Best Screenplay, and the first of three consecutive Best Actor nominations for Crowe. —Pete Volk

Movies to watch leaving Netflix

Silent Hill

A still from the movie Silent Hill showing the “Welcome to...” sign shrouded in fog Image: Sony Pictures Entertainment

Director: Christophe Gans
Cast: Radha Mitchell, Sean Bean, Laurie Holden
Leaving Netflix: May 31

This movie doesn’t get the credit it deserves. Not only is it one of the best video game movies ever made, it’s also a very creepy (and gory) horror movie that does a great job of capturing the games’ mounting existential dread. You already know the premise: A girl gets lost in Silent Hill and someone else has to go rescue her, only to find all manner of untold horrors within the abandoned town. While there are bits and pieces of CGI that don’t quite hold up, the rest of this movie includes some truly terrifying creatures and sequences, and an absolutely devastating ending that few horror movies can match. —Austen Goslin

Movies to watch leaving Prime

The Crow

Brandon Lee as the crow holding a knife up to a stabbed person Image: Lionsgate Home Entertainment

Director: Alex Proyas
Cast: Brandon Lee, Ernie Hudson, Michael Wincott
Leaving Prime Video: May 31

There’s a new adaptation of The Crow coming around the corner this summer, so why not watch the original this month? While best known for the tragic death of star Brandon Lee, who was fatally shot in an accident during production, The Crow is an enduring neo-(goth-)noir classic for good reason. With a foreboding atmosphere via director Alex Proyas (Dark City) and the (very) dark source material, The Crow inspired a whole generation of goths.

And if you love Brandon Lee in this, check out some of the other movies in his all-too-short filmography. His previous two movies — Showdown in Little Tokyo and Rapid Fire — are both stellar. Like his father, he was one hell of a movie star whose life and career was cut all too short. —PV

Movies to watch leaving Max

The Box

Cameron Diaz, James Marsden, and Sam Oz Stone sit around their dining table, all looking at the box from The Box. Image: Warner Bros. Pictures

Director: Richard Kelly
Cast: Cameron Diaz, James Marsden, Frank Langella
Leaving Max: May 31

I have a vivid memory of The Box being marketed as a horror movie, but it really isn’t. After falling head over heels for his Southland Tales (and with Donnie Darko under my belt long before that), I wanted to complete my experience with the Richard Kelly filmography with his most recent feature, which was broadly rejected by critics and audiences alike but is nonetheless a fascinating movie. And I was rewarded for that decision, albeit with some qualms.

You know the basic premise. It’s been memed to death — a family receives a button that will give them a million dollars if they press it, but someone they don’t know will die. But that basic premise hides a much richer movie, a tense domestic drama that unwinds into a conspiracy thriller turned [redacted for spoilers]. Like Kelly’s other movies, The Box is filled with interesting images and is ripe for all sorts of metaphorical readings, even if it is less successful than his two previous features. I found myself quite frustrated with the ending, especially with regard to its relationship to disability, but it’s a fascinating and endlessly discussable thriller nonetheless. —PV

Movies to watch leaving Hulu


John Cena, Leslie Mann, and Ike Barinholtz in Blockers Photo: Quantrell D. Colbert/Universal Pictures

Director: Kay Cannon
Cast: Kathryn Newton, John Cena, Leslie Mann
Leaving Hulu: May 31

A hybrid sex comedy/generation-gap comedy from 30 Rock alum Kay Cannon, Blockers follows three parents who are trying to stop their daughters from losing their virginity on prom night... and also the three daughters trying to lose their virginity on prom night. It’s not nearly as conservative about young women having sex as the premise might have you believe, as the parents’ ridiculous overprotectiveness is often the butt of the joke, but the real strength is the cast: rising stars Kathryn Newton, Geraldine Viswanathan, and Gideon Adlon excel as the three main girls, while Leslie Mann, John Cena, and Ike Barinholtz are all great as the overbearing parents.

Often juvenile and not always funny, Blockers isn’t some great breakthrough moment in American comedy, but it is a fun time with a very game cast. The split between the parents and the children and their various problems and hang-ups is almost like an American version of Derry Girls. While Blockers lacks the emotional resonance of that Netflix show, it’s still an underrated Hollywood comedy during an era where very few of those have been worth talking about. —PV

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