Finding shows and movies to watch in May is the easy part. The month brings plenty of options on Netflix, Disney Plus, HBO Max, Hulu and more of the best streaming services. The harder task is setting aside time to binge them!
May’s streaming lineup is packed with stars, with new projects from Jessica Biel, Claire Danes, Tom Hiddleston, Zac Efron, Rebel Wilson, Colin Firth and John Mulaney. But the month’s biggest releases are coming out on the same day, as May 27 delivers the biggest pop-culture clash Stranger Things season 4 and Obi-Wan Kenobi dropping simultaneously. It’s the Upside Down vs. A Galaxy Far, Far Away. Clear your schedules for demogorgons and light sabers.
If you have different space-faring interests, Star Trek: Strange New Worlds expands the franchise by bringing back Captain Pike and Spock for more galaxy-exploring adventures. Meanwhile, drama lovers have the luxury of choice, from the true crime retellings Candy and The Staircase to the World War II thriller Operation Mincemeat to the relationship soap Conversations With Friends.
For laughs, Rebel Wilson returns to the big screen in Senior Year and the animated reboot of Chip ‘n Dale. Plus, two fan-favorite comedy series, Hacks and Girls5eva, are back for their second seasons.
Here’s our guide on what to watch in May 2022. For a more immediate binge, check out our picks for new movies and shows to watch this weekend.
The Circle season 4 (Netflix)
When to stream it: May 4
A lot of hand-wringing has occurred in the wake of Netflix’s recent subscriber loss, with a good deal of talk centered around the declining quality of the streamer’s shows. I’ve seen reality shows unfairly maligned in that discussion, but leave The Circle out of your mouth. It’s not only great content, but it’s one of the few shows that Netflix doesn’t dump-drop, which helps create buzz. The Circle should be emulated, not trashed.
Season 4 returns with host Michelle Buteau overseeing more social media shenanigans, as nine new contestants enter The Circle to play as themselves or as catfishing personas. They’ll compete to be named influencers, make alliances and avoid elimination, until one is crowned the winner of $150,000. — Kelly Woo
Watch it on Netflix
Girls5eva season 2 (Peacock)
When to stream it: May 5
Our favorite reunited girl group is back in the studio, hoping to find their second hit as they record a new album of their own music. Unfortunately, they've got a short window to produce it (who makes a whole album in six weeks?) and they're working in a confusing new music industry. For example: Their new producer isn't making things overtly sexual or awkward.
In the trailer for the new season, we've got plenty of shocking outfits and the best lines seem to be going to Gloria (Paula Pell) and Summer (Busy Phillips), though we're expecting the series is saving much more for the actual show. If you missed Girls5Eva the first time, now is a good time to catch up on the show that made us pay for Peacock. — Henry T. Casey
Watch it on Peacock
The Pentaverate (Netflix)
When to stream it: May 5
Netflix loves to declare it's doing big, bold things. And a new series called The Pentaverate is its latest big "event" project that it declares will rock the world. But unlike most of those things? The Pentaverate is a spinoff of 1993's So I Married An Axe Murderer. Yes, Mike Myers is back in this project he's not only starring in, but created and co-wrote. And, you guessed it — Myers is going full chameleon again, with at least eight (that we know of) characters.
The main character he's playing is Canadian journalist Ken Scarborough, who is down on his luck and wants to get his old job back. How will he do that? By exposing a plot that sounds straight out of Monty Python, as five men have secretly been influencing world events for what they believe is the greater good. Fortunately, Myers is surrounded by a strong supporting cast including Keegan-Michael Key, Ken Jeong and Debi Mazar. — HC
Watch it on Netflix
The Staircase (HBO Max)
When to stream it: May 5
Before the true crime documentary was the ascendant genre it is today, The Staircase captivated viewers (including myself) way back in 2004. French filmmaker Jean-Xavier de Lestrade chronicled the case of Michael Peterson, accused and eventually convicted of murdering his wife Kathleen.
Now, HBO Max is presenting a scripted, star-packed treatment, with Colin Firth playing Michael, Toni Collette as Kathleen and Sophie Turner as daughter Margaret. Even the documentary film crew are characters, which is apt as the eight-episode miniseries concerns itself with how storytelling affects subjectivity and whether the truth of the case can ever be known with certainty. — KW
Watch it on HBO Max
Star Trek: Strange New Worlds (Paramount Plus)
When to stream it: May 5
The final frontier is getting even more crowded, with Strange New Worlds representing the sixth Star Trek series made by Paramount Plus (and a seventh is on the way). It’s a spinoff of Discovery, after a major season 2 storyline featured USS Enterprise crew members Captain Christopher Pike (Anson Mount) and Spock (Ethan Peck).
Fans responded positively toward the characters, particularly Peck’s take on the iconic Vulcan, and thus, a new Star Trek was born. Strange New Worlds serves as a prequel to the original series, as canon has already established that Pike commands the Enterprise before James T. Kirk. As the title alludes, the crew — including First Officer Una Chin-Riley aka Number One (Rebecca Romijn), Cadet Nyota Uhura (Celia Rose Gooding) and Nurse Christine Chapel (Jess Bush) — explore uncharted parts of the galaxy. - KW
Watch it on Paramount Plus
Candy (Hulu)
When to stream it: May 9
The latest true crime drama literally involves an ax murderer. In 1980, suburban Texas housewife Candy Montgomery was accused of murdering best friend Betty Gore after having an affair with Gore’s husband. Gore was brutally maimed 41 times with an ax, but Montgomery pled self-defense and was acquitted. You cannot make this stuff up.
Jessica Biel stars as Candy, Melanie Lynskey plays Betty, Pablo Schreiber as Betty’s husband Allan and Timothy Simons as Candy’s husband Pat. The miniseries is airing as a five-night event, an unusual and old-school choice but one that mimics the way the notorious case mesmerized the public at the time. - KW
Watch it on Hulu
Operation Mincemeat (Netflix)
When to stream it: May 10
The Mr. Darcy’s unite! Colin Firth and Matthew Macfayden both had memorable turns as the brooding hero of Jane Austen’s Pride and Prejudice, and now they team up for this World War II thriller about a preposterous but real espionage deception.
Ewen Montagu (Firth) and Charles Cholmondeley (Macfayden) are British intelligence officers who hatch a hare-brained scheme to gain ground in German-occupied Italy. They plant a corpse in the sea carrying fake documents about a campaign in Greece in an effort to hide their true plan: an Allied invasion of Sicily. It sounds ludicrous, but Operation Mincemeat could be a turning point in the fight against Hitler. - KW
Watch it on Netflix
Hacks season 2 (HBO Max)
When to stream it: May 12
May the Jean Smart-aissance never end. The actress already won one Emmy for her portrayal of stand-up comedy queen Deborah Vance on Hacks and a second trophy could be on her mantle by the end of the year.
Deborah and her acerbic tongue are hitting the road in season 2, along with millennial comedy writer Ava (Hannah Einbinder). Deb’s final Las Vegas show was a bust, but she is excited to test out new material in clubs across the country. She’s finally accepted that it’s time to refresh her act for younger audiences, even if she isn’t quite ready to give Ava much credit. Their relationship has settled into some harmony — though they’re still constantly needling each other with jokes — which is threatened by the looming revelation that Ava sent a slanderous, tell-all email about Deborah to some TV producers. - KW
Watch it on HBO Max
The Essex Serpent (Apple TV Plus)
When to stream it: May 13
What if Nessie was real? The Essex Serpent isn't a Loch Ness Monster story, but it sure feels adjacent. When a creature surfaces, the general public is disbelieving so it's up to London widow Cora Seaborne (played by Clare Danes) to investigate it all. Along the way, she actually strikes up something of a friendship with the local pastor (Tom Hiddleston), who surprises her with his respect for science and skepticism.
Unfortunately, Cora's hunt for this Essex serpent goes bad in a somewhat predictable way: Accusations that she's brought the beast here set this town into full witch hunt-mode. An adaptation of Sarah Perry's award-winning novel of the same name, The Essex Serpent is a six-part series whose first two episodes debut together. — HC
Watch it on Apple TV Plus
Firestarter (Peacock)
When to stream it: May 13
What happens when you take a superhero movie but make it horror? You get Firestarter, a movie about a little girl named Charlie (newcomer Ryan Kiera Armstrong) who has a big secret: she's producing fire at a rate that makes you wonder if Marvel would cast her as a female Human Torch in the upcoming Fantastic Four MCU movie.
Charlie's father Andy (Zac Efron) is doing his best to train her to keep her pyrokinesis under control, but it doesn't exactly go well from what we see. Peacock's pulling an HBO Max move by debuting the Firestarter the same day it hits theaters, May 13. — HC
Watch it on Peacock
The Kids in the Hall (Prime Video)
When to stream it: May 13
The last revival we expected is actually happening, since Amazon (which the new episodes equate to the devil) is paying Dave Foley, Bruce McCulloch, Kevin McDonald, Mark McKinney and Scott Thompson an undisclosed amount of money to bring their off-kilter brand of comedy back from the dead.
The trailer also pokes fun at the whole idea of bringing this show back, as they appear to be as surprised by the revival as anyone. Other targets include The New Yorker writer Jeffrey Toobin's fireable offense, toxic office environments, TV shows with bizarre premises and … well, stuff we're not going to write here. — HC
Watch it on Prime Video
Senior Year (Netflix)
When to stream it: May 13
Fresh off a year of focusing on personal health, Rebel Wilson's returning to the public eye on the small screen with a comedy about the oddest senior year ever. In what looks part Never Been Kissed and part Freaky Friday, Stephanie Conway (Wilson) wakes up from a coma induced by a freak cheerleading accident that took place 20 years ago. And, of course, she finds that high school in 2022 is a lot different than it was in 2002.
Everyone who is waiting for The Afterparty season 2 may tune in to see Sam Richardson as love interest Seth and Zoe Chao as rival student Tiffany, but we're mostly curious about Alicia Silverstone, whose TBA role has yet to be revealed. — HC
Watch it on Netflix
Conversations With Friends (Hulu)
When to stream it: May 15
We’ve already met Normal People; now, it’s time to have Conversations With Friends. After the success of one Sally Rooney novel adaptation, Hulu is hoping to go two for two. They’ve even re-hired most of the creative team behind Normal Team to shepherd Conversations, including director Lenny Abrahamson and co-writer Alice Birch. And like the first adaptation, this one focuses on the romantic entanglements of young Irish adults.
Frances (Alison Oliver) is a smart, observant but somewhat inexperienced 21-year-old college student who is still close to her outspoken ex-girlfriend Bobbi (Sasha Lane). At a local poetry event, they meet an older writer, Melissa (Jemima Kirke), who is married to handsome actor Nick (Joe Alwyn). As Bobbi and Melissa flirt, Frances and Nick begin a surprising but intense affair that could upend all their relationships. - KW
Watch it on Hulu
Chip ‘n Dale: Rescue Rangers (Disney Plus)
When to stream it: May 20
Earlier this week, while talking to my Tom's Guide colleagues, I was asked to confirm that the Chip ‘n Dale: Rescue Rangers movie actually looks good. Because the trailer suggests we're going to get a much better film than anyone could have anticipated. All that good will is owed to the fact that the film actually feels like Chip and Dale actually grew up with the rest of us.
Not only is the franchise unafraid of making Chippendales jokes, but these characters actually feel more whole. Chip, for example, is now working in insurance and has isolated himself from reality after their show got canceled. Oh, and Chip is voiced by John Mulaney, Dale is voiced by Andy Samberg, while Will Arnett is voicing a villainous Peter Pan. — HC
Watch it on Disney Plus
Night Sky (Prime Video)
When to stream it: May 20
Sissy Spacek and J.K. Simmons star in this surprising new Prime Video series as a couple who are proving you can teach an old dog a new trick: interstellar travel. Yes, one night Irene (Spacek) reveals a secret to husband Franklin (Simmons): She's got the best view of the galaxy.
Soon enough, though, gossips in the neighborhood are concerned with their weird behavior, and a visitor found in their secret room might actually be an alien. Combined with Prime Video's other supernatural series Outer Range, it certainly feels like the service is hitting a stride as the place you go to be amazed. — HC
Watch it on Prime Video
Now and Then (Apple TV Plus)
When to stream it: May 20
College reunions are awkward enough, but Now and Then goes even further when five friends from the Class of 2000 reunite for their twentieth, only to be haunted by a dark secret they've all kept. Will they pay the blackmailer? Or will their secret be outed?
Since these graduates have gone on to lead somewhat successful lives — they're being bribed for $1 million each for a reason — they're probably hoping it results in the former. Flora (Rosie Perez), a local cop still trying to solve the original case, doesn't realize it but she's working for the latter to come true. — HC
Watch it on Apple TV Plus
Obi-Wan Kenobi (Disney Plus)
When to stream it: May 27
And back we go to Tatooine. The galaxy far, far away seems to revolve around the dusty desert planet, home to the Skywalkers and, for a time, Obi-Wan Kenobi. The titular Jedi knight is the protagonist of this series, set 10 years after Revenge of the Sith.
Ewan McGregor reprises his role from the prequel movies, with Hayden Christensen also returning as Anakin Skywalker (now Darth Vader). Still hunted by the Empire, Obi-Wan hides on Tatooine and watches over his charge, young Luke Skywalker. But as inquisitors search the sector for him, the Jedi is drawn out of seclusion to battle the dark side once again, which may result in a showdown with his apprentice-turned-enemy. - KW
Watch it on Disney Plus
Stranger Things season 4 volume 1 (Netflix)
When to stream it: May 27
Going back to Hawkins sounds like a nightmare, and it looks like one too, thanks to a new villainous entity and the appearance of horror legend Robert Englund as a man without eyes. It's all leading to a war from the Upside Down, which Eleven (Millie Bobby Brown) has been told she has to fight. The only problem? Well, she doesn't have her powers. Speaking of powers? Max (Sadie Sink) is flying. We're not sure why or now, but it seems to be tied to the grief over her dead brother.
Meanwhile, in frigid Russia, Hopper (David Harbour) is in a prison and forced to fight demogorgons. And since Stranger Things season 4 is being told in two parts, we have the hunch that he winds up back in town at the end of Vol. 1 with the tips the gang needs to stop these beasts. — HC
Watch it on Netflix
Pistol (Hulu)
When to stream it: May 31
The rock and roll revolution will be televised, er, streamed. The limited series Pistol celebrates the rise of punk culture, led by the iconic band the Sex Pistols. Based on founding member and guitarist Steve Jones’ memoir, the drama chronicles how a group of working class kids with “no future” shook the British establishment to its core. Toby Wallace stars as Jones, with Anson Boon as vocalist John Lydon, Louis Partridge as Sid Vicious, Thomas Brodie-Sangster as manager Malcolm McLaren and Maisie Williams as style setter Jordan.
What is sometimes forgotten about the Sex Pistols is how short-lived the band was. They last just three chaotic, game-changing, completely bonkers years. But even in that brief period of time, they changed the face of music, art and fashion forever. - KW
Watch it on Hulu
