Guide to Streaming in May

Watching plan for May: catch up on the 400 marquee series (approximate number) that dropped near the end of April and then hunker down. The first couple weeks of this upcoming month offer a mercifully small number of must-watch shows … but that’s just the calm before the storm. By the end of the month, two of the biggest releases on the calendar will have premiered on the same day. So get ready while you can. And use this guide as a helper, if you want, What’s New to Streaming in March – A selected list of movies and TV shows coming this month that The Ringer is very excited about.

Terminator 2: Judgment Day (May 1, HBO Max)

Alan Siegel: The juxtaposition of warmth and spectacle is what elevates Terminator 2 above nearly all other ’90s popcorn flicks. But that somehow undersells its appeal and influence. Industrial Light & Magic’s cutting-edge visual effects, a Kevlar-tough woman as the lead, dozens of memorable one-liners, and terrifyingly prescient themes combined to form a blockbuster that pushed the limits of the medium. The top-grossing movie of 1991 escalated a big-screen arms race that’s played out in American cineplexes every summer since.

The Circle, Season 4 (May 4, Netflix)

Shea Serrano: Part of what makes The Circle so great is how despite early assumptions that a show like this would lean into the idea that the loneliness heavy internet users might feel has been baked into their bones, it somehow does the opposite. Once the novelty wears off several episodes in, everything and everyone begins to feel ultra-humanized. The isolation somehow begins mushing people together through their TV screens. It’s incredible to watch happen. There are of course fun and funny moments on the episodes that speed the show forward (the guy pretending to be a woman, for example, is routinely invited into woman-only chats, and every single time he gets invited in he’s two or three sentences away from tipping his hand), but there are also big philosophical moments that ground everything in a I Wasn’t Expecting This Water to Get So Deep way. Watching a catfish having to process why they’ve chosen to catfish feels like peeking inside someone’s diary.

The Staircase (May 5, HBO Max)

Andrew Gruttadaro: After winning an Academy Award for his 2001 HBO documentary Murder on a Sunday Morning, Jean-Xavier de Lestrade decided to tell the other side of the story. Murder had followed the story of Brenton Butler, a Black, lower-class 15-year-old who had been wrongfully accused of murder; de Lestrade still wanted to examine the American criminal justice system, specifically in relation to murder trials, but this time through the lens of a white person, one wealthy enough to be able to afford the best defense possible. He and his team started reviewing cases that fit the criteria, and after 300 cases and about five months of research, they found Michael Peterson.

Girls5Eva, Season 2 (May 5, Peacock)

Alison Herman: Like all good themes, Girls5Eva’s is a perfect capsule of the show it introduces. Deceptively silly and loose, the tune also has an airtight grip on its satirical subject: late-’90s girl groups and what happens to their members, and all women in show business, when they reach middle age. A Spice Girls–type quintet who peaked in the last millennium, Girls5Eva gets an unexpected boost when their biggest (read: only) hit is sampled by the Gen Z rapper Lil Stinker. Sensing opportunity, the surviving members of the group—the “fun one” swam off the edge of an infinity pool back in the aughts—resolve to turn their second wind into a full-fledged comeback.

The Challenge: All Stars, Season 3 (May 11, Paramount+)

Randall Coburn: The Challenge: All Stars is a spinoff of MTV’s resilient competition series. It reunites the show’s bygone stars for a game that reflects the franchise’s latter-day evolution from oceanside romp to honest-to-goodness athletic contest. (Seriously, the grueling cardio and gut-dropping psych-outs of today’s Challenges barely resemble those bygone beach games.) But it also has larger significance: The series is an indicator of MTV’s strategy on the nascent streamer, which last year rose from the ashes of CBS All Access after CBS merged with Viacom, MTV’s parent company. The raucous bundle of viral fail videos that is Rob Dyrdek’s Ridiculousness continues to consume the network’s airwaves, so MTV appears to be using Paramount+ to win back the Gen X and millennial audiences it lost in its efforts to woo younger generations.

Hacks, Season 2 (May 12, HBO Max)

Herman: Hacks isn’t just a two-hander. It’s also a study in the strange bubble that sets in around the rich and famous, from the workaholic business manager to the personal blackjack dealer to the jaded adult daughter. Jean Smart is the center of this hermetically sealed universe and rightly earned an Emmy for Season 1. Still, Hacks is a stealth ensemble, and a tribute to how much more goes into a legend’s career than one fabulous diva on a stage.

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