11 Films To Watch In May: 'The Vast of Night,' 'All Day and a Night' & More

For many of us (though we New Englanders have had to suffer a bit longer) it’s officially Spring, which typically means more time to spend outdoors and less time to spend catching up on films. Considering the state of things though, we won’t jump to that conclusion too quickly. May isn’t rich with new releases, but there are plenty of gems among them including a film that’s already debuted on Netflix to positive reviews, a re-scheduled Issa Rae and Kumail Nanjiani comedy and a final return of the “The Trip” duo Steve Coogan and Rob Brydon. There’s also plenty of documentaries to dive into that are being given the chance to shine as well as very niche, genre films that might be able to get more focus when they aren’t battling it out with tentpole summer blockbuster films that typically would have already been in full swing. Still, there’s plenty to enjoy and a vast display of genre and styles to keep people engaged.

READ MORE: 100 Most Anticipated Films Of 2020

The Half of It
Cast: Leah Lewis, Daniel Diemer, Collin Chou
Synopsis: A shy, introverted student helps the school jock woo a girl whom, secretly, they both want.
What You Need to Know: It’s been 16 years since director Alice Wu released her first feature film, “Saving Face,” and fans have been waiting anxiously for her return to the medium. Highly influential in its depiction of sexuality, aging and womanhood as well as simply a tightly written and perfectly executed romantic-comedy, it’s one of the best of its genre of the last 20 years. Her follow up, “The Half of It” tackles similar themes of young women – this time a teenage girl – confronting their sexuality by way of helping a boy try and win the affections of a girl they both like and being an Asian American teenager in a middle America, Trump friendly town. The platonic love story is something to celebrate and the film just recently won the Founders Award for Best Narrative Feature at the 2020 Tribeca Film Festival.
Release Date: May 1st

All Day and a Night
Cast: Jeffrey Wright, Ashton Sanders, Yahya Abdul-Mateen II
Synopsis
: A young man embarks on a journey of self-discovery after landing in the same prison as his father.
What You Need to Know: One of the greatest pulls of “All Day and a Night” lies in the casting of the tremendous Ashton Sanders. A continuing up and comer since his breakthrough in “Moonlight,” he co-stars alongside the similarly impressive Jeffrey Wright as father and son. Directed by Joe Robert Cole who co-wrote “Black Panther” alongside director Ryan Coogler, the film marks his first feature film. The film hasn’t received the strongest buzz surrounding its release but with a cast this strong and yet another chance to showcase Sanders as the undeniable talent he is, it might be worth a quick watch on Netflix.
Release Date: May 1st on Netflix

The Wretched”
Cast: Piper Curda, John-Paul Howard, Richard Ellis
Synopsis
: A defiant teenage boy, struggling with his parent’s imminent divorce, faces off with an old witch who has possessed the neighbor next door.
What You Need to Know: Helmed by first time directors Brett Pierce and Drew T. Pierce and starring some relative newcomers in leading roles, “The Wretched” is an unpolished springtime horror. With magical-realism and fantastical elements to go alongside the strictly horror atmosphere of the film, it’s a relatively big swing for the first time filmmakers who also penned the screenplay together.
Release Date: May 1st on VOD and Amazon Prime

Natalie Wood: What Remains Behind”
Cast: Natasha Gregson Wagner, Mia Farrow, Elliot Gould
Synopsis: Interviews, home movies, photographs and diaries offer insight into the remarkable life and career of actress Natalie Wood.
What You Need to Know: Natalie Wood’s legacy exists in two areas. First, is the immense talent she displayed at a young age and continued to do so through the remainder of her cut-short
career. The second, is her tragic and mysterious death that to this day, nearly 40 years later, is still discussed regarding who was there and who may have been complicit in her death. In “Natalie Wood: What Remains Behind,” director Laurent Bouzereau (who also directed the documentary “Roman Polanski: A Film Memoir”) looks beyond the celebrity image to find out more about the actress and her life, aided by Wood’s daughter Natasha Gregson Wagner and other personal accounts.
Release Date: May 5th on HBO

How to Build a Girl
Cast: Beanie Feldstein, Alfie Allen, Paddy Considine, Emma Thompson
Synopsis
: The film follows the growth of Johanna Morrigan, starting as a teenager living with her working-class family on a council estate in England, as she becomes a popular but conflicted music journalist.
What You Need to Know: Following her turns in supporting roles in “Lady Bird,” “Neighbors 2” and “What We Do in the Shadows” along with her leading role in last year’s “Booksmart,” we are fully on the Beanie Feldstein should be in everything train. This, seemingly, would make the release of “How to Build a Girl” something worthy of support but there are plenty of people who find Caitlin Moran’s (who wrote the book the film is based on as well as adapting the screenplay) brand of feminism trying. Hopefully the film will manage to smooth out any of the rough patches and allow star Feldstein and an impressive supporting cast carry the story. Directed by Coky Giedroyc, this is her first feature film since 1999’s “Women Talking Dirty.”
Release Date: May 8th on VOD

Spaceship Earth
Synopsis: “Spaceship Earth” is the true, stranger-than-fiction, adventure of eight visionaries who in 1991 spent two years quarantined inside of a self-engineered replica of Earth’s ecosystem called BIOSPHERE 2. The experiment was a worldwide phenomenon, chronicling daily existence in the face of life-threatening ecological disaster and a growing criticism that it was nothing more than a cult.
What You Need to Know: Despite the audacious nature of this story, there’s plenty of those who are completely surprised by the events that transpire throughout the upcoming documentary “Spaceship Earth.” Directed by Matt Wolf who helmed the 2014 under-seen gem “Teenage,” the film follows real-life events that grow increasingly bizarre. There’s also no denying the odd timeliness of the story about a group of humans who choose to quarantine themselves in order to try and better their world. Perhaps almost too on the nose for the time being, though the psychedelic coloring of the poster is enough to guarantee that while dealing with some heavy topics, “Spaceship Earth” won’t fail to be entertaining.
Release Date: Hulu, VOD, virtual cinemas, and participating drive-ins on May 8

The Painter and the Thief
Synopsis: Desperate for answers about the theft of her 2 paintings, a Czech artist seeks out and befriends the career criminal who stole them. After inviting her thief to sit for a portrait, the two form an improbable relationship and an inextricable bond that will forever link these lonely souls.
What You Need to Know: Yet another film that seems too odd to be true, “The Painter and the Thief” made its debut at this year’s Sundance Film Festival and was met largely with positive responses. Confounding in its ability to move you while centering itself on such a bizarre premise, it would be easy to read the synopsis and assume that it was a fictional narrative. Directed by Benjamin Ree in his debut feature film, it will drop on Hulu later this month.
Release Date: May 22nd on Hulu

The Lovebirds
Cast: Issa Rae, Kumail Nanjiani, Anna Camp
Synopsis: A couple experiences a defining moment in their relationship when they are unintentionally embroiled in a murder mystery. As their journey to clear their names takes them from one extreme circumstance to the next, they must figure out how they, and their relationship, can survive the night.
What You Need to Know: The first major release to make the jump to a streaming platform instead of simply pulling the film altogether or rescheduling, “The Lovebirds” had already amassed a decent amount of hype prior to the move, with a scheduled premiere at this year’s SXSW. Stars Issa Rae and Kumail Nanjiani are two of the most active and engaging voices in comedy today and pairing them together is a masterstroke. What also helps in building the excitement for fans of both is director Michael Showalter who last directed Nanjiani in the 2017 romantic-comedy “The Big Sick,” making it the second collaboration between the pair. We’ve seen films that have tackled similar storylines in the past but the talent on board makes it feel fresh.
Release Date: May 22nd on Netflix

Inheritance
Cast: Lily Collins, Simon Pegg, Connie Neilson
Synopsis
: A patriarch of a wealthy and powerful family suddenly passes away, leaving his wife and daughter with a shocking secret inheritance that threatens to unravel and destroy their lives.
What You Need to Know: In director Vaughn Stein’s second outing with Simon Pegg, he once again channels his energy into creating a modern twist on a classic genre. Lily Collins stars this time around a young woman left to untangle the mess her family has left themselves in and is hopefully a role that fully captures her star quality. Written by Matthew Kennedy in his first feature film screenplay, the film was previously expected to premiere at the 2020 Tribeca Film Festival.
Release Date: May 22nd on VOD

The Trip to Greece
Cast: Steve Coogan, Rob Brydon
Synopsis
: Funnymen Steve Coogan and Rob Brydon travel to restaurants, hotels and ancient landmarks in Greece.
What You Need to Know: It’s quite amazing just how long the legs of this relatively thin premise were. A four-part series of films which include “The Trip,” “The Trip to Italy,” “The Trip to Spain” and now “The Trip to Greece,” they’ve covered much mileage with a plot that begins and ends with fictionalized versions of Steven Coogan and Rob Brydon riffing and eating mouth-watering meals in beautiful locales. All directed by Michael Winterbottom and first airing as short series, what they may lack for structural substance they make up for in the true give and take chemistry between Coogan and Brydon with hints of pathos about aging, isolation and career ambitions helping give weight to what might’ve been a rudderless series of films. Instead, they aren’t just feasts for the eyes but also enjoyable stories in their own right.
Release Date: May 22nd on VOD

The Vast of Night
Cast: Sierra McCormick, Jake Horowitz, Gail Cronauer, Bruce Davis
Synopsis
: In the 1950s, two kids search for the source of a mysterious frequency that has descended on their town.
What You Need to Know: The responses to director Andrew Patterson’s “The Vast of Night” have been positive since it’s premiere at the 2019 Slamdance Film Festival and the buzz only grew as it made the festival rounds for the remainder of the year. Regardless of good reactions or not though (which certainly don’t hurt) there would have been natural intrigue regarding the film for the premise alone which is unabashedly a genre and period piece. It’s quite the ambition undertaking for a first-time feature filmmaker but Patterson and screenwriters James Montague and Craig W. Sanger made great use of the natural eeriness the subject matter and time period produce.
Release Date: May 29th on Amazon