May 2026 is officially the season of transformation in Toronto. From the grand opening of new outdoor concert stadiums to the revival of cultural landmarks and the launch of sophisticated new nightlife residencies, the city is vibrating with fresh energy as the flowers bloom. Here is your comprehensive entertainment guide to the best of May.
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This is your latest monthly entertainment guide for May 2026, of what’s available to stream, binge, or watch live near you.
ON SCREEN
Wuthering Heights
Emerald Fennell’s moody, gothic reimagining of Emily Brontë’s classic novel makes its highly anticipated movie premiere on Crave, HBO, and Max this May 1. Starring Margot Robbie and Jacob Elordi, this adaptation leans heavily into the atmospheric tension and destructive passion of Cathy and Heathcliff, bringing a modern cinematic flair and raw emotional intensity to the legendary literary tale of revenge and obsession.
Swapped
Michael B. Jordan and Juno Temple lead this high-concept animated body-swap comedy that arrives on Netflix on May 1, exploring the “grass is greener” trope with a wild, naturalistic twist. The story follows two unlikely forest companions, a predator and its natural prey, who wake up in each other’s bodies and must navigate their natural instincts to survive while finding a way back to their original forms.
Miss You, Love You
This marquee romantic drama premieres on HBO and Max on May 1 as a profound exploration of the intimacy and unavoidable strain of long-distance connection in the modern age. The film has garnered significant buzz for its realistic, unvarnished depiction of modern relationships and the digital bridges used to keep people together, questioning whether love can truly transcend physical and emotional gaps.
The Boss / El Encargado
The Season 4 premiere of the acclaimed series arrives on Disney+ (and Hulu in the US) on May 1, continuing to follow the manipulative yet charming building manager as he navigates the complex social hierarchies of his apartment complex. The show remains a standout for its sharp social commentary and dark humour, making it a must-watch for those who enjoy character-driven international dramas.
Lord of the Flies
This new limited series adaptation of William Golding’s classic novel arrives on Netflix on May 4, reimagined for a contemporary audience with a focus on modern social dynamics. The story explores the dark, psychological descent into savagery when a group of private school students is stranded on a remote island, offering a gritty look at the fragile power structures that emerge in the absolute absence of authority.
Citadel
The high-stakes global espionage thriller returns for its second season on Prime Video this May 6, ramping up the action for its elite, memory-wiped spy agency. After the explosive revelations of the first season, Mason and Nadia must navigate a fractured landscape of shifting loyalties and deep-seated betrayals to stop a rising shadow threat.
Bon Cop, Bad Cop
This highly anticipated Crave Original series officially premieres its first episodes on Crave on May 7, expanding the beloved Canadian film franchise into a full-scale television production. The show continues the bicultural and bilingual friction between officers from Ontario and Quebec as they tackle a fresh criminal conspiracy across Canada.
Send Help
Directed by horror maestro Sam Raimi, this survival thriller arrives on Disney+ on May 7, featuring Dylan O’Brien and Rachel McAdams as two strangers stranded on a remote island after a catastrophic plane crash. The film explores their struggle to overcome both the unforgiving elements and their own dark secrets, blending high-tension survival with deep psychological mystery.
RuPaul’s Drag Race All Stars
Season 11 kicks off with a special two-episode premiere on Crave and Paramount+ on May 8, bringing legendary queens from past seasons back to the workroom. The competition promises to be fiercer than ever as the queens prove they have the charisma, uniqueness, nerve, and talent to claim their place in the Hall of Fame.
Jennifer’s Body
This cult classic horror-comedy joins the Netflix library on May 8, offering a dose of sharp-witted, feminist subtext to the spring season. The story follows a possessed high school cheerleader who develops an insatiable appetite for her male classmates, leaving her best friend to find a way to stop the carnage before it consumes the entire town.
The Punisher: One Last Kill
Jon Bernthal reprises his role as Frank Castle in this Marvel Special Television Presentation, debuting on Disney+ on May 12. This standalone story marks a return to gritty, grounded action as the vigilante is pulled out of hiding for a mission that is deeply personal, forcing him to confront the ultimate cost of his past actions.
Good Omens
The third and final season concludes the whimsical adventures of Aziraphale and Crowley on Prime Video starting May 13. This final chapter sees the unlikely duo teaming up one last time to prevent a cosmic disaster that threatens both heaven and hell, all while maintaining their complicated, centuries-old friendship.
Off Campus
This Season 1 premiere adapts Elle Kennedy’s popular romance novels, arriving on Prime Video on May 13. The story follows the “opposites attract” dynamic between a serious music student and an elite college hockey player, blending the intensity of competitive sports with the emotional complexities of young love.
On the Roam: Season Two
Season 2 of Jason Momoa’s cinematic docuseries premieres on HBO, Max, and Crave on May 14, following the actor as he travels the country on his motorcycle to meet master craftspeople. The series explores the intersection of art and adventure, celebrating traditional craftsmanship and the personal stories behind these rare skills.
28 Years Later: The Bone Temple
Adding a terrifying new chapter to the post-apocalyptic horror saga, this film makes its streaming debut on Crave on May 15. The story follows survivors seeking refuge in a remote mountain sanctuary who realize that the infection has evolved, forcing them to make impossible choices to preserve the human race.
Dutton Ranch
This modern-day Yellowstone spin-off premieres on Paramount+ on May 15, focusing on Beth Dutton and Rip Wheeler as they fight to protect their legacy in Montana. The series serves as a crucial bridge in the overarching narrative, exploring the brutal decisions required to maintain the ranch against corporate encroachment.
Welcome to Wrexham: Season 5
Season 5 of the heartwarming football docuseries returns to Disney+ on May 15 to follow owners Rob McElhenney and Ryan Reynolds. The new season focuses on the team’s latest promotion push and the deep emotional connection between the club and the community that supports it through every win and loss.
Tom Clancy’s Jack Ryan: Ghost War
John Krasinski returns in a feature-length movie premiere arriving on Prime Video on May 20. The plot finds Ryan reluctantly thrust back into espionage when an international covert mission unravels a deadly conspiracy, forcing him to confront a ghost from his past to maintain global stability.
The Boroughs
Executive produced by the Duffer Brothers, this supernatural mystery series debuts on Netflix on May 21. Set in a tranquil retirement community, a group of unlikely geriatric heroes must band together to stop an otherworldly threat from stealing the one thing they don’t have much of: time.
Alien: Romulus
This atmospheric sci-fi horror film makes its streaming debut on Disney+ (and Hulu in the US) on May 21. Set between the first two films of the franchise, the story follows a group of young space scavengers who come face-to-face with a Xenomorph on a derelict station, recapturing the claustrophobic dread of the original.
SkyMed: Season Four
Season 4 of the high-altitude medical drama continues on Paramount+ starting May 21, following the pilots and nurses of an air ambulance service in Northern Canada. The new season dives deeper into the personal sacrifices and professional risks taken by the crew during intense rescues in the unforgiving wilderness.
The Bride!
Starring Maggie Gyllenhaal and Christian Bale, this stylized reimagining of monster lore premieres on Crave on May 22. Set in a 1930s-inspired gothic landscape, the tale follows a lonely creator who builds a companion, exploring deep themes of identity and bodily autonomy.
Josh Johnson: Symphony
This new original comedy special premieres on HBO, Max, and Crave on May 22, highlighting one of the most unique voices in stand-up today. Josh Johnson brings his sharp wit and observational humor to the stage, blending personal storytelling with a rhythmic perspective on the absurdities of modern life.
Spider-Noir
Nicolas Cage makes his live-action debut as a grizzled private investigator in 1930s New York, with the series premiering on Prime Video and MGM+ on May 27. The show explores a darker corner of the Marvel multiverse, following an aging hero who must confront a city full of shadows and corruption.
House of the Dragon
A special release of the epic series featuring American Sign Language (ASL) interpretation arrives on HBO, Max, and Crave on May 29. This initiative allows the deaf and hard-of-hearing community to experience the political intrigue and dragon battles of the Targaryen civil war with integrated, high-quality interpretation.
AFI Life Achievement Award: Eddie Murphy
The month concludes on Netflix on May 31 with a star-studded tribute celebrating the legendary career of a comedy icon. This special features testimonials from Hollywood’s biggest names to honour Murphy’s lasting impact on stand-up and film, providing a fitting finale to a massive month of entertainment
ON STAGE
Moulin Rouge! The Musical
Baz Luhrmann’s revolutionary film comes to life in a theatrical celebration of truth, beauty, freedom, and love when “Moulin Rouge! The Musical” takes over Toronto April 22-May 10. This 10-time Tony-winning production transforms the theatre into a decadent Parisian nightclub filled with over 70 pop hits. It is a sensory-overload experience and remains the toughest ticket to get in the Entertainment District.
& Juliet
& Juliet continues its hit run at the Royal Alexandra Theatre throughout the month, proving to be one of the city’s most enduring musical hits. This production reimagines the ending of Romeo and Juliet through the lens of modern pop hits by Max Martin, turning the classic tragedy into an empowering celebration of life, independence, and the joy of finding one’s own voice.
La Notte
La Notte launches at Primadonna on Thursday, May 7, and continues to bring a touch of old-world glamour to King West every Thursday night. Juno Award–winning artist Sean Jones takes up a live music residency that reimagines the traditional night out, blending high-end dinner and sophisticated cocktails in a setting where the live music isn’t just background noise — it is the main event.
Young, Gifted, and Black
Young, Gifted, and Black takes the stage at Factory Theatre from May 11 to 31 as a centrepiece of the spring season. Part of the Obsidian Theatre program, this showcase highlights powerful new voices and urgent storytelling from the next generation of Black artists in Canada, providing a platform for diverse narratives that challenge and inspire local audiences.
Toronto Confessions: Love It or Hate It
Toronto Confessions: Love It or Hate It takes over Second City on May 14 for a one-night-only storytelling event. Presented by the Museum of Toronto, this candid evening features public figures like Jeanne Beker, Tynomi Banks, and Kwame McKenzie sharing honest, unfiltered takes on living in the city right now, hosted by CBC’s Elamin Abdelmahmoud to explore what’s working and what isn’t in our changing metropolis.
The Division
The Division has been extended at Crow’s Theatre due to overwhelming popular demand, with new dates now available from May 18 to 24. This production has been praised for its tight, intellectual script and compelling look at the social tensions and shifting loyalties within a community facing an unprecedented crisis, making it one of the most talked-about plays of the year.
Imagine Dragons
Imagine Dragons officially kicks off the outdoor season on May 21 at the newly rebranded RBC Amphitheatre (formerly Budweiser Stage). As their only North American amphitheatre performance of the year, the show is expected to be a massive production featuring their signature anthemic sound and a high-energy stage presence that will set the tone for the summer concert season.
Bruno Mars
Bruno Mars launches the brand-new Rogers Stadium at Downsview Park with a five-night residency beginning May 23. “The Romantic Tour” serves as the inaugural event for the massive 50,000-seat outdoor venue, marking a historic moment for live music in the city and bringing Mars’ world-class showmanship to a scale Toronto hasn’t seen in years.
Khalid
Khalid brings his “It’s Always Summer Somewhere Tour” to the RBC Amphitheatre on May 24 for a night of smooth, soulful vibes. This R&B performance is the perfect soundtrack for a late May evening by the lake, featuring hits from across his discography in an intimate outdoor setting that highlights his velvet vocals and relatable songwriting.
Summer Walker
Summer Walker arrives at Scotiabank Arena on May 26 for her highly anticipated “Still Finally Over It Tour.” Fans can expect a soulful evening featuring her signature R&B hits and intimate storytelling, marking one of the month’s most significant musical events for fans of contemporary soul and raw, honest lyricism.
Kid Cudi
Kid Cudi performs at the RBC Amphitheatre on May 26 as part of “The Rebel Ragers Tour 2026,” a show that promises to be a visual and sonic trip. Known for his genre-bending sound and cinematic stage presence, Cudi’s return to Toronto is one of the most anticipated hip-hop events of the spring, catering to a dedicated fanbase that spans generations.
Primary Trust
Primary Trust begins its run at Crow’s Theatre on May 26, bringing a gentle and profound story to the East End. The play follows a man who has lived a very quiet, predictable life in a small town until a series of unexpected changes forces him to step out of his comfort zone, exploring themes of friendship, loneliness, and the courage it takes to start over at any age.
Fiddler on the Roof in Yiddish
Fiddler on the Roof in Yiddish premieres on May 28 at The Elgin Theatre, marking a landmark cultural event for the city. Directed by the legendary Joel Grey and starring Steven Skybell, this Harold Green Jewish Theatre Company production brings the beloved musical back to its cultural roots with English subtitles, offering a powerfully authentic and moving theatrical experience that has been celebrated internationally.
Kismet and Emma Bovary
Kismet and Emma Bovary premieres at the National Ballet of Canada on May 29, showcasing the technical brilliance of the company. This double bill features a world premiere by Jera Wolfe alongside Helen Pickett’s intense, dramatic adaptation of the Flaubert novel, offering a night of dance that ranges from fluid contemporary movement to the grand scale of classical drama.
Romeo Santos & Prince Royce
Romeo Santos & Prince Royce team up for the “Mejor Trade Que Nunca Tour” on May 29, bringing a massive night of Latin music to the city. The bachata icons will take over the Scotiabank Arena stage for a night of romantic rhythms and high-energy dance, combining their massive libraries of hits for a show that is sure to be a highlight for the local Latin community.
Martin Garrix
Martin Garrix closes out the month with a three-night residency at the RBC Amphitheatre starting May 29. His “Americas Tour” will transform the outdoor venue into a massive electronic dance party featuring state-of-the-art lighting, pyrotechnics, and the chart-topping tracks that have made him one of the biggest DJs in the world.
A$AP Rocky
A$AP Rocky concludes the month with his “Don’t Be Dumb World Tour” on May 31 at Scotiabank Arena. The rapper is known for his visually stunning, avant-garde stage designs and experimental sound, promising a cinematic and high-energy finale to the May concert schedule that bridges the worlds of music, fashion, and art.
IN THEATRES
The Devil Wears Prada 2
Meryl Streep and Anne Hathaway reunite on May 1 for a sequel that finds Miranda Priestly navigating a declining magazine industry while facing a professional rivalry with her former assistant, Emily Charlton. The film explores the clash between old-school prestige and the new guard of digital fashion media as the two women are forced into an unlikely alliance.
Animal Farm
Director Andy Serkis brings George Orwell’s political allegory to theatres on May 1 using cutting-edge performance-capture technology to modernize the tale for a 21st-century audience. This version features a voice cast led by Seth Rogen and Laverne Cox, reimagining the farm rebellion as a critique of how social media and technology can be used to consolidate power.
Mortal Kombat II
Mortal Kombat II hits theatres on May 8, continuing the brutal tournament between Earthrealm and Outworld with a cast that expands on the 2021 reboot. Directed by Simon McQuoid and starring Karl Urban as the charismatic Johnny Cage, the sequel promises even higher stakes, more elaborate fight choreography, and the signature “fatalities” that have made the game franchise an enduring staple of pop culture.
The Sheep Detectives
Hugh Jackman stars in this quirky mystery-comedy, premiering on May 8, as a shepherd whose flock has become expert detectives by listening to him read crime novels aloud. When a mysterious incident occurs on the farm, the sheep take it upon themselves to solve the “whodunit,” proving to be more brilliant investigators than the humans.
In the Grey
In the Grey arrives in cinemas on May 15, featuring a powerhouse action cast including Henry Cavill and Jake Gyllenhaal. Directed by Guy Ritchie, the story follows a group of elite specialists tasked with recovering billions in stolen assets, delivering the director’s signature blend of stylized violence, non-linear storytelling, and sharp, fast-paced dialogue that keeps the audience on the edge of their seats.
I Love Boosters
Boots Riley directs this surrealist heist caper arriving on May 22, starring Keke Palmer and Demi Moore as members of a sophisticated ring of professional shoplifters. The story serves as a vibrant and high-energy critique of corporate greed as the “boosters” target a cutthroat fashion mogul in an alternate-reality San Francisco.
The Mandalorian and Grogu
The Mandalorian and Grogu opens on May 22, marking the first time the beloved Star Wars duo moves from the streaming screen to a global theatrical blockbuster event. Directed by Jon Favreau, the film is an epic-scale adventure that sees the pair facing a new, formidable threat in the outer reaches of the galaxy, promising the kind of visual spectacle and emotional resonance that only the big screen can provide.
Tuner
Tuner premieres on May 29, a gritty and atmospheric drama starring Leo Woodall as a talented piano tuner with an extraordinary ear. The plot follows him as he gets pulled into the dangerous world of high-end safe-cracking, where his specialized hearing makes him the perfect criminal asset, forcing him to choose between his quiet craft and the allure of a life of crime.
NEW MUSIC
Kacey Musgraves – Middle of Nowhere
Following the success of Deeper Well, Musgraves returns on May 1 with her seventh studio album, a project that is expected to lean further into her signature blend of cosmic country and introspective folk-pop. The album, released via Lost Highway Records, continues her streak of deeply personal storytelling, focusing on themes of isolation and self-discovery in a world that feels increasingly disconnected.
The Black Keys – Peaches!
The Black Keys deliver their fourteenth studio album on May 1, which has been described as their most “natural” sounding project since their 2002 debut. Billed as a return to their raw blues-rock roots, the album features a collection of covers and original tracks that capture the gritty, unpolished energy that first made them icons of the indie-rock scene.
MUNA – Dancing on the Wall
The acclaimed trio returns on May 8 with an anthemic new record that doubles down on the synth-pop excellence and queer joy that defined their self-titled breakout. This project is being hailed as a definitive summer soundtrack, featuring high-energy production and the kind of emotionally resonant lyrics that have made them a staple for fans of indie-pop.
Punk rock veterans Social Distortion break a long studio hiatus on May 8 with a raw, hard-hitting collection that remains fiercely loyal to their Southern California punk and rockabilly heritage. The new tracks explore the grit of survival and the passage of time, delivered with Mike Ness’s unmistakable gravelly vocals and the band’s signature high-distortion guitar riffs.
NMIXX – Heavy Serenade
The JYP Entertainment girl group continues their “MIXX-pop” experimentation with their fifth mini-album, arriving on May 11 with a mix of romantic visuals and genre-bending soundscapes. Following the lead of their pre-release tracks “Superior” and “Crescendo,” the group is set to showcase their vocal versatility through a narrative that balances high-energy choreography with a more sentimental, cinematic atmosphere.
Gracie Abrams – Hit the Wall
Kicking off a brand-new musical era, Gracie Abrams releases her highly anticipated lead single on May 14 at 5:00 PM PST. The track is described by the Grammy nominee as a deeply personal creative evolution, featuring moody, evocative production and intimate lyrics that set the stage for her upcoming third studio album.
Drake -Ice Man
Toronto superstar Drake returns on May 15 with his ninth solo studio album, a project he famously teased by hiding the release date inside a massive ice sculpture in downtown Toronto. Featuring the singles “What Did I Miss?” and “Which One” with Central Cee, the album marks a return to his atmospheric, rap-heavy roots and serves as his first full-length solo effort since 2023’s For All the Dogs.
Maisie Peters – Florescence
Following her first UK No. 1 album, Maisie Peters returns on May 15 with a new body of work that continues her reign as a master of witty, relatable pop songwriting. Florescence is expected to showcase a more mature and reflective side of the artist, exploring the complexities of young adulthood with her trademark lyrical sharp-edged charm.
Bleachers – everyone for ten minutes
Jack Antonoff’s latest project under the Bleachers moniker arrives on May 22, offering a frenetic yet heartfelt exploration of modern life through an 80s-inspired rock lens. The album is described as a high-speed journey through nostalgia and anxiety, featuring the maximalist production and anthemic choruses that have become Antonoff’s stylistic calling card.
Paul McCartney – The Boys of Dungeon Lane
The legendary Beatle releases his twenty-first solo studio album on May 29, a nostalgic collection co-produced by Andrew Watt that draws inspiration from his childhood in Speke, Liverpool. Featuring the lead single “Days We Left Behind” and a confirmed collaboration with Ringo Starr, the album sees McCartney playing the majority of the instruments himself in a poignant return to his melodic roots.
Violet Grohl – Be Sweet to Me
Establishing her own musical identity, Violet Grohl makes her highly anticipated full-length debut on May 29 with a sound that expertly blends alt-rock edge with soulful, mature vocals. Having already shared the stage with her father, Dave Grohl, this solo project marks her official arrival as a formidable new voice in the alternative music scene.
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