Oakdale Community Centre

I saw a lot of Toronto this year while working on a new guidebook, and few buildings surprised me like this one. Designed in the 1990s by Vancouver masters Patkau Architects with Toronto's Ralph Giannone, the building is a modest community centre and pool between unfancy suburban high-rises. Cheaply built, it's unmistakably a work of art, rich in forms, textures and ideas. Splashing with my kids and drying out on the sinuous concrete benches, I found an unexpected gift.

In/Future

The festival of art and music brought Toronto's modernist Ontario Place gloriously back to life, mashing up art and landscape, past and present. Max Dean's Still, which repurposed the kitschy figures and props of the site's log ride, was funny, poignant and eerie in the same moment.

Sharon Jones and the Dap-Kings at the Montreal Jazz Festival

On a hot August night, the soul singer connected with a big festival crowd, sending soulful vibes out into Place des Festivals and visibly growing stronger as the night went on. As she talked openly about her battle with cancer – and it was a battle; Jones was a fighter in every cell of her being – she seemed vulnerable and yet unstoppable. The end, three months later, came much too soon.

"Chile before Chile" at the Chilean Museum of Pre-Columbian Art

In a year when Canada stumbled (slowly) toward reconciliation with its aboriginal peoples, I was fascinated to find that Chile, a country of 17 million, has not one but two museums in its capital devoted to its pre-Columbian cultures. This ambitious and tightly curated museum brings together works from across the country and beyond in a grand colonial pile; an underground expansion by architect Smiljan Radic placed grand Mapuche grave markers in a wash of sunlight from above, retaining the gravity of their original purpose while adding a peculiar dignity.

Ellsworth Kelly at SFMOMA

The media preview for a new building is inevitably hectic, and my visit to the San Francisco Museum of Modern Art in April was no exception: I toured 170,000 square feet of new gallery space in a day and a half. Yet, for a few minutes, I had a room of Ellsworth Kellys entirely to myself, and the work of the artist – a painter whose output sometimes busts out into three dimensions – was full of revelations about colour, proportion, space and experience, things I couldn't have begun to understand without being there.

JOHN DOYLE

Dido and Aeneas by Opera Atelier, with the Tafelmusik Baroque Orchestra, at the Elgin Theatre

One goes to Opera Atelier to have everything extravagant – director Marshall Pynkoski and choreographer Jeannette Lajeunesse Zingg's gusto and fervid, imaginative Baroque operas. The music, the song, the dancing, the rococo ornamentation. This Dido and Aeneas was different, a pared-down version that was a 90-minute stunner and Wallis Giunta's coiled, stricken Dido could rend you asunder. Her climactic rendition of Purcell's gorgeous "When I am laid in earth," Dido's Lament, was a hypnotic, soul-searing end and it stayed with you for endless days. Performance of the year, by a mile.

Salt-Water Moon at Factory Theatre

The true reimagining of a much-loved Canadian classic is no easy task. Ravi Jain's charged, lean production of David French's great play was that – an eye-opener and deeply moving on two levels. First, the guts of the love story in the play itself were illuminated and, second, the powerful simplicity of the production, all bare stage and candles, was transporting. This was Salt-Water Moon denuded of Newfoundland sentimentality and adolescent aching. Mayko Nguyen as Mary Snow and Kawa Ada as her old sweetheart Jacob Mercer were lively, companionable and understated players as if they, like the audience, were wide-eyed at discovering the story for the first time. This version of the play was the familiar made instantly magical.

The Waking Comes Late by Steven Heighton

Heighton's collection of poems, which deservedly won a Governor General's Award, was at first a perplexing read. The poems are by turns angry, elegiac or simply intoxicated with wordplay and the intricacy of assonance. But they are richly rewarding on repeated reading. The unity of the collection is anchored in the author's age – the writer reflecting on struggles to overcome setbacks and coming to terms with the endless failings in human nature. It's a mature poet's work, its heft a growing feeling of assurance that's intimated in the loose, confident translations he includes of works by other poets.

Kevin Quain at Graffiti's in Kensington Market, Toronto

For some years, Kevin Quain, our most reclusive and one of our greatest songwriters, has been deprived of a regular showcase, since the Cameron House ceased his weekly Sunday night performances with his loose band the Mad Bastards. A chance to see him perform, with the spotlight solely on his gorgeously crafted, melancholy songs, is rare. Each chance is, however, a sterling reminder of his enormous skill in observing the urban bohemian life – songs of regret, loneliness and wry acknowledgment that, sometimes, hard-luck stories are the best. His work used to be called "garage jazz cabaret" but, these days, the elusive Quain's songs seem to emerge after long, long steeping in pensive contemplation of all our ordinary flaws and foibles.

A Little Too Cozy by Against the Grain Theatre Company, at the CBC Broadcasting Centre in Toronto

The energetic, innovative young opera company Against the Grain did it again. A Little Too Cozy was a fabulously ingenious rejigging of Mozart's Cosi fan tutte, set as a reality TV show, and performed in a TV studio to boot. The version drew out the core of the opera and still made it strikingly contemporary, with Twitter hashtags and audience social media engagement encouraged. Yet nothing about Mozart's work was trivialized in Joel Ivany and Topher Mokrzewski's version. The verve of the performers was joyous, with Cairan Ryan especially good as the icky TV host "Don L. Fonzo" and Caitlin Wood's Despina was a scene-stealer. A risk-taking production that soared to victory.

ROBERT EVERETT-GREEN

The Visitors

Icelandic artist Ragnar Kjartansson's joyous yet heartbreaking one-hour music video was the show-stopper at his Musée d'art contemporain retrospective in Montreal. People practically camped out in the big gallery where nine immersive video screens relayed a rambling transcendent performance from many rooms of a shabby-genteel mansion. The only problem with this piece was that it had to end.

Do Not Say We Have Nothing by Madeleine Thien

Thien's multigenerational novel traces the interwoven fates of several Chinese musicians whose work and aspirations are crushed by the continuing official needs of the Communist revolution. Historical events are no mere backdrop, but a driving force within this haunting account of the need to escape the traumas of the past without allowing them to be forgotten.

Pierre Lassonde Pavilion, Quebec City

The latest addition to the Musée national des beaux-arts du Québec brings a luminous modernity to a suite of diverse buildings that include a Beaux-Arts temple of art and a converted prison. The new pavilion's airy presence and the museum's sensitive installation of works from Quebec and beyond make this new OMA/Provencher Roy showplace on Quebec City's Grand Allée a must-see.

Cult Following by Little Scream

Laurel Sprengelmeyer's expansive second album as Little Scream finds the common threads between religious devotion and what happens when we fall in love, without ever mentioning a higher power directly. This transplanted Montrealer's songs are tragicomic and cinematic, and her sense of musical form and drama can surprise even on the umpteenth hearing. A stunningly ambitious and satisfying disc.

Ventriloquists Convention

This play, which ran at Montreal's Festival TransAmériques last spring, had the clammy intrusive feel of a Christopher Guest mockumentary, with most of the humour cut out and lots of personal horror put in. Playwright Dennis Cooper's improv-based script and Gisèle Vienne's fearless direction helped make this Puppentheater Halle show an unforgettable masterclass in the art of blurring the line between fictional narrative and personal catharsis.

Barry Hertz

Atlanta

With his FX series Atlanta, Donald Glover has created something wholly original and thrilling – a vision of a world barely glimpsed in mainstream media, and one torqued to Glover's uniquely surrealistic sensibilities. (The show's many charms include a world where Justin Bieber is black, and rappers drive invisible sports cars.) If that weren't enough, Glover has crafted Atlanta's best episodes not around his own character – a perpetually broke hip-hop promoter – but wonderful supporting players, such as Zazie Beetz, and the brilliantly deadpan Brian Tyree Henry.

The Hamilton Mixtape

Last year, I was bemoaning the fact that I'd likely never be able to watch Lin-Manuel Miranda's Broadway juggernaut in person. Now, I'm twisting over the fact that no one (barring some sort of miraculous charity performance?) will be able to walk into a theatre and watch such diverse talents as Ja Rule, Queen Latifah, Riz Ahmed and K'naan perform their remixed versions of Hamilton's show-stoppers. But at least Miranda's mixtape, which collects those performances, is an excellent consolation prize.

How to Survive a Plague by David France

Although it was lost amid coverage of Donald Trump's electoral victory, the Nov. 14 issue of New York Magazine contained one of the year's most remarkable pieces of journalism: an excerpt from David France's How to Survive a Plague. After rushing through it, I turned to the mammoth work itself, which expertly traces the AIDS epidemic that would come to sweep New York City, with France on its front-lines as 100,000 people died of the disease. Heartbreaking, astounding, and a call to action even today, the book is the must-read of the year.

"That scene" from Sausage Party

If you have seen, and survived, Seth Rogen and Evan Goldberg's cinematic equivalent to lunatics running the asylum, then you already know which scene I'm talking about. If you have not yet witnessed it, then lock the doors, shut the blinds, and gird yourself for the most delightfully delirious seven minutes of your year.

Come from Away

I walked into this musical with a healthy dose of city-slicker cynicism: Could I really sit through a musical pivoting around the kindness of the Gander, Nfld., townspeople who sheltered stranded airline passengers in the aftermath of 9/11? It turns out: hell yes, and pass the screech.

SIMON HOUPT

Letterkenny

Bonkers, loopy, impressively filthy fun. Born as a Web series of shorts in 2013, the six-episode first season, which streams on CraveTV, brings us the everyday problems of farm hicks Wayne (series co-creator Jared Keeso), his sister Katy (Michelle Mylett), and best friend Daryl (Nathan Dales). The rapid-fire dialogue is hilarious and gross, and you won't catch near half it on the first go round. But sure as God's got sandals, this deserves to be a big hit.

Four in the Morning

When did CBC comedy get so grown-up – and so inspired? This summertime series (which you can stream on the CBC app) aired at 9 p.m. on Fridays, which is a little stunning, considering its adult language and material. Four twentysomething friends roam the streets of Toronto after midnight, struggling with love and career and whether to blow up the moon. Inspired, offbeat, and a surreal, delirious delight.

Arrival

Montreal director Denis Villeneuve's best English-language work so far is a luminous, cerebral meditation on language and the primal, primary role of narrative in our lives. (It could be called Stories We Tell.) An alien visitation thriller that's only glancingly about aliens, it will leave you emotionally racked and yet never more alive.

A Chorus Line

It's hard for audiences to go wrong when they submit to the deep pleasures of whatever musical thrills the Stratford Festival whips up each summer with director Donna Feore, but this year's A Chorus Line – the first authorized reimagining of the show since its off-Broadway debut in 1975 – was exhilarating, from the opening number to the chorus-line high kick finale of 26 dancers stretched across a suddenly glittering stage: unique and heartbreaking individuals transforming themselves into one singular sensation.

Pneuma

Toronto's annual dusk-to-dawn art bacchanal known as Nuit Blanche is a thrill, but sometimes its pleasures are best encountered free of the madding crowds, when some pieces stick around a few extra days. And so, one evening in early October, I stumbled upon Floria Sigismondi's trippy installation in the pool at Toronto's Nathan Phillips Square, a dreamlike 7-1/2-minute film (with a spectral Boards of Canada soundtrack) that, projected against a horizontal wall of water, seemed to take on three dimensions. It took days to shake fully free of its trance.

MARSHA LEDERMAN

The Tragically Hip, Vancouver

Some in the Vancouver audience were already in tears when Gord Downie walked onstage in his shiny suit. It was the second date of the Tragically Hip's Man Machine Poem Tour and while the band wasn't calling it their final tour, that's how it felt, given the news of Downie's brain cancer. The whole night was electric, but Grace, Too was especially rich – fabulously, yes. Notebook in hand, I wept with the crowd, too.

Betroffenheit

A slowly snaking mess of cables opens this stunning hybrid of theatre and dance, co-created by choreographer Crystal Pite and playwright Jonathon Young, who stars as a man lost and nearly consumed by grief. Dark, gorgeous and sublimely imaginative, the work is based on an unimaginable, real-life tragedy – the death of Young's daughter and her two cousins in a fire. Here the greatest grief is channelled into great art – devastating and powerful.

Onegin, Arts Club Theatre Company

"An insult! Leads to a challenge! Leads to a duel!" I can still hear this chant in my head, months after seeing Amiel Gladstone and Veda Hille's spectacular original musical, adapted from the Pushkin poem and Tchaikovsky opera. The show featured an outstanding ensemble cast (including real-life partners Meg Roe and Alessandro Juliani), an onstage band, a thrust stage bordered by stacks of books, and costumes to die for.

Better Things

Why aren't more people talking about this fantastic FX series? Pamela Adlon, who co-created the show with Louis C.K., stars as Sam Fox, a single mother of three daughters. A Hollywood actor, voice-over artist and former child star, Sam is a stressed-out, sexy, multitasking mom who teaches life lessons at the dinner table and – in possibly the season's best scene – a department store fitting room. Strong and flawed, she is the friend we all want, the mother we might all want to be.

Christine

Rebecca Hall is fantastic as Christine Chubbuck, the 29-year-old American news reporter who killed herself during a live TV broadcast in 1974. Under Antonio Campos's direction, Hall plays the tragic eponymous character as a serious, ambitious journalist who is too socially awkward (and principled) to pull off the human interest fluff pieces that are demanded of her. As Christine slowly comes undone, you know what's coming – but can't take your eyes off the screen.

MARK MEDLEY

Stranger Things

If a group of TV executives had subjected me to weeks of focus groups, hired a detective to conduct extensive research into my childhood, and placed probes on my skull to monitor my dreams at night, they still wouldn't have come up with a show so perfectly me. Yes, this Netflix series, a frightening and affecting coming-of-age story about three geeks searching for a missing friend, and a strange girl with otherworldly abilities, sometimes seems like someone's lost home movies from the eighties – Dungeons & Dragons! Walkie-talkies! BMX bikes! – but it's also a beautifully crafted treatise on the childhood bonds that build our lives. There's a part of me that wishes it wasn't coming back for a second season, but I'll be binge-watching it along with everyone else.

Reply All

This podcast, which looks at the intersection of technology, culture, current events and, above all, the Internet, premiered in late 2014 but I only began listening to it at the start of the year. I'm slowly listening to all the old episodes, because I don't want to miss a thing: Hosts PJ Vogt and Alex Goldman are producing some of the best journalism, on any platform and in any medium, you'll find today. If you're new to the series and don't know where to start, I suggest Boy in Photo (about a viral photograph), Stolen Valor (an investigation of military imposters), and Zardulu (a look at rats in New York).

American Crime Story: The People vs. O.J. Simpson

After giving up on both Glee and American Horror Story after their respective first seasons, I thought I was done with Ryan Murphy. But his new anthology series, each season of which will dramatize a flash point in American legal history, was among the most arresting (groan) things on TV this year. The show is anchored by career-making performances by Sarah Paulson, Courtney B. Vance, and above all, Sterling K. Brown.

Good Advice by Basia Bulat

This Montreal-based singer-songwriter has been a personal fave since her debut, Oh My Darling, in 2007. Her fourth LP, written in heartbreak and recorded down in Louisville, Ky., didn't resonate with me as immediately as her previous albums; instead, its 10 songs burrowed themselves deeper into my brain as the year stretched on. It's a testament to her skill and progression as a songwriter, which grows with each effort.

Ali Wong: Baby Cobra

Thanks to Netflix, I'm watching way more stand-up comedy than I ever have before. Nothing else I watched this year approached the heights of Baby Cobra, which is Wong's first special, hard as it is to believe. Wong, who's also an actress and screenwriter, delivers a blistering, side-splitting, extremely vulgar and incredibly smart set that dives into all the old standbys – sex, money, gender, ethnicity – but makes them her own.

J. KELLY NESTRUCK

The Idea of North: The Paintings of Lawren Harris, Art Gallery of Ontario

An astonishing exhibition curated, yes, by Steve Martin, but also Andrew Hunter – who augmented and expanded it brilliantly for Toronto. It allowed me to marvel at Harris's metaphysical landscapes anew, and fully understand the problematic nature of his (and the Group of Seven's) desire to paint an idealized, human-free Canada. The show doubled as a history of the demolished Toronto district, The Ward – Anique Jordan's photos, imagining the black people and places unpainted by Harris in the area, were particularly memorable.

The People v O.J. Simpson: American Crime Story

I was just a teenager when the O.J. Simpson trial took place – and, while I remembered the media frenzy, I had hardly any understanding of what a complicated intersection of race and sexual politics it comprised until watching this FX miniseries. Entertaining but not exploitative, it featured performances that were a mix of the truly brilliant and enjoyable off-kilter. The chemistry between Sarah Paulson and Sterling K. Brown as prosecutors Marcia Clark and Christopher Darden was the sexiest thing I've seen on TV in a long time.

Arrival

This is the kind of smart sci-fi film I hadn't realized I'd been missing. Director Denis Villeneuve's slow-burn alien-encounter drama catapulted him back to the top of my list of favourite filmmakers – with Amy Adams's understated performance and that twist ending making me weep more than I have at a movie since, well, maybe Villeneuve's 2009 film, Polytechnique.

Lemonade by Beyoncé

If Americans are just going to vote celebrities in as presidents from now on, the Democrats should run Beyoncé in 2020. This year, she channelled anger not into destructive or hateful politics, but into great art – and then brought it to red staters at the Super Bowl and the Country Music Association Awards. Personal, political, Lemonade was a true album with a satisfying, hopeful emotional arc – and not one skippable track.

The Tragically Hip, Kingston

The Hip performed one last song, as part of a third encore, for the final time. "No dress rehearsal – this is our life," Gord Downie sang in Kingston. I sang along with strangers at a bar in Toronto. I looked at my phone and saw this Ahead By a Century lyric tweeted from coast to coast. What an extraordinary, exceptional event in this vast land afraid to know itself – a third of us singing along together.

KATE TAYLOR

Luminato

The 2016 edition of Luminato was launched in June by a group of BASE jumpers throwing themselves off the smokestack of the decommissioned Hearn Generating Station in Toronto's port lands but it was the interior of the abandoned industrial space that really proved breathtaking. Whether illuminated by a giant disco ball or filled with the sounds of electronic music, the Hearn emerged as a weird and wonderful cathedral of concrete, rust and grime.

Sophie La Rosière

Who is Sophie La Rosière anyway? At the Art Gallery of York University in September, a reconstruction of her studio revealed an early-20th-century French painter of golden flowers and baroque vulvae hidden away beneath coats of black paint as though the mysterious artist wanted to erase her own talent. More intriguing still was the realization that this compelling anti-autobiography is entirely invented; La Rosière is a fictional character created by contemporary artist Iris Haussler.

12 Angry Men, Soulpepper

On stage in Toronto in January, Soulpepper's production of 12 Angry Men proved that the classic courtroom drama still has the power to shock and amaze – especially if you watch it from the perspective of a gobsmacked 12-year-old who is comparing the gripping live theatre experience with an old movie he once watched.

Marni Jackson's reading at the Kingston Writers Festival

An invitation to read their fiction to the accompaniment of improvised jazz would be a daunting assignment for most writers, but at the Kingston Writers Festival in October, Marni Jackson showed the literati how it should be done. She effortlessly matched the music with a hilarious riff on celebrity – a picnic with Leonard Cohen, Taylor Swift and Karl Ove Knausgaard – plucked from her first novel, Don't I Know You.

Francis Alys, AGO

To create his 20-minute film Reel/Unreel, the Belgian-Mexican artist Francis Alys shot boys unspooling film reels through the streets of Kabul the same way they might roll their hoops. The piece, a life- and art-affirming retort to the Taliban's attempt to destroy the Afghan film archive, is spectacularly projected onto a large screen in a vast room at the Art Gallery of Ontario through March, 2017.

BRAD WHEELER

Lawren Harris's Mountain Forms sells for a record $11.21-million

"One quick crack of the hammer, and one giant leap for the Canadian art market," said the auctioneer, when the circa 1926 landscape obliterated the previous record price for a Canadian painting sold at auction. A packed house applauded. With the sale of Mountain Forms, Canadiana had reached an unforeseen peak.

Based on a True Story: A Memoir by Norm Macdonald

It is ironic that the Canadian comedian Norm Macdonald was let go from Saturday Night Live for saying something that many believed to be true – that O.J. Simpson was a murderer – and that his critical-hit "memoir" is a big, fat, lovely lie. Based on a True Story is a fantastical yarn that is ambitious in form, gonzo in imagination and hallucinogenic in its facts. Note to self: Macdonald can write.

Jean-Michel Blais

One early evening in April, a minimalist pianist was unveiled in the atrium of the Art Gallery of Ontario. Montreal's Jean-Michel Blais, an unknown at the time, played pop melodies and presented his classically trained form. As he performed, sketch artists rubbed paper with charcoal and one woman – mouth open, hand to chest – was in awe of the unpretentious musician's art. At the gallery, this was a painting in sublime sound and motion.

Saturday Night Live's Black Jeopardy skit

When playing Jeopardy!, contestants are reminded to phrase their answers in the form of a question. With that in mind, what comedy sketch best addressed class and race in America in 2016? The actor Tom Hanks played blue-collar Doug, whose disempowerment and suspicion of authority were shared by his black competitors. Racial lines were blurred as a sort of unity was suggested. I'll take sneakily sophisticated satire for $500, please.

Corin Raymond's merchandise moment

I'm at the bar at Toronto's Cameron House, sitting next to the Canadian balladeer Corin Raymond, when an artisan arrives to deliver a prototype of the cherry-wood beer steins that would be sold to raise funds for Raymond's latest album Hobo Jungle Fever Dreams. The troubadour has a Christmas-morning grin as he clutches and hugs the stein as if it were the Holy Grail. And maybe it is. In a world where things are easily disposed, Raymond's devotedness to song and other things built to last is priceless.