No matter who or what wins on Oscar night on Sunday, there are sure to be dissenters. Not everyone was thrilled last year, for instance, when Emma Stone beat out favourite Lily Gladstone for best actress. In that spirit, here are some Academy Awards snubs, listed chronologically, that our staffers still can’t shake and one — maybe — still to come.
1999
Worst win: “Shakespeare in Love,” best picture
Why it’s so terrible: I generally have nothing against rom-coms set in olden times, but this trifle about a broke, writer’s-blocked, philandering Shakespeare (Joseph Fiennes) finding inspiration in an affair with a cross-dressing noblewoman turned thespian (Gwyneth Paltrow) was up against not one but three critically acclaimed Second World War movies: “Saving Private Ryan,” “Life Is Beautiful” and “The Thin Red Line.”
What should have won: “Saving Private Ryan.” Steven Spielberg’s masterpiece is one of the greatest war films ever made, viscerally putting viewers in the midst of battle without glorifying it or downplaying its cost.
Debra Yeo, culture editor
2000
Worst win: Michael Caine, best supporting actor, “The Cider House Rules”
Why it’s so terrible: The Oscars have a long-standing tradition of doling out lifetime achievement awards to old faves for middling performances vs. celebrating the more electrifying roles they should have won for. One of the more egregious examples? Sweet ol’ Michael Caine winning his gold statue for a utilitarian performance in a pretty blah adaptation.
Who should have won: Tom Cruise in “Magnolia.” He exhibits max masc star power as loathsome pickup artist king T.J. Mackey, but two more vulnerable sequences should have snagged Mr. Movies the ultimate Hollywood prize: one where a TV interviewer breaks him down about his absent dad and one where he confronts the dying patriarch himself. A reminder that the man can really act.
Briony Smith, culture and lifestyle reporter
2015
Worst win: “Birdman or (The Unexpected Virtue of Ignorance),” best picture
Why it’s so terrible: Alejandro González Iñárritu’s dark comedy about a faded superhero actor who attempts to revive his career by writing, directing and starring in his own Broadway show is, like its spiralling central character (played by Michael Keaton), nothing short of a maniacal mess. “Birdman” was so dense, so ambiguous, so pretentious that it ended up saying nothing at all.
What should have won: “Boyhood,” Richard Linklater’s epically intimate masterpiece was filmed over 12 years and follows a young boy (Ellar Coltrane) growing up in suburban Texas. It was everything that “Birdman” was not: unpretentious, deceptively simple and with a rock-solid emotional core. It was, without a doubt, the best film of the season. That it was almost shut out of the Oscars (Patricia Arquette nabbed the film’s only golden statuette, for best supporting actress) was not only surprising, but incredibly disappointing.
Joshua Chong, culture reporter and arts critic
2016
Worst win: “Writing’s on the Wall” from “Spectre,” best original song
Why it’s so terrible: In 2016, singer-songwriter Anohni became the first trans performer ever nominated for an Oscar. And yet, despite this historic milestone, Anohni’s performance at the ceremony was cut due to “time constraints”; meanwhile, Dave Grohl, who was not nominated, was added to the show. The salt in the wound, of course, came on the evening of the ceremony, when Jimmy Napes and Sam Smith took home the statue for their boring-as-hell James Bond theme that sounded like every other song in that saturated microgenre: dull, melodramatic and utterly forgettable. (In 2021, Variety ranked it the worst Bond song of all time.)
What should have won: “Manta Ray” was written by Anohni and composer J. Ralph for “Racing Extinction,” a documentary that explores the ongoing anthropogenic mass extinction of species caused by climate change, human overpopulation and agriculture. A delicate piano ballad wreathed in cinematic strings, “Manta Ray’ is not only the most stunningly beautiful song nominated in the best original song category in 2016; it’s one of my favourite songs to ever appear in a film.
Richie Assaly, culture reporter
2018
Worst win: “The Shape of Water,” best picture
Why it’s so terrible: “The Shape of Water”’s victory wasn’t terrible due to the film itself, but rather the fact that it confoundingly beat out many far more impressive and memorable flicks. That year was chock full of outstanding films, from the epic “Dunkirk” to the tender, heartfelt “Lady Bird.” That said, “Shape” is hardly a treat; its esthetic is muddy and its characters are often one-dimensional and predictable.
What should have won: “Three Billboards Outside Ebbing, Missouri.” Invigorated by sensational performances from Frances McDormand and Sam Rockwell — who took home best actress and best supporting actor prizes, respectively — “Three Billboards” is well-paced and arresting.
Hayden Godfrey, staff reporter
2023
Worst win: “Everything Everywhere All at Once,” best picture
Why it’s so terrible: Within the first five minutes of this incoherent action-comedy-whatsit, I had completely checked out. The densely layered, anime-indebted multiverse and head-spinning ingenuity that captivated audiences worldwide, not to mention the motion picture academy, just had me reaching for some Gravol. How it manages to move so quickly yet remain so utterly boring is its true innovation.
What should have won: “Triangle of Sadness” is a similarly polarizing two-and-a-half-hour fun fest that told its out-there story coherently and with a novelistic richness. It also made me cackle like a macaque.
Doug Brod, culture editor
2025
Worst win: Anything by “The Brutalist”
Why it’s so terrible: A movie that pretends to be about architecture and the Holocaust that is really about nothing more than the director’s seemingly bottomless desire to win an Oscar. Like Toronto’s brutalist architecture, “The Brutalist” is more something that pretentious bores pretend to like than it is a work of convincing, let alone enjoyable, art.
What should win: Take your pick: “Anora,” “Dune: Part 2.” I could go on.
Richard Warnica, staff reporter
