I know a thing or two about having strong opinions on what is being transmitted into my living room – after all, I’m a born-and-bred American who grew up watching my dad shout at the Super Bowl. The Oscars is my Super Bowl: they are both glitzy, overlong American broadcasts featuring endless spectacle and distraction, beaming over to British TV at unsociable late-night hours and leading people to swear at their screens.
Sure: there have been some brilliant Best Picture winners: From Here to Eternity (1954), All About Eve (1951), Titanic (1998), Moonlight (2017), Oppenheimer (2024). This year, for my money, that Best Picture greatness contender is The Brutalist. But the Academy is an institution you can almost rely on to make weird decisions – this year’s nomination of the appalling, near-unwatchable Emilia Perez among them.
So today I’m here to round up seven of the worst offenders, outrages, and flat-out weird winners ever to grace (?) the Oscars stage. Get ready for some shouting.
Sweeping up Best Picture over Steven Spielberg’s Saving Private Ryan – and winning Gwyneth Paltrow a Best Actress statuette in the process – Shakespeare in Love remains one of the most notable Oscar controversies of modern day. Heavily fêted and pushed by its now-disgraced Miramax producer Harvey Weinstein, the fun but flimsy imagining of William Shakespeare’s love life into a plot-heavy romantic comedy, borrowing from several of his own plays, paled in comparison to the others nominated that year (including, for the record, another amazing war film, Terrence Malick’s The Thin Red Line).
Often used as evidence of how awards campaigning poisoned the Academy, and certainly not helped in retrospect by Weinstein’s convictions, it’s a film that hardly holds up strongly against a list of Best Picture winners. In 2015 The Hollywood Reporter ran a survey of Academy voters in the interest of doing a “recount” of several controversial wins. The vast majority said they’d have chosen Saving Private Ryan over Shakespeare in Love.
How many people of a younger generation – or in fact, any generation – hanker for a rewatch of Kevin Costner’s well-intentioned but corny Western? Can anyone you know quote every line from Dances with Wolves? Do people still talk about its bravura scenes – complicated tracking shots, needle drops, character deaths, or darkly comic scenes? Right. Now please compare and contrast to the modern classic that is Martin Scorsese’s Goodfellas, which has all of the above going for it and lost out to Dances With Wolves.
The Academy seemed to want to go for a film that addressed the chequered history of Native American and indigenous people – but they picked one directed by and centring on a white man that is little more than a plodding vanity project.
A notorious bum note in Oscar history and peculiar choice altogether, this backwards-looking white saviour movie was recognised, back in 1989 as well as in the present day, as being antiquated and borderline racist in its depiction of a subservient black driver (Morgan Freeman) who, through superhuman patience and understanding, shifts the bigoted attitudes of his old Jewish employer (Jessica Tandy). It’s all just a humiliating affair, frankly, particularly given how much the film seems to treat racism as an issue of the past – something we have largely “solved” as a society. What in god’s name were they thinking, when Spike Lee’s trenchant, powerful Do The Right Thing came out the same year and wasn’t even nominated?
One thing that the Oscars voting body has proven time and again is that it’s difficult to aggregate winners that will stand the test of time; there’s a long tradition of favouring what seems topical or en vogue. Because of this, it makes sense that Paul Haggis’s Crash would win over Brokeback Mountain, the then-controversial story of gay cowboy love from Ang Lee. Crash was, unfortunately, not just inferior to that film but just… not good.
The mish-mash of multiple stories in an apparent mosaic of various social ills across the city of Los Angeles is extraordinarily obvious and embarrassingly broad in its sketches of urban gang warfare and poverty – all from the point of view of a guy who based the film on the true story of his Porsche being carjacked. A shining example of what happens when you let a rich white guy try to show his bleeding-heart liberal credentials.
Once again revealing its conservative tendencies, the Academy’s top award went to the backward-looking ahistorical nostalgia of Gump over the tangy, violent postmodernism of Quentin Tarantino’s Pulp Fiction. I enjoy Gump as much as the next guy – who doesn’t love Tom Hanks? But the film’s underlying messaging is a cheap examination of social change that treats the anti-war movement as a joke, portrays hippies as mindless and insinuates that sexual promiscuity leads to tragedy. That’s before you get to the Aids crisis being used as a cheap plot device. It’s got plenty in the way of quotes but little to wrestle with beyond an enjoyable tale about a “simpleton”.
In a strong year for nominees, which included Alfonso Cuaron’s Roma and Yorgos Lanthimos’s The Favourite, it was a real head-scratcher that the Academy sprung for the already-controversial choice of Peter Farrelly’s Green Book, a kind of Miss Daisy in reverse wherein a racist white driver (Viggo Mortensen) drives a successful black pianist (Mahershala Ali) through the Deep South during the Jim Crow era. Perhaps voters felt fooled by the strength of the performances – these are two top-of-their-game talents – but the story itself is flimsy and looks to reconcile racial tension in an offensively saccharine way. This choice was all the more embarrassing for being made in 2019 – this film feels like it was made 20 years ago.
If the Oscars are experts in choosing winners that don’t age well, American Beauty feels like the pinnacle – or maybe the nadir – of that.
Starring the disgraced Kevin Spacey as Lester, a creepy suburban dad who becomes infatuated with his daughter’s high-school friend Angela (Mena Suvari), Sam Mendes’s film feels deeply uncomfortable to watch in 2025. Lester’s is a very Gen X malaise, too: no economic crisis, no Trump breathing down anyone’s necks, no real thought toward racial or sexual discrimination; this is a white man’s frustration with an otherwise very comfortable existence – today, all its efforts to be cool or subversive feel deeply cringeworthy.
Spacey’s deadpan voiceover tries to invoke modern middle-class life and the tediousness of “achieving” the American dream, but the objects of so much of his scorn are women. His wife Carolyn, played by the talented Annette Bening, is fobbed off and left clueless, whereas the camera ogles his teen crush Angela shamelessly. Not the kind of classic I’m keen to return to.
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