It’s a truth universally accepted that the Oscars doesn’t always (or even often) get it right. While there are some truly head-scratching victors among the ranks of Academy Award winners, it’s also true that Oscar often likes to play catch-up, rewarding filmmakers and actors for late-career work when they probably should have won for something else years or decades back.
Take Angela Bassett, up for Best Supporting Actress for her performance in Black Panther: Wakanda Forever. If she wins, will it be because she truly gave a career-best performance in the Marvel movie? Or will it be, at least in part, a means of making it up to an actress who should’ve won one already? Academy voters sometimes take a long time to see the talent that’s right in front of their faces. And not every classic is recognized immediately.
Oscar history is filled with examples of actors, actresses, and other filmmakers who won the right prize for the wrong movie. Some of these are close decisions; perhaps the film or performance they won for was good, but as good as another in their filmography. And then there are the times people won awards for middling, forgotten movies while indelible work in classic films went ignored.
Judi Dench
Won for: Shakespeare in Love
Should’ve won for: Iris (2001)
Shakespeare in Love is a wonderful movie, and a rare, relatively recent instance of Academy valuing a smart, frothy comedy over something more overtly epic. Judi Dench makes an impression in her few minutes of screen time, as she always does, but in a career of subtle, nuanced performances, it hardly feels like her biggest challenge. There are several other roles that run deeper for the actress (including her portrayal of M in Skyfall), but her performance as author Iris Murdoch, struggling through the stages of Alzheimer’s, 2001's Iris is a real showcase for her talents. Dench plays both strength and vulnerability with equal power, and her energy and spirit ensure that the film never feels needlessly maudlin or by-the-numbers.
Where to stream Shakespeare in Love: The Roku Channel, Fubo
Where to stream Iris: Digital rental
Al Pacino
Won for: Scent of a Woman
Should’ve won for: The Godfather, Part II
Though he received several nominations, Al Pacino’s 1970s golden age didn’t reward him with any actual Oscars. It wasn’t until 1992, and his performance in the all-but-forgotten Scent of a Woman, that the Academy finally recognized Pacino. It’s a fine performance that carries the movie, but by 1993, we were already well on our way to the excessively shouty Pacino we know today. His performance in Heat two years later was better, but his quiet descent in The Godfather, Part II is one of the greatest in American film history.
Where to stream Scent of a Woman: Prime Video
Where to stream The Godfather, Part II: Peacock
Denzel Washington
Won for: Training Day
Should’ve won for: Malcolm X
Al Pacino won Best Actor for Scent of a Woman the same year Denzel Washington was up for his turn in Spike Lee’s characteristically unconventional biopic. Washington melts into the role of Malcolm X so fluidly and flawlessly that at times it’s easy to forget that we’re watching a dramatization and not footage from the activist’s life. His edgy performance in Training Day is certainly captivating, but it’s hard to see his win as anything but an Academy mea culpa.
Where to stream Training Day: HBO Max, Hulu
Where to stream Malcolm X: HBO Max, Tubi
Meryl Streep
Won for: The Iron Lady
Should’ve won for: The Devil Wears Prada
This was the actress’s third Oscar win out of 21 total nominations (so far), so it’s not like she needs a swap out, but I’d skip this award (for a fine performance in an OK movie) in favor of her role as fashion editor and queen bitch Miranda Priestly in The Devil Wears Prada. Priestly could’ve come off as a cardboard villain, but in Streep’s hands, the character takes on nuance and complexity without losing her sharp edges. It might have been impressive if Streep had made the character empathetic, but she does something better: She makes Priestly interesting.
Where to stream The Iron Lady: HBO Max, The Roku Channel
Where to stream The Devil Wears Prada: Tubi
Whoopi Goldberg
Won for: Ghost
Should’ve won for: The Color Purple
Ghost is great, really, but an impossibly young Whoopi Goldberg carried Spielberg’s depression-era epic just a half-decade prior, convincingly portraying the growing strength of an enslaved girl over years. There’s no comparison, really.
Where to stream Ghost: Digital rental
Where to stream The Color Purple: HBO Max, Tubi
Elizabeth Taylor
Won for: BUtterfield 8
Should’ve won for: Cat on a Hot Tin Roof
Even Liz Taylor kinda hated BUtterfield 8, a seamy sex worker melodrama whose only real draw is Taylor’s performance itself, which is hardly the best of her career; given that this was the fourth time she was nominated, it feels like a classic case of “let’s just give her an Oscar, any Oscar.” She won a more deserved award for Who’s Afraid of Virginia Woolf? a few years later, but her performance in Cat on a Hot Tin Roof a few years earlier is nearly as worthy. The screenplay muted some of the themes of the Tennessee Williams play, and Maggie’s histrionics might have easily overwhelmed all that was left. Instead Taylor plays it just right, giving a performance that’s appropriately showy but never stagey.
Where to stream BUtterfield 8: Digital rental
Where to stream Cat on a Hot Tin Roof: HBO Max
Julianne Moore
Won for: Still Alice
Should’ve won for: Far from Heaven
Moore’s performance in Still Alice, as a linguistics professor coping with an Alzheimer’s diagnosis, is Oscar-worthy in the sense that the Academy loves it when people play tragic figures, but the film itself occasionally veers into emotionally manipulative territory. But Far from Heaven, and Moore’s performance in it, are brilliantly subtle. To experience the full measure of her formidable talents as an actress, you can’t do better than this story of repressed longing.
Where to stream Still Alice: Netflix, Hulu
Where to stream Far from Heaven: Digital rental
Cate Blanchett
Won for: The Aviator
Should’ve won for: Carol
The Aviator is perfectly fine, but hardly at the top of Martin Scorsese’s filmography. Likewise, Cate Blanchett’s performance as Katherine Hepburn: it’s good, maybe even great, but it always feels like the impersonation it is, and the character’s range is limited. It’s all on the table in Carol, though, with Blanchett giving a subtle, nuanced, but powerful performance that helped win the film a ten-minute standing ovation at Cannes.
Where to stream The Aviator: Netflix
Where to stream Carol: Tubi, Redbox, Freevee, The Roku Channel, Hoopla, Vudu
Jessica Lange
Won for: Blue Sky
Should’ve won for: Frances
Langehas two Oscars: she won Supporting Actress for Tootsie and Best Actress for Blue Sky. They’re both reasonable choices, though her turn in Tootsie doesn’t make full use of her talents, while Blue Sky sees her give a fine performance in film that was already largely forgotten by the time the ceremony rolled around. It’s Frances, though, a biopic dealing with troubled, groundbreaking 1930s-era actress Frances Farmer, where Lange really shows what she’s capable of. As written, the movie is excessively sordid, but Lange pours heart and soul into her performance.
Where to stream Blue Sky: The Roku Channel, Tubi, Pluto, Hoopla
Where to stream Frances: Digital rental
Kate Winslet
Won for: The Reader
Should’ve won for: Eternal Sunshine of the Spotless Mind
The little-seen The Reader is good, even if it feels like medicine. I’d suspect that part of Winslet’s win here, out of a career chock-full of brilliant performances, has a lot to do with some of the boxes it ticks—things that the Academy traditionally loved to reward; it’s a Holocaust drama in which Winslet’s character requires various prosthetics. If we had to give her just one career award, there are better choices; her zany turn in Eternal Sunshine of the Spotless Mind transforms a character who could’ve come off an another manic pixie dreamgirl into the true heart of that film.
Where to stream The Reader: Fubo, The Roku Channel, Kanopy
Where to stream Eternal Sunshine of the Spotless Mind: Prime Video
Paul Newman
Won for: The Color of Money
Should’ve won for: The Hustler
Martin Scorsese’s decades-later sequel to The Hustler is an unsentimental triumph, but it’s not quite the movie the original is. A sordid, complex tale of attempted redemption, everyone in the legendary cast (Newman, Jackie Gleason, Piper Laurie, George C. Scott) is at the absolute top of their game, and the resulting chemistry elevates each of them, none less that Newman, who should’ve won the first time around.
Where to stream The Color of Money: Digital rental
Where to stream The Hustler: IndieFlix, or digital rental
Sandra Bullock
Won for: The Blind Side
Should’ve won for: Gravity
The Blind Side, legitimate white savior narrative concerns aside, is a fairly conventional sports drama in the uplifting vein, one in which Bullock happens to give a pretty good performance. In Alfonso Cuarón’s Gravity, though, she carries the entire movie—it’s virtually a one-woman show that would’ve sunk dismally with a less compelling lead performance.
Where to stream The Blind Side: TBS, TruTV
Where to stream Gravity: HBO Max
Alfonso Cuarón
Won for: Roma
Should’ve won for: Children of Men
OK, Gravity might be Sandra Bullock’s best single performance, but it’s not director Alfonso Cuarón’s best film—though it is a stunning technical achievement, so we’ll let him keep it. But he also won for 2019's Roma, which is gorgeous, I’d rather have seen him awarded for Children of Men: not only is the film a complex story of faith and futility that only gets more relevant with age (and as our world grows increasingly existentially awful), it’s also a technical marvel on a level with Gravity, full of impressive and complicated single take sequences (or at least, scenes that appear to be single takes) and seamlessly integrated special effects that serve the plot without being intrusive.
Where to stream Gravity: HBO Max
Where to stream Children of Men: Digital rental
Carol Reed
Won for: Oliver!
Should’ve won for: The Third Man
Oliver is fine as stage-to-screen adaptations go, but slight when it’s not being overlong, not really even cracking the top five in director Carol Reed’s filmography. On the other hand, the seedy, cynical The Third Man is not only one of his best movies, it’s one of the best movies ever made—a twisty, masterful, morally complex noir that delivers juicy performances and is strikingly beautiful in its expressionist influences.
Where to stream Oliver!: HBO Max
Where to stream The Third Man: The Criterion Channel
Robert Zemeckis
Won for: Forrest Gump
Should’ve won for: Back to the Future
Look, I know that people love Forrest Gump—apparently alongside Titanic, it’s the Oscar winning the general public loves best—but Back to the Future is a much more impressive achievement. A technically flawless crowd-pleaser that does everything right while managing to look like a light sci-fi comedy.
Where to stream Forrest Gump: Netflix
Where to stream Back to the Future: Peacock
Bette Davis
Won for: Dangerous
Should’ve won for: All About Eve
Even though it’s not her best work, we’ll let Bette Davis keep her Academy Award for Jezebel; it it’s a memorable performance and a bit out of her normal wheelhouse. Dangerous, though? It’s a mostly dull and sentimental melodrama—not terrible, but definitely not worthy of representing Davis’ entire career. All About Eve, on the other hand? One of our greatest motion pictures, with Davis saucily delivering one clever, whip-smart barb after another while also, amazingly, playing a human being.
Where to stream Dangerous: Digital rental
Where to stream All About Eve: Digital rental
Jack Lemmon
Won for: Save the Tiger
Should’ve won for: The Apartment
Even film buffs might be forgiven for never having heard of Save the Tiger, the meandering story of a morally conflicted furniture business owner. It almost works as a story of the failures of the American dream in the ‘70s, but never really adds up to much. The Apartment, however, is one of the great American movies of the 1960s, a comedy that’s deeply cynical until it offers up some hard-won hope in the final act. Without Lemmon’s performance as a meek but ambitious insurance clerk, the movie just wouldn’t work.
Where to stream Save the Tiger: Kanopy, Pluto
Where to stream The Apartment: Paramount+, Tubi, The Roku Channel, Freevee
Morgan Freeman
Won for: Million Dollar Baby
Should’ve won for: The Shawshank Redemption
No one paid much attention to Shawshank when it was released in 1994: it did only OK box office, and won zero of the seven Oscars it was up for (including a Best Actor nomination for Freeman). He should have won; Million Dollar Baby is good, but Shawshank is indelible, and likely the role that he’ll be most remembered for.
Where to stream Million Dollar Baby: HBO Max
Where to stream The Shawshank Redemption: HBO Max