Worst Oscar wins ever

The academy doesn't always get it right. In fact, a lot of times, they get it very, very wrong. Here are some of the most shameful wins in Oscar history.

Best Picture

“How Green Was My Valley” beats “Citizen Kane” : Orson Welles’ “Citizen Kane,” now considered by many to be the greatest film ever made, seemed to confound the academy when it was originally released.

Ahead of its time in so many ways, “Kane” lost to the more measured and traditional fare of John Ford’s “How Green Was My Valley” for what I assume was no other reason than a complete lack of foresight on the academy’s part. There was a history of animosity towards Welles from the academy, and while it was nominated for nine Oscars, the only award “Kane” took home was for Best Original Screenplay.

“Driving Miss Daisy” wins and “Do the Right Thing” isn’t even nominated: Sometimes the academy is so behind the times it’s jaw-dropping. In a year where probably the best film ever made about race relations in America — Spike Lee’s daringly button-pushing “Do the Right Thing” — was released to critical raves, Bruce Beresford’s aw-shucks tale of a black driver and his white boss nabbed the Best Picture honor.

It’s one of Morgan Freeman’s better performances, and there’s a neat little moral in the center, but the “Miss Daisy” take on race relations is the elementary school pop-up book counterpart to Spike Lee’s Master’s thesis.

“Shakespeare in Love” beats “Saving Private Ryan”: In my personal opinion, this is the worst decision and worst moment in Oscar history. Miramax flooded the academy with downright brown-nosing, sniveling appeals for “Shakespeare in Love” to win every award it possibly could.

The academy took the bait, even giving Judi Dench a Best Supporting Actress award for about five minutes of screen time. Steven Spielberg, one of those non-ambitious “let the movie campaign for itself” types, took home the Best Director prize for “Saving Private Ryan,” his second World War II masterwork in a row, but lost out to “Shakespeare” for Best Picture for no other reason than the Weinstein brothers spit-shined academy voters’ shoes and sent them expensive bottles of liquor. This is the one travesty that the academy will never live down.

“Crash” beats “Brokeback Mountain”: Hollywood is a town that is generally friendly to the homosexual community, so when Ang Lee’s excellent tale of two male ranch-hands in love was the favorite for Best Picture going into Oscar night, it was assumed to be the automatic winner. Not so.

Paul Haggis’ tone-deaf lecture on modern race relations, “Crash,” upset the apple cart and stole Best Picture right from under Ang Lee’s nose. Some suspected bigoted academy voters shunned “Brokeback” for its onscreen depictions of gay sex and men kissing. Others thought it was Hollywood trying to appeal to middle America. No matter what the reasoning, it was a horrible call.

Best Director

John Ford beats Orson Welles: Orson Welles’ direction and innovations on “Citizen Kane” opened up so many storytelling and technical avenues for Hollywood productions than are possible to fathom nowadays. John Ford’s “How Green Was My Valley” was a more traditional and “safe” effort, and Oscar is often known for taking the safe route.
 
Bob Fosse for “Cabaret” beats Francis Ford Coppola for “The Godfather”: One of the most baffling decisions in Oscar history came when Bob Fosse’s competent musical theater direction bested Francis Ford Coppola’s masterful tale of mafiosos juggling their business and personal lives. Coppola was awarded the Best Director prize for “The Godfather Part II,” but most definitely should have won for the first installment as well.
 
Kevin Costner for “Dances with Wolves” beats Martin Scorsese for “Goodfellas”:
Martin Scorsese didn’t win his first directing Oscar until 2006’s “The Departed,” but he should’ve taken it home for “Goodfellas,” his most technically superb movie. Instead, Kevin Costner walked away with the honor for “Dances with Wolves,” a film more notable for its cinematography than its direction. Scorsese crafted a claustrophobic tale of the criminal underworld, but Costner gave the academy what they so often love: an old-fashioned epic.

Best Actor

Rex Harrison in “My Fair Lady” beats Peter Sellers in “Dr. Strangelove”: I suppose I am biased against musicals, but it always amazed me that Rex Harrison’s rather phoned-in performance as Henry Higgins in “My Fair Lady” trumped Peter Sellers’ career-best work as Officer Mandrake, President Muffley AND Dr. Strangelove in Stanley Kubrick’s Cold War dark comedy. I suspect older Oscar voters didn’t know what to make of Sellers’ roles, but maybe they just preferred a light musical to searing political commentary.
 
Art Carney in “Harry and Tonto” beats Al Pacino in “The Godfather Part II”: Art Carney gives a touching performance as a man on a cross-country trek with his beloved cat Tonto in “Harry and Tonto.” It was a nice reminder of Carney’s light comic talents, but nothing compared to Al Pacino’s thunderous, iconic performance as Michael Corleone in “The Godfather Part II.” On occasion, but certainly not always or even the majority of the time, more is more.
 
Roberto Benigni in “Life is Beautiful” beats Tom Hanks in “Saving Private Ryan”: That “Life is Beautiful” was nominated for or won anything is a major Oscar screw-up. It’s definitely one of the worst films I’ve ever seen, and Benigni’s performance does nothing but make a mockery of the Holocaust.

Awarding Tom Hanks’ role as Captain John Miller in “Saving Private Ryan” might have seemed like overkill to the academy after his recent wins for “Philadelphia” and “Forrest Gump.” Regardless, they truly missed the mark by even acknowledging the existence of Benigni’s shit-stain of a movie.
 
Sean Penn in “Mystic River” beats Bill Murray in “Lost in Translation”: Sean Penn overacted the hell out of his role as a grieving father in Clint Eastwood’s “Mystic River.”

At the same time, Bill Murray’s status as a great comic actor was revitalized further after a string of priceless supporting roles. There’s a subtlety and grace to Murray’s performance as strung-out actor Bob Harris that’s completely missing in Penn as he screamed “WHERE’S MY DAUUUUUUUUGHTERRRRRRR?!?!” at the top of his lungs and flailed about wildly.
 
Best Actress

Julia Roberts in “Erin Brockovich” beats Ellen Burstyn in “Requiem for a Dream”: Ellen Burstyn absolutely kills it in Darren Aronofsky’s “Requiem for a Dream.” It’s honestly one of the single best performances I have ever witnessed a human being give, and it has the power to induce laughter, sobs and gasps from me every time I watch it (as difficult to watch as it is).

Julia Roberts won the “likeable actress in a sassy and quotable role” award this time, though. See Sandra Bullock in “the Blind Side” for a more recent example of this.
 
Best Supporting Actor

Joel Grey in “Cabaret” beats Al Pacino, Robert Duvall and James Caan in “The Godfather”: Unfortunately, this was a simple case of a trio of brilliant “Godfather” performances canceling each other out, with Joel Grey there to pick up the leavings. If there’s ever been a case for adding a “Best Acting Ensemble” award to the Oscars, this was surely it.
 
Melvyn Douglas in “Being There” beats Robert Duvall in “Apocalypse Now”: Melvyn Douglas is fine in “Being There,” and, at age 78, it was one of his final film roles. Yet Robert Duvall is absolutely transcendent in “Apocalypse Now.” His Colonel Kilgore steals the movie during his entire time onscreen, and the specter of his lust for war lingers for the remainder of the film.
 
Tommy Lee Jones in “The Fugitive” beats Ralph Fiennes in “Schindler’s List”: Tommy Lee Jones is all scenery-chewing bluster in “The Fugitive,” while Ralph Fiennes in Steven Spielberg’s masterpiece is a monstrous incarnation of genocidal evil in human form. You can actually see death in the eyes of Fiennes’ Amon Goeth. It’s a terrifying performance. In this case, though, Hollywood sensibilities beat historical drama.
 
Michael Caine in “The Cider House Rules” beats Tom Cruise in “Magnolia”: Tom Cruise’s bravest, most deeply felt and expertly acted performance was beaten by Michael Caine, who was just being Michael Caine. I’ve often wondered if the problem here was that academy voters just felt it too easy to loathe Cruise’s Frank T.J. Mackey. In any event, this is the one time in Cruise’s career where he truly deserved to be showered with acting honors.
 
Best Supporting Actress

Catherine Zeta-Jones in “Chicago” beats Meryl Streep in “Adaptation”: Oscar has always been very kind to Meryl Streep, more so in terms of nominations (16) than wins (2). This should’ve been a third win for Streep, it being her most memorable role since Sophie in “Sophie’s Choice.” However, one of Miramax’s relentless Oscar campaigns swept Catherine Zeta-Jones’ sexy but one-note work in “Chicago” along in its awards winnings.
 
Jennifer Hudson in “Dreamgirls” beats Rinko Kikuchi in “Babel”: This was a battle between the overstated and the understated. This time overstated won. “American Idol” alum Jennifer Hudson screeched and bawled her way through her role as Effie in the criminally overrated “Dreamgirls,” while Rinko Kikuchi offered up a heart-wrenching performance as a deaf Japanese teen discovering herself in a world that she understands less than it understands her.
 
Best Screenplay (original)

“Pillow Talk” beats “North by Northwest”: It took four screenwriters to come up with the story for “Pillow Talk,” and, while it’s a fun little romantic romp, it’s still a mid-level romantic comedy at best. Meanwhile, Ernest Lehman’s thrilling screenplay for Alfred Hitchcock’s “North by Northwest” is as ambitious as it is daringly sexual for its time. The academy so often prefers lighter fare, and it showed in its voting here.
 
“Coming Home” beats “The Deer Hunter”: This is mostly an example of the academy’s politics coming into play. Both “Coming Home” and “The Deer Hunter” are films about the horrors of the war in Vietnam, but while “The Deer Hunter” is an unflinching look at how war ravages the minds and relationships of those involved, “Coming Home” takes a slightly more patriotic look at things. Both films are anti-war, but only one delves deep enough into its characters to warrant an Oscar.
 
“Gosford Park” beats “The Royal Tenenbaums”: Robert Altman’s “Gosford Park” is essentially a glorified night at the dinner-theater. The massive cast gives it their all, but Julian Fellowes’ screenplay never rises above being a semi-witty take on the British class system.

Wes Anderson and Owen Wilson’s work on “The Royal Tenenbaums” is possibly the best comedic screenplay of the decade, as it mixes mirth and malice with a nimbleness not seen by many of today’s film writers.
 
Best Screenplay (adapted)

“Becket” beats “Dr. Strangelove”: I’m sure we all fondly remember “Becket.” No? Anyway, the obscure film based on a French play about a medieval Catholic Archbishop bested Stanley Kubrick and Terry Southern’s consistently uproarious take on Peter George’s timely Cold War novel. Maybe the subject matter was too sensitive for the academy, or maybe they were just once again showing their fuddy-duddy preference for the old-school.
 
“In the Heat of the Night” beats “The Graduate”: While the former’s screenplays is nothing to scoff at, Calder Willingham and Buck Henry’s brilliant adaptation of Charles Webb’s novel is filled with so many iconic moments and game-changing nuances (for the film as well as the industry) that its defeat here is stunning.
 
“The Pianist” beats “Adaptation”: “The Pianist” is a first-class Holocaust film with an amazing performance by Adrien Brody, but its screenplay pales in comparison to the Wladyslaw Szpilman memoir on which it’s based.

On the other hand, Charlie Kaufman’s “Adaptation,” based ever-so-loosely on Susan Orlean’s book “The Orchid Thief,” is one of the best and densest screenplays ever written. I have to assume this is a simple case of the academy just not “getting it.”