Any list of the 'worst' anything is naturally subjective, but when looking back at the history of Best Picture winners, some decisions by the Academy seem especially egregious when compared to films that could (should?) have won instead. The following were deemed classics at that time but haven't aged especially well, like... Rain Man A solid opening and closing act bookend what is otherwise a frustratingly uninvolving and meandering mid-section in which Tom Cruise and Dustin Hoffman do their best as an arrogant salesman and his estranged autistic brother. I won't go as far as critic Pauline Kael who called it 'a piece of wet kitsch,' but it's pretty soggy. Could've/Should've: Women on the Verge..., Who Framed Roger Rabbit, Bull Durham, The Vanishing, Unbearable Lightness of Being, Die Hard, Dangerous Liaisons.
By Craig Phillips
To many, a powerful, resonating look at issues of race and loss set in tumultuous times; to some, an often obvious and heavy-handed thesis more than a flowing, believable film. Though its many good actors bring their all--like Thandie Newton and Don Cheadle--the film succeeds in making one angry, but less so about the issues at hand than about Paul Haggis' overreaching script, with annoyingly contrived dialogue. It's well-meaning--I give Haggis props for trying but the film ultimately feels, well, trying, and several stereotyped ethnic characters don't help the cause. And yet Hollywood patted itself on the back by handing it the Oscar. Could've/Should've: Brokeback Mountain; Good Night and Good Luck; Cache; The Squid and the Whale; The Constant Gardener; Batman Begins; Munich.
Out of Africa
Based on Isak Dinesen's well-regarded, semi-autobiography and starring Redford and Streep, directed by the always reliable Sydney Pollack, this period romantic drama had loads of Oscar cred. The film's strengths are Streep and its beautiful photography, but the love story at the center is mushy pap and the whole gauzy thing's not nearly dramatic enough to warrant the 160-minute running time. Could've/Should've: Witness, Ran, A Room With a View, Prizzi's Honor, Kiss of the Spider Woman, My Beautiful Launderette...and so many other great films in 1985 that were better than this one.
Around the World in 80 Days
I didn't expect to put this Jules Verne adaptation here, but boy, after revisiting, it really felt like an 80-day long slog. There are charming moments and exotic locales, but it's a long turgid trip in between them; the pacing is a slowly deflating balloon. The Academy got it all wrong in 1956: The King and I and Ten Commandments were two other bloated Best Pic nominees, while overlooking... Could've/Should've: The Seven Samurai, The Searchers, Written on the Wind, The Killing, Invasion of Body Snatchers, The Court Jester.
A bit misinterpreted when adopted by conservatives in the '90s as a rebuttal to 'hippie/liberal ways,' but the satirical edge from Winston Groom's novel (and, as the author himself said, the 'rough edges of the character') was somewhat blunted in Zemeckis' film, which never really emotionally engages the way it should. It goes from point A to B to Z with series of impressive effects, while trivializing history and inadvertently celebrating stupidity. As for 'Everyman Who Ends in Famous Places/with Famous People' stories, give me Zelig anytime. Could've/Should've: Pulp Fiction, Quiz Show, Shawshank Redemption, Red, White, Heavenly Creatures, Hoop Dreams, The Lion King.
The Greatest Show on Earth
In this cinematic equivalent of a motel clown painting, Jimmy Stewart plays a perpetually sad clown while Charlton Heston hams it up as a circus manager in an episodic soap opera set under the big top. Give it props for some interesting asides about circus life, but Cecil B. DeMille (yes, him) lays it on thick enough that you start rooting for a Siegfried & Roy-type tiger mishap. For odd salutes to the circus world, I'd rather watch Fellini's The Clowns, and, frankly, I'd rather not watch that either. Could've/Should've: Singin' in the Rain (not even nominated!), High Noon, The Quiet Man, Forbidden Games, Ikiru, Limelight, Umberto D.
The Great Ziegfeld
A 3-hour biopic on theatrical impresario Florenz Ziegfeld (a willing and able William Powell) seemed dated 10-15 years after it won the Oscar, and even more so today. MGM hired hand Robert Z. Leonard's film is overlong, the drama's dull and even the musical numbers are surprisingly torpid. All told, it's not great, but there is indeed a lot of Ziegfeld. Could've/Should've: Modern Times, Camille, Fury, My Man Godfrey, Swing Time, Mr. Deeds, Libeled Lady, San Francisco.
Cornball, melodramatic epic based on Edna Ferber's novel, this 'sweeping' (in this case, that means full of admittedly lovely Western landscapes and a bloated running time), this frontier tale wasn't even a box office hit in its own era; and offers up quite dated (i.e., racist) depictions of Native Americans to boot. Even the normally lovely Irene Dunne is miscast and over the top here. Could've/Should've: City Lights, Public Enemy, The Front Page, Frankenstein, M. Note: Cavalcade, from 1933, is the only Best picture winner to not have an individual DVD release. While it's considered to have not aged well by some who've seen it recently, I haven't seen it myself...
Not terrible, but this creaky Dickens-inspired musical is of a type of musical that has been satirized too much (see: Mr. Show or Monty Python's Meaning of Life) since then to take seriously. Consider yourself...warned: Some of its 'classic' songs also go on for torturous length. This is not Carol Reed's finest hour (or two and half). To be fair, it wasn't the strongest year for Best Pic nominees (Funny Girl, The Lion in Winter (which would've been my pick), Rachel Rachel and Romeo and Juliet were the others), but in a year that also gave us 2001: A Space Odyssey, Faces, If..., Charly, Planet of the Apes, Rosemary's Baby and The Producers--even knowing the Academy's aversion to genre, this is in hindsight collectively one of the stodgiest Oscar failures. Could've/Should've: All of the above.
Dishonorable Mention: Chicago; Titanic (easily could've been on this list but I admit to digging the final act); How Green Was My Valley (I'm not a hater of John Ford's Welsh-family saga at all, but given it was chosen over Citizen Kane, The Maltese Falcon, Suspicion and Here Comes Mr. Jordan among others... hard not to scold the pick anyway); Mrs. Miniver; Slumdog Millionaire; Rocky (only because it's worse than the 4 other excellent films--Taxi Driver, Network, Bound for Glory and All the President's Men--it beat out, not because it's all that bad).