The 10 Worst Oscar Best Picture Winners of All Time

Filed under: Festivals

In the wake of the grandest celebration of film, one must inevitably ponder the value of such an affair: the millions spent on deluxe cuisine, haute-couture and party favors; the endless road blocks manned by legions of the LAPD, their hands quivering in switch-blade readiness inches above their nightsticks; not to mention the monumental production and advertising costs. We fervently hope that the victors will be worthy of this excess (as though such a thing were possible). We at least hope the best film triumphs.

Alas, such is almost never the outcome. Mediocrity, not vision, often seems to possess a sizable advantage, as though the AMPAS voters' picks were perpetually moderated by a fear of originality. Amidst the winners of middling scope sit those who rank somewhere below the others -- the truly terrible film that seems to have used black magic, subliminal messaging or some other nefarious technique to seduce the Academy. Once the spell wears off, the film world stands aghast as the interlopers (aka crappy filmmakers) smugly grasp their tin statuettes. With no further ado, I give you my list of the ten worst Oscar Best Picture picks of all time.

Note: I freely admit that I've seen only a fraction of the 83 Best Picture winners and that my choices gravitate heavily to the last ten years, demonstrating my position in the fluxing dimension of time. Additionally you will note a bias in anti-favor of musicals. It would not surprise me if I haven't even seen the worst.

10) Slumdog Millionaire

Once the freshness of director Danny Boyle's frenetic style has oxidized to a dull patina through the tide of time, viewers will see a film rife with clichés and as gimmicky as a Charles Dickens novel. The film's "internationalism" (a British filmmaker adapting an Indian novel starring Indians speaking English) bolstered its clout in an age when everyone is increasingly sensitive to issues of globalization. In the end, I fear the combination of Boyle's style and a reliance on pop culture references will result in this film aging poorly.

9) My Fair Lady

From Audrey Hepburn's terrible cockney accent to the excruciating and unnecessary 170 minute runtime there's a lot to dislike about this chauvinistic tale of a man making over a woman to fit his ideal. The shining moments of screwball comedy are far too lean for a film of such massive girth -- most of the film is an exercise of the dullest sort. I suspect that the popularity of the Broadway musical had a lot to do with the Best Picture victory. (Fun Fact: Julie Andrews originally played the part of Eliza Doolittle on Broadway, but the producers believed she was not famous enough to carry the film. Instead, they cast Hepburn, who could not carry a tune, resulting in all her singing parts being dubbed.)

8) Shakespeare in Love

In all honestly, this film is more mediocre than terrible, though I doubt anyone feels a need to watch it again. However, it lands in the bottom ten because its competition for Best Picture was Terrence Malick's The Thin Red Line. Since this perfectly demonstrates AMPAS's typical siding with lackluster filmmaking as opposed to vision and ideas, I felt this was worthy of inclusion.

7) The Broadway Melody

Remembered for its tiresome showbiz clichés and awkward performances, the second Best Picture winner in Academy history won in a year where apparently the competition was none too fierce -- it ranked top dog amongst a pack of mangy curs. I'll admit that I've never seen this film and likely never will but its legacy as the first filmed musical (a genre which in my opinion should never have left the stage) seals its place in the bottom ten.

6) Terms of Endearment

Schmaltzy, sentimental tripe. This film definitely deserves all the disdain the term "chick flick" implies. Audiences tend to believe that just because they leave a theater with swollen red eyes and a snotty hanky, they experienced something worthwhile as opposed to simply emotionally manipulative. Pretty much the film's only redeeming quality is that it's not Beaches.

5) Chicago

Outside of the sequined negligees and innovative lighting design, there truly is little that gives this film dazzle or color. When I reread the plot synopsis for the purpose of writing this article, I realized I had forgotten even the most salient plot points. What I do remember with stunning clarity is my first impression of feeling wholly underwhelmed. The experience of watching Chicago is like opening a beautifully wrapped present to discover an empty box -- superficially enticing but hollow on the inside.

4) The Greatest Show on Earth

Master of the grandiose, Cecil B. De Mille's circus melodrama is widely regarded as one of the worst Best Picture winners of all time. Ironically, it also is one of the biggest grossing films of all times (when adjusted for inflation). Like so many box office giants, Greatest Show is all spectacle with no substance.

3) West Side Story

Arguably, the hit Broadway musical was never really adapted into a film as the production design appears to have barely been altered from the stage. One is left with the impression that he or she might have had a lot more fun attending a live performance. Lazy play adaptation stands as one of my primary pet peeves, but West Side Story further fails with its terrible musical compositions -- literally some of the most whiny tunes ever churned out ("I feel Pretty", uuhhhhgg!) which is saying a lot.

2) Crash

Probably one of my most loathed Best Picture winners of all time. This film is not only emotionally manipulative but also brimming with its own self importance. I will admit that on first view, the wannabe profound insights into race relations in Los Angeles, human nature or whatever it was trying to say almost work. The viewer walks away from the theater feeling content in having seen a quality piece of filmmaking; then, possibly several days in the future, feels a sudden jolt of shame at having fallen for such a trite and emotionally shallow piece of work -- kind of like coming out of a bender and remembering all the embarrassing things you said and did while inebriated.

1) Gone with the Wind

This pick is destined to raise an eyebrow or two. The 1938 classic paradoxically stands as both one of the greatest and worst films of all time. One might ask what's not to love: an epic story of passion and a gripping depiction of the war that nearly tore the United States asunder all brought to vivid life in Technicolor film. But deep at its core, Gone with the Wind is a loving farewell to the Old South -- a society that enslaved other human beings in order to sustain a life of gentrified stagnation and shameless excess. The black characters are portrayed as stupid and/or idolatrous of their white masters. While some might be tempted to excuse the film's racism as retrograde folly, I believe it is too deeply part of the ultimate message. In the end, it is impossible to separate a work of art from its context.

Tags: Oscars, Gone with the Wind, My Fair Lady, Shakespeare in Loce, The Broadway Melody, Terms of Endearment, Chicago, The Greatest Show on Earth, West Side Story, Crash

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Original Comments Posted (3)

crimson says...

I liked Chicago!

Mar 6, 2011 5:34pm

Mike Walkey says...

Total agreement on Crash!

Personally, I've always thought Gladiator (2000) was overrated.

Mar 9, 2011 9:00am

crimson says...

I liked Gladiator!

Mar 12, 2011 8:46pm

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