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As we creep closer to the 2009 Academy Awards, prognosticators look back as much as forward to try and determine who the favorites will be. By looking back, I mean to suggest that past Academy choices perhaps unfairly paint them in a certain light, and support the group's predictability and oft-whispered bias. For instance, feel good films generally trump depressors. Oscar loves a comeback story almost as much as they love to reward seasoned veterans with lead acting awards and fresh faces in the supporting roles (particularly supporting actress). And despite a requisite surprise or two every year, they mostly play it safe. Usually painfully boringly safe. That, and the fact they get it wrong more often than they get it right. So I present a glance at the ten most egregiously shortsighted Oscars ever given.

I'm focusing solely on the big one: Best Picture. If I included anything and everything, I could go on for hours (and be forced to do more research than I care to devote to something as essentially superficial as an award given to Hollywood from Hollywood). But it's tough to ignore the Academy Awards, as ego-inflating as they are. With only a few exceptions (Marlon Brando, George C. Scott), everyone in the biz wants one and treasures receiving it. And the ceremony is one of the highest rated television broadcasts each year—some treat it with the frothing enthusiasm usually reserved for something like the Super Bowl. But enough pondering the worth of an Oscar; let's see where the Academy screwed up royal.

To keep things fair (and concentrated), I only consider the films that were nominated. Truthfully, they almost never pick the actual best movie of the year (all those Dark Knight diehards out there would agree). Off the top of my head, they picked well with the first two Godfathers, Casablanca, Schindler's List, On the Waterfront...and I'm running out. Even Waterfront skates by with the technicality that from the same year, the greatest action film of all time, The Seven Samurai, only became Oscar eligible two years later (no idea about the reason). But if I considered every film released in any given year, it would be too tough to narrow it down (and the research...oh, the research...). And to keep it even more fair, I've also made it a rule that a) I've seen the movie that undeservedly won, and b) I've seen at least four of the movies nominated altogether. Therefore, I eliminate myself of several notoriously scorned Best Pic winners like Around the World in Eighty Days, Chicago, The Greatest Show on Earth, Cimmaron and The English Patient. How can I say they didn't deserve it if I've never seen them? Also, since I need to have seen at least four of the nominees, there'll be no rage over the snub of Raging Bull—haven't seen fellow nominees Tess or Coal Miner's Daughter. So, as filtered through my restrictions, here's the ten biggest mistakes (in reverse order):

10. Driving Miss Daisy (1989)

In 1989, there were three well-respected but very different films that dealt with racial tension; Driving Miss Daisy is easily the most genteel...and the weakest. The other two (Do the Right Thing and Glory) deserved nominations. Daisy did not. As will soon become abundantly clear with many of my other selections, this is like most other erroneous choices: the played-out example of a good-looking and well-acted film (even Dan Aykroyd nabbed a supporting actor nod), but with a screenplay that's flimsy and usually surface deep in its examinations. It's an entertaining movie, to be sure, but it would have been more effective if both characters had to traverse a personal distance to arrive at their friendship—Hoke was too eager to please and we rarely saw him become truly rankled by Miss Daisy's crotchety stubbornness. And due to its episodic nature and relatively brief running time, it's not always easy to connect the dots between the years to see how the relationship blossomed; instead, the hearts opened in fits and starts through “too obvious” dramatic situations. I prefer the version from The Critic where Hoke changes his name to Malcolm H and informs Miss Daisy that when the revolution happens, she will not be spared. Oh, so satisfying.

Other Nominees: Born on the Fourth of July, Dead Poet's Society, Field of Dreams, My Left Foot

It's a relatively uneven pool of choices. Field of Dreams defies the odds and shifts back and forth from whimsical to heartfelt, but while it works in the moment, retrospect unravels a few minor problems. I've never been a big fan of Dead Poet's Society; I found the characterizations to be too pat—everyone was either ennobled or venomously authoritarian. Born on the Fourth of July proved that Tom Cruise could hold his own with a rich dramatic part but it takes a few too many detours along the way that diminished the impact of Kovic's character arc. My Left Foot contained both the year's most intriguing character and best performance (ably supported by a fine cast). For those three people on the planet not impressed by Daniel Day Lewis' work in films like Gangs of New York and There Will Be Blood, check this one out. If you're still a naysayer to his talent, I have nothing further to say to you.

Shoulda Won: My Left Foot

Haven't Seen: None

9. Gone with the Wind (1939)

I fully admit that there was no other choice that Oscar night. Gone with the Wind was a massive, old-style, sweeping epic and despite its hefty price tag (for the time), it became a box office sensation. Adjusted for inflation, most estimates indicate that its one of the highest grossing movies ever, if not the highest. Frankly, if it hadn't have won, I'd be stunned. But size and popularity doesn't necessarily equate to quality (see #1), and despite mostly good performances and a terrific transfer that keeps that beautiful three-strip Technicolor vividly alive, this is pretty much a sudsy dud all around. The main character, Scarlett, despite being well-played, is so utterly unlikable that summoning sympathy for her plight is tougher to do than to watch this nearly four-hour behemoth in one sitting. I, like Clark Gable at the end, just didn't give a damn. That's not to say that the focal point in a film needs to be affable (look at the excellent There Will Be Blood), but I sense that the source material and filmmakers were aiming for us to “fall in love” with the flawed character. Didn't happen. I could also mention the racist overtones that bleed through quite frequently: “birthin' babies” and Mammie's happy indoor slave routine, among others; not to mention an infamous scene that ended up on the cutting room floor depicting a Klan-like group in the same heroic light as Birth of a Nation. But that's not all that important in judging this movie's pure worth...seeing as how filmmaking owes a tremendous debt to the far more morally-repulsive Nation's breakthroughs.

Other Nominees: Dark Victory, Goodbye Mr. Chips, Love Affair, Mr. Smith Goes to Washington, Ninotchka, Of Mice and Men, Stagecoach, The Wizard of Oz, Wuthering Heights

Lucky for me, my “four nominee rule” applies to the handful of years when there were ten films in the running; I haven't seen half of the choices. So if not Wind, then what? Most dissenters, I suspect, would thrust a finger at Wizard of Oz. But like Wind, I've never been much of a fan of Oz (I know, stone me). The innovation and production design is worthy of respect, yes, but it's played too broadly for my taste, even for a family film—it's camp without the cult-worthy kitsch. Dark Victory was even more of a silly soap opera than Wind, and is awfully outdated. Mr. Smith might seem a good choice since it's a deserved classic, and one of the few Frank Capra efforts I've seen that didn't have too much saccharine for me to stomach (again, stone me). But I'm tipping my cap for John Wayne's best Western (narrowly beating The Man Who Shot Liberty Valance and Red River). It's a star-making turn for the Duke and perhaps the most impressive adventure movie of its era.

Shoulda Won: Stagecoach

Haven't Seen: Goodbye Mr. Chips, Love Affair, Ninotchka, Of Mice and Men, Wuthering Heights

8. Out of Africa (1985)

Comparably, Gone with the Wind is a thrill ride to this snoozefest, which is saying something since I'm usually annoyed by most films' inability to revel in the quiet moments. Meryl Streep is always good, but the usually reliable Robert Redford fades into the scenery, and the two of them elicit half a spark at best—the only rooting interest in their romance comes from the knowledge that at least he's a better guy than her philandering husband. The accents were bothersome, too—Streep's Danish character needed something to inflect her speaking, but the stilted manner in which she spoke made the more dramatic speeches sound long-winded and unemotional. Redford played a Brit, but he rarely sounded anything but American—reportedly, it was the director's choice, not Redford's.

Its victory reveals the Academy's bias for big dramas, and also proves just how few good prestige pictures there were during the 80s (but it had a surfeit of great entertainments). Like Wind, it's a great-looking picture with a couple of good performances, but lacks the weight for the drama not to curdle into melodrama—its occasional snail's pace doesn't help, either. A lack of phenomenal competition alone keeps this one from appearing higher on the list (er, lower?).

Other nominees: The Color Purple, Kiss of the Spider Woman, Prizzi's Honor, Witness

It's a mildly underwhelming field (excepting perhaps the one I haven't seen). Despite all of his good intentions, The Color Purple was about as inert and uninvolving to me as Africa, a result I never expect from Steven Spielberg—I can't explain it nor can I deny it. Witness is good, but a little too predictable and contrived at a few junctures; still a flawed winner. Prizzi's Honor was an atypical nominee—a quirky black comedy. With sharp writing, fine performances all around and a few neat twists, I imagine that the value of its actors and director was too much for the Academy to overlook for a nod.

Shoulda Won: Prizzi's Honor

Haven't Seen: Kiss of the Spider Woman

7. How Green Was My Valley (1941)

How Green Was My Valley is actually a pretty good movie. It plays well into the perceived bias of the Academy, being a richly textured study of setting and circumstance, family and tragedy. And considering that the movie is almost seventy years old, it's a pretty sophisticated production, with only a handful of overly histrionic moments to make the audience grimace. The movie also customarily sacrifices realism for sentimentality, which some will appreciate more than others. But it's still a handsomely mounted film with good performances (considering he's a child actor, Roddy McDowall is actually quite good). This selection isn't about the Academy choosing a wholly unworthy picture; this is about how they neglected far superior choices.

Other nominees: Blossoms in the Dust, Citizen Kane, Here Comes Mr. Jordan, Hold Back the Dawn, The Little Foxes, The Maltese Falcon, Sergeant York, Suspicion

Of the five total I've seen, How Green Was My Valley is the limpest by a hair. Gary Cooper may never have been better in his career than he was in Sergeant York, an oft-neglected war movie classic. Suspicion is one of many great Hitchcock efforts with great performances all around (too bad the ending was butchered by the Production Code). The Maltese Falcon needs no further explanation than this: it's an undeniable noir masterpiece that gets better every time you see it. And, oh yeah, some movie called Citizen Kane was in there, too. You might have heard of it.

Shoulda Won: Citizen Kane

Haven't Seen: Blossoms in the Dust, Here Comes Mr. Jordan, Hold Back the Dawn, The Little Foxes

6. Rocky (1976)

Same as How Green Was My Valley, Rocky is a truly satisfying motion picture and the character is a huge Hollywood icon. It was a sleeper hit, a crowd-pleaser and an enormous rarity—the Academy went for a genre picture. Despite the fact that Sylvester Stallone is usually recognized as a sub-par actor, his performance and screenplay for Rocky were both dependably solid. And when you ignore the slew of sequels that tarnish its legacy (some were okay, most were beating a dead horse), the movie seems even more impressive. It was a long shot for both Sly and the character he played, so seeing the underdog triumph probably wasn't too disappointing; only the aftertaste is bitter. Even people disinterested in the “sweet science” (like, um, me) can be thrilled by the training and boxing sequences. But also like Valley, this isn't about how the winner wasn't any good; it's about what movies it beat.

Other Nominees: All the President's Men, Bound for Glory, Network, Taxi Driver

Considering that everyone who watches the movie knows how it's going to turn out, All the President's Men is astonishingly suspenseful, and watching the pieces of the mystery fall into place is a thrill even on a third and fourth viewing. Network remains one of the smartest and most scathing satires ever committed to celluloid; one that keeps its claws sharp from the first to last frame. And Taxi Driver, no matter how painful it can be to watch (for me, it's not the climactic violence but Bickle's uncomfortably awkward social transgressions that increase his abject isolation), you just can't look away. It certainly wouldn't be the only time that Scorsese was robbed. Hell, he didn't even get a directing nod for this one.

Shoulda Won: Taxi Driver

Haven't Seen: Bound for Glory

Countdown continues on Page 2.