Every year, we film fans go through the award gauntlet of agony and ecstasy. We champion our favorites for nominations, rant for weeks if they’re snubbed, or cautiously root for them to be revealed as the prize winner. If they’re shut out, we declare it’s the worst offense to cinema in the history of moviemaking. That claim will hold until the next year, when the game will begin all over again with a new round of favorites.
But we fail to realize that snubs and shutouts have been endemic since the very first Academy Awards ceremony, and that some of the greatest films of all time lack a glittering trophy. In fact, one might be tempted to argue that losing an Oscar is more prestigious than winning one. To remind us of that fact, here’s 12 films the Oscar misguidedly rewarded over the ones you really love, remember, and cherish.
The sad thing? There’s a lot more than 12. You’re free to add to the list (and disagree with the ones I’ve listed) below in the comments.
Here’s a list of films the Academy was right on.
(Pay no attention to the numbers, as they’re not intended as a rank. The years listed after the film reflect the year the Oscar was awarded, not the year the film was released. I’ve done this to be in line with IMDB’s listings.)
1. Crash (2006)
Let’s warm up slowly, and start with a fresh wound. Brokeback Mountain was the critical darling, and predicted to sweep the Oscars. It was supposed to be the sign of a new and tolerant world. It turns out, the Academy was still squeamish about two men who can’t quit each other. But in a fit of PC pique, they gave it to Crash because, well, it was kind of like giving it to Brokeback Mountain, wasn’t it? No. Not really.
2. Titanic (1997)
This wound of a win has been reopened by the heady Avatar love. Now, I’m not a Titanic hater. I was young and impressionable in 1996 and I saw it several times in the theater. I wept each time. I cheered it on at the Oscars. Then I finally grew up, went to college, and watched L.A. Confidential. I immediately fell in love with it, and the film is now one of my all time favorites so that I share in the great anger of 1997. Yes, Titanic was a breathtaking spectacle, and it deserved all awards that honored that – costumes, set design, sound, etc. But L.A. Confidential is brilliant, and as old-school as they come. The Academy should have recognized which movie was really the throwback to classier, cooler filmmaking.
3. The Greatest Show On Earth (1953)
It’s the most legendary of ill-given Oscars. Do you remember this movie? That’s ok, no one does, though it was the highest grosser of 1952. But I imagine you do remember High Noon and The Quiet Man. I bet you can even sing and dance to the legendary Singin’ in the Rain which wasn’t even nominated. Nor was The Bad and the Beautiful, which has been preserved by the Library of Congress, an honor not yet given to The Greatest Show On Earth.
4. Driving Miss Daisy (1990)
Driving Miss Daisy is a charming film. But should it have beat Born on the Fourth of July, Dead Poets Society, Field of Dreams, or My Left Foot? Should it or Field of Dreams (and yes, I do love that film) have beat out Glory or Henry V for Best Picture slots? I don’t know. But I do know that 1989 wasn’t a weak enough year for Driving Miss Daisy to have won Best Picture as has often been claimed.
5. Around the World In 80 Days (1957)
A criminal year. 80 Days beat the far superior Giant, which is bad enough. But the worst of it was that The Searchers wasn’t even nominated for Best Picture alongside The King and I, Friendly Persuasion, and The Ten Commandments. John Ford and John Wayne have had their revenge, but it remains a historical fact that the Academy often doesn’t know what the heck they’re doing.
6. Gigi (1959)
There must have been something terrible in the water in the 1950s. Or perhaps confusion reigned due to radioactive fallout from Los Alamos, or a lingering post-war malaise. Whatever the cause, it led Gigi winning over the far superior Cat on a Hot Tin Roof. But even worse? Neither Vertigo or A Touch of Evil were nominated. But Auntie Mame was. It may be a good film, but it is neither as legendary nor essential as Vertigo is.
7. Chariots of Fire (1982)
It never fails to surprise me that Raiders of the Lost Ark was actually nominated for Best Picture in 1982. It’s like I’m always hearing that for the first time. It should have won. But this is one of those times when the Academy felt simply nominating it was enough, but that the statue really had to go to something classy and European. (Even the combination of Katharine Hepburn and Henry Fonda in On Golden Pond wasn’t enough to dissuade them of the notion.) To this day, the majority of moviegoers only recognize Chariots of Fire as “that movie where the guys jog to Vangelis.”
8. Oliver! (1969)
Oliver! is a classic musical. A lot of people adore it. But it’s no A Lion in Winter. Critics who favor “Who Will Buy?” over “I could peel you like a pear, and God himself would call it justice!” are critics I cannot like or respect. You probably agree with me when you realize 2001: A Space Odyssey wasn’t even nominated, but Funny Girl was.
9. Forrest Gump (1995)
I confess, I have always hated Forrest Gump. I hated it the first time I saw it in the theater, and I feel like I must have seen it a million times because my family loved it so much. But it’s cloying and embarrassing, and a thousand Bubba Gump shrimp restaurants can’t change the fact that Pulp Fiction or The Shawshank Redemption should have won. You can try and decide which one deserved it more, though.
10. Chicago (2002)
Chicago was allegedly the hot thing that year, but the craze was so obviously a Miramax manufacture that it was sad to see the Academy fall for it. Again. There were a lot of films more deserving of Best Picture – Adaptation, Far From Heaven, The Hours, Catch Me If You Can, Road To Perdition, and Lord of the Rings: The Two Towers. You can even make an argument for the flawed Gangs of New York, though I won’t. But I will ask who among you even had Chicago on their Best of Decade lists.
11. How Green Was My Valley (1942)
I love John Ford, and this film is a beloved classic for a lot of good reasons. It’s not a bad film, like many of the winners on this list. But it shouldn’t have won over Citizen Kane or The Maltese Falcon. This was a 10 nominee year, by the way, which can just show how awkward that can become.
12. Shakespeare in Love (1998)
I’ll bow to the popular consensus on this, though I’m not ashamed of how much I adore Shakespeare in Love. It’s one of those films that’s just tailor made for an English nerd like me. I also feel that Saving Private Ryan was overrated beyond the harrowing D-Day sequence. But there’s no doubt that this was the fluffiest pick out of a year that included The Thin Red Line, Saving Private Ryan, Gods and Monsters, and American History X.
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Words cannot express how happy I am to see Crash on this list. What a horrid film.
I DISAGREE with CHICAGO. It was my best film of the decade. It deserved best picture!!!
hell yes!
Chicago deserved the Oscar!
I do agree with Chicago and Titanic. Chicago was a terrible film, I have never watched the whole thing and have no intention of it. Titanic was ok, but LA Confidential and Good Will Hunting were far better. Never saw Brokeback and will never see it, so Crash was good enough for me, but I did like Munich and Capote more. I also thought Aviator and Finding Neverland were better than Million Dollar Baby. I also thought Frost/Nixon was better than Slumdog and I did not think Benjamin Button or The Reader deserved to be nominated,.
As for this year, I find the fact that The Blind Side was nominated laughable, over movies like Moon and Star Trek. I also don't see the fuss over Sandra Bullocks performance. Was this such a weak year for acting that Sandra Bullocks performance is the best? I thought Zoe Saldanas performance in Avatar was better than Bullocks.
Considering how much I disagreed with your list of what Oscar "got right", I am surprised I agree with a lot of these. And of course I believe some of your "got rights" belong here! (No Country For Old Men–in what was a crappy year in general–among others.) I certainly don't think Driving Miss Daisy deserved it any less than a couple of those.
And in a pipe dream I was hoping I'd see Rain Man on here, because while it's entertaining I don't think it's nearly as worthy as Dangerous Liaisons, and neither were the other three that year. But then you don't seem to prefer the costume pieces–thankfully there are those who do!
(And yes, Braveheart would be ON TOP of this list for me–well, maybe after The Greatest Show on Earth.
)
Actually, I love costume pieces. If we hadn't been keeping it to 12, Dangerous Liaisons would have been on the list over Rain Man. Oscar has gotten so many wrong over the years that it was actually easier to make this list than the one that Oscars got right.
You have a crappy taste in movies. The Academy may be terrible when it comes to rewarding great films but the one getting things wrong here is you.
The funny thing is that you really prove an old agage true: you really don’t understand a lot of movies you critisize – both the winners and nominees.
Well said Kathy. I agree, Brokeback Mountain was an amazing achievement in film, and for someone to even say, that they have no intention on watching it, shows that he is not interested in film as art. Any other movie that year would have been fine, but to award the prize to a sub par film as Crash? Give me a break!
Shakespeare in Love should never have won Best Picture, it was a silly farce. And Chicago? PuhLeeze!
I must say I do agree with those films (except two) you mentioned above about NOT being correct choices for Best Picture awards. But I do say that I liked How Green Was My Valley a lot and did like The Greatest Show on Earth too (most likely because of Charlton Heston). But I've got to add that there are many more that rotten "academy" gave thatcertainly and definitely weren't worthy.
p.s. As far as that "person" saying above he never would see BBM – you are the very epitome of the AMPAS' so-called voters (or in this case non-voters and whispering campaigns). Brokeback Mountain is one of the finest classics ever made.. And to see it lose Best Picture to something so bad & unworthy as "TRASH" is a crime. Well, homophobia is alive & well with you and AMPAS. TRASH is nothing but a joke and everyone knows it. So sad there is still such antagonism towards a beautifully acted, touching & tragic love story as BBM. You deserve 'TRASH".
If you praise Unforgiven (on your other list) as being “still watched and talked about”, you’d have to concede that Titanic fits the bill as well. Now I just watched L.A. Confidential when TCM recently aired it, and found it fit nicely in 1997 but has since fallen off my radar. And I distinctly remember wondering what the big deal was about Kim Basinger’s performance, and still feel the Oscar that year should have gone to Joan Cusack, but I digress.
Gigi I saw last summer and was just as delighted as I was when I saw it on TV as a kid–even more because I understood the story this time, and didn’t have to sit through commercials. So IMO you can switch that film from this list to your other. Switch it with Braveheart.
Speaking of TCM,. last year they held a contest for one viewer to pick and discuss four films and introduce them on air with Robert Osbourne. The winner actually picked The Greatest Show On Earth. I wonder what some of the losers picked! (He redeemed himself later when they showed the fantastic silent film, The Crowd.)
I wont comment on the whole list here but Titanic should not be dragged in this list.Titanic is a master piece & no fingers should be raised against it for getting Oscars.
If you praise Unforgiven for being "still watched and talked about", wouldn't you concede that Titanic fits that bill also? I just watched TCM's recent airing of L.A. Confidential, and truly deserving BP* material would have had me just as rapt as when I first viewed it–and, not so much. (*OT: My local BP mini-mart carried a rack of previously viewed DVDs–and sure enough, LAC is not among them, so it's really not BP material!) I also think Kim Basinger's Oscar that year should have gone to Joan Cusack, but that's another debate for another day. Titanic deserved it, IMO (and I am a grown up, was grown up when it came out).
Gigi I saw last summer–and for one thing it was more faithful to Collette's story than Cat On A Hot Tin Roof was too Tennessee WIlliams' original work. I love all the films you mention, (including Auntie Mame–don't you mess with that one on me!), so it was a very competetive year. But I would still tip my hat to Gigi. I'd switch it to your other list. Switch it with Braveheart.
You are spot on about Crash and TGSOE. I think in years to come, people will say about this current decade what you say about the fifties, but since you like two of those movies you may feel otherwise.. We'll see who's right at the rest home for old movie lovers.
InXandu, i just want to say that you should realize that the absence of LA Confidential on a previously viewed rack means that nobody is reselling the video and as such they are keeping their dvds to re-watch them which negates your argument that it doesn't have replay value.
You do realize the DVD-rack comment was just a joke she or he was making in reference to "BP" right?
Braveheart – 1996
SE7EN!!! It's one of the greatest of all time and not even a nomination? It should have won! The Usual Suspects is definitely a great one too, much better than Braveheart.
Dances with Wolves – 1991 (How come no one's mention this?!)
GoodFellas is so much better, a masterpiece. And in my opinion the slightly underrated The Godfather: Part III is definitely better as well.
Ordinary People – 1981
I think Ordinary People is a good film, but Raging Bull is quite better. It is one of Scorsese's best and that doesn't say little!
Kramer vs. Kramer – 1980
Again, Kramer vs. Kramer is a great film, but Apocalypse Now is one of the best.
Crash – 2006
SIN CITY!
Shakespeare in Love – 1999
The Big Lebowski!
I'm thinking you may have overdosed on testosterone.
I think People need to get over How Green was my Valley beating Citizen Kane, Especially when Orson Welles complimented it and said if he lost it would be that…
How green was my valley deserve to win
what? are you kidding me?? forrest gump didn´t deserve the oscar? pulp fiction and shawshank are outstanding to, but forrest gump is one of the best pieces hollywood ever made!
just because you hated it doesn´t mean everybody else has to;)
The people who are amazed that Shakespeare in Love won don't know some basic facts about people in the entertainment industry. Experience teaches me that, as a group, they are the most insecure people in the world, but this is most particularly true of actors. They also like to think they are "artists" even when they're making schlock like Crash or Titanic you name it. So how could they avoid giving the top prize to a picture that made their profession look as good as Shakespeare In Love did? They looked in that mirror and say nobler, braver, kinder and more generous versions of themselves. They want us to like them, they really, really do.
1967 – In the Heat of the Night
Bonnie and Clyde & the Graduate
1980 – Ordinary People
Raging Bull
1990 – Dances With Wolves
Goodfellas
1996 – The English Patient
Fargo
2000 – Gladiator
Traffic, Almost Famous (not nominated), Memento (not nominated)
2003 – The Lord of the Rings
Mystic River & Lost in Translation
2008 – Slumdog Millionaire
Wall-E (not nominated)
Fried Green Tomatos, one of my favorite movies EVER should have at least been nominated. The cast was AMAZING and the script beautiful. What about 1940's The Philly Story? Should have had an Oscar, it gave Jimmy Stewart his only statue, Kate Hepburn was beat out by Ginger Rogers. Great movie.
I would say "Bonnie and Clyde" and "Fargo" are the two most-shafted films among those you do not mention.
You should have stuck to your guns on Shakespeare in Love. It was a better movie than the other nominees – or at least, not appreciably weaker than they were. Saving Private Ryan was 25 minutes of breathtaking followed by 2+ hours of routine.
Add instead English Patient over the indispensable Fargo.
And I am so glad you specifically focused on Lion in Winter losing to Oliver! instead of just pointing to 2001. And don't get me started on what Oscar has done to poor Peter O'Toole.
It's criminal! He has come up against some incredible performances, but Peter O'Toole deserved to win for Becket or Lion in Winter. I would also argue he deserved to win it for Goodbye Mr. Chips over John Wayne — who deserved a lifetime achievement award over anything for one specific performance, even if it was Rooster Cogburn.
I'd love to just do a list of performances that were robbed. O'Toole would be at the top for certain.
The Lion in Winter was AMAZING. The cast was out of this world and the acting was…WOW
Shawshank Redemption = Supreme Shaft.
I agree. But I seriously doubt they didn't give the Oscar to Brokeback Mountain just because they were "homophobic". Now, I don't think Crash nessisarily should have won, but I don't think Brokeback Mountain should have, either. No offense, but I think the reason why most people thought it should was purely political. But yeah, I gotta agree with your views on Chicago. Good, but not Catch Me if you Can good or LOTR good.
I agree with most of these, but you've got to be kidding on 1958. Auntie Mame, I could watch over and over. But it was clearly Gigi's year, as it swept the awards much like LOTR would 45 years later. And both films deserved to. I do think they're on par with Touch of Evil and better than Vertigo <gasp!>, which gave away its plot twist too early in the film! As for Cat, it's good too, but better than Gigi or Auntie Mame? That's a matter of opinion.
I think American History X was better than Shakespeare in Love.
I think Howard the Duck was better than Shakespeare in Love.
I don't know why people did not mention Gone with The Wind. It is very melodramatic and has simply not stood the test of time. What about The Wizard of Oz or Goodbye, Mr Chips ? They are still breathtaking.
Then again, Hollywood is all glitz , glamour and money. Have you noticed that the more millions you spend on a film , the more Oscars it seems to attract ? In the end the Oscars are superficial. If you are serious rabout recognition for quality film making then look at the Cannes Film Festival.
The majority of moviegoers only recognize Chariots of Fire as “that movie where the guys jog to Vangelis" because the majority of moviegoers haven't seen it. Doesn't sound like you've seen it either. True, there aren't any melting Nazis and the actors have those funny accents but it's still a decent flick. Watch it some time, then form an opinion.
Where did I say I hadn't seen it, Brandon? Don't form an opinion on a reviewer unless you have all the facts of what they have or haven't seen.
I've seen it. It's decent, but not memorable. On Golden Pond or Raiders are just as good, and stood the test of time a lot better. That was the point.
You are being a little unfair though Elisabeth. Raiders is Iconic but it's popularist entertainment.
Chariots of Fire is Iconic. The fact that we still remember the images of the guys running on the beach shows how iconic it is, but it also says something about who we are, and how we have changed. Its about religion and ethics and the will to win. It's about determination and values.
There is nothing wrong with popularist entertainment, we all love it, but I believe the best picture award should go to a film that does more than just make us smile. I was entertained by Raiders, I was entertained and inspired and learnt a little something with Chariots of Fire. That is why I believe it is a more complete picture.
Crash – the best in the weakest year ever at the Oscars.
Titanic – totally agree, even though L.A. Confidential and Good Will Hunting (and perhaps 1-2 others) are also brilliant and would have been worthy winners as well.
The Greatest Show On Earth – have not seen it yet; Singin' in the Rain for me.
Driving Miss Daisy – clearly weaker than Dead Poets Society, which is my pick for that year.
Around The World In 80 Days – personally I think it's at least the most entertaining in yet another quite weak year.
Gigi – Cat On A Hot Tin Roof is huge, one of my all-time favorites, but it just happens that I also adore Gigi and can't really decide between these two; if I were completely objective, I'd probably give it to COAHTR.
Chariots Of Fire – good pick in a very good year with ROTLA and On Golden Pond (especially), at least as good as both of them.
Oliver! – nice little movie but it's nothing compared to The Lion In Winter.
Forrest Gump – great pick in the best year ever for me; obviously The Shawshank Redemption and Pulp Fiction both would have been excellent winners.
Chicago – decent choice in a fairly strong year with The Two Towers being my favorite and The Pianist also being very good.
How Green Was My Valley – I feel very strongly about this and I cannot overstate it: there is NO WAY Citizen Kane should have won over this movie; for me it's like the best decision the Academy ever made; Citizen Kane is, technical brilliance aside, a completely dull, lifeless and inconsequential movie, while HGWMV is just outstanding on every level.
Shakespeare In Love – again, decent choice in a good year; Saving Private Ryan was good, but not BP material; personally I would have gone with La vita e bella.
I really struggle between Forrest Gump and Shawshank. They both deserve it, but on almost all the individual awards you have to give it to Forrest. Tom Hanks' acting is superb and definitely outshines Freeman. The direction of Forrest Gump is just about perfect from Zemekis mixing the footage, creating the different periods in history. Technically its an achievement as good as Cameron's.
If the best picture oscar is a culmination of its parts then Forrest has to get it. If the best picture goes to the most enduring movie it is Shawshank by a nose… perhaps. My heart says Shawshank, but my head says Forrest. I think it's fair.
If I'm really honest I would say that Shawshanks title as best film never to win an oscar is probably one to be proud of, but I totally disagree that Pulp Fiction was in the running at all. If there was a genuine loser, it was Three Colours Red, which barely got a mention in the oscars that year.
I disagree about Crash- I think it deserved to win. I liked Brokeback too, but it wasn’t as deep or as good a film as Crash.
I also disagree about Forrest Gump- it deserved to win.
I agree with you about Driving Miss Daisy- I think Dead Poets Society should have won.
I agree with you about Chicago- LOTR was the best of the nominees.
I definitely agree with you about Titanic- it is one of the most overrated movies of all time.
I loved Crash. I really did. I love the style of all those intertwined stories. Brokeback Mountain was just ok. I kept on thinking if it were a heterosexual couple would this story be worthy, and I just struggled. It was slow and a little dull.
I dont think a movie should necessarily win just because its a taboo subject. Crash on the oher hand felt tight and tense and as I watched I felt more and more uncomfortable at my own personal prejudices. I believe films like Crash and Brokeback Mountain have to make you think. It fails totally if it fails to provoke discussion, I have yet to hear a discussion following Brokeback except the academy didnt give it the gong because it's about homosexuality. Yet crash comes up regularly in discussions about racism.
13. Norman Taurog, Best Director – Skippy (1931)
They'll correct this before 2018.
Dear Ms. Rappe,
I couldn’t agree with you more. Was it something in the water, or what they were smoking! Especially in the fifties.
Back in the ’30′s I think MGM just bought
Oscars (one reason Irene Dunne never won), but the fifties – who knows. I would have chosen Maltese Falcon (oh, yes, Oscars for Bogart and Astor too), Lion in Winter should have been a clean sweep, and ’52 is just beyond belief.
You forgot to mention Katherine Hepburn’s performance in The Philadelphia Story – what a miss by the academy.
Chad in Colorado Springs
I mostly agree with your assessment; however 2 of the films deserve some defense:
When I saw "Crash" back in the Spring of 2005, I told friends that I had just seen the best film of the year and how powerful the story was. I loved "Brokeback" as well but thought that either film was appropriate for the Oscar.
As for "The Greatest Show on Earth"…it was a pretty awesome experience for an 8-year old kid seeing his first movie. Betty Hutton was definitely over the top but Heston did a good job and Gloria Grahame was a hoot! not great; but still fun.
"Oliver" has always been a pet peeve. Over "Lion in Winter" is bad enough…but "2001"? The best revenge was that for not getting nominated, within 10 years the AFI was listing 2001 as one of the 50 best of all times.
You're also right about 1956: I absolutely hated the silly "80 Days"…over The Ten Commandments, Giant, Carousel, The King and I, The Searchers, Bus Stop, La Strada, Lust for Life, Anastasia, Friendly Persuasion, The Brave One…What a Year!
As for Titanic…now with Avatar, James Cameron is starting to make me sick.
I agree Hepburn's Tracy in Philly was great but Ginger's "Kitty Foyle" was so shocking and groundbreaking that she swipped Kate's thunder. Hepburn's performance in 'Summertime' and 'Long Days Journey…' are also Oscar worthy IMO.
Did we seriously need this list? It's a total cliche and completely safe. I saw every film from 2005 prior to the Oscars except for Good Night and Good Luck and I always thought Crash and Capote were the standouts, Crash fully deserved to win.
I wonder how many of the winning films the person who wrote this has even seen, cause this list is the typical "HGWMV didn't deserve it cause Citizen Kane was nominated", "Crash because of Brokeback Mountain", etc. I've seen a great number of the winning films and Cimarron and Going My Way are by far the worst.
Crash was a film about LA, and Hollywood loves movies about itself. It was also a better ensemble picture and dealt with an equally hot issue – racism. Call it a surprise win, but Brokeback Mountain got a lot of other awards which Crash didn't come close to, so it was evenly matched.
Titanic: it was the most expensive movie ever and it MADE money. That got it the award, just as Lord Of The Rings eventually got one — nothing to do with the movie (both were effects, not story).
Driving Miss Daisy won because the Academy now skews older, it has fantastic performances from its leads, and tells a story about a wonderful friendship. Field Of Dreams was also good, but it wasn't saying anything about the human condition other than a love of baseball, which by this point was overdone for Kevin Costner.
GiGi's competition wasn't great: A Touch Of Evil was changed by the studio in a very public row, and Vertigo's use of Panavision instead of Cinemascope cut it out from a lot of viewers. Vertigo is pure Hitchcock, but doesn't stand out from his films — Rear Window is more engaging a performance by Jimmy Stewart, and Psycho would be his ultimate achievement. Throw in the romantic side of Paris and you've got a movie that was clear to win hearts as pure cinema, whereas Hot Tin Roof was a play that already was recognized for its stage production.
Around The World In 80 Days belongs to the days of epic film making. Ten Commandments was its closest competition, but the director won enough already. Giant may be superior now, but in those days it lacked the spectacle that was challenging the new fangled television sets. And there's nothing wrong with the movie: it's still the best interpretation of that literary classic.
Chariots Of Fire won the Academy on its personal victory story, the same was as many films that win focus on one person overcoming great odds to win. Best film? Probably not, but the competition was weak… or recycled, since Indiana Jones was the 30s serials and On Golden Pond another performance by the celebrated.
Oliver! was the last of the great studio pictures. By the 70s, it was about directors, not big spectacles. Lion In Winter was good too, but Oliver! was the one film that had that classic remembrance factor. You can still think of the songs years later. As for 2001, it's a dense film that wasn't Kubrick's best.
Forrest Gump had two things going for it over Pulp Fiction: simple story and a use of special effects that every old person in the Academy could understand. The rest of the competition wasn't even close.
Chicago HAD to win. There was no other competition. Adaptation and The Hours were both slow, and the attention was on the performances of the lead actress versus the story itself. Road To Perdition was based on a comic book and got weak support from the studio. And there was no way Two Towers was going to win because everyone was waiting to finish the trilogy before it got awards (despite it being the best of the three as an actual film!). Catch Me If You Can could have won, but Chicago was more old-style, had big names attached, and Hollywood wanted to celebrate the classic.
How Green Was My Valley is not awkward. It dealt with the struggle of individual lives at a time when America still felt climbing out of the depression. Note also that European voters were basically gone to war by that point too, and the other two films you mention would become a lot more celebrated after the war because of the rise of cinematic studies.
Shakespeare In Love was the moment the Academy lost its credibility. A weak film that was no way better than the rest-of-the-award-winning Saving Private Ryan — it would soon come out that studio advertising got it its award, and from then on in it really became about studio choices rather than strong films.