This is gonna be a long rant into the void, but I don't care.
So I'm convinced that generally speaking the Academy awards the best original song without thinking about trends and future but to the film. So anyway, looking at some winners for best original song and considering who should have won.
2021 - No Time to Die wins the award, Bond songs cleanup at the oscars, but this came out the same year as Encanto. Ignoring the fact the song nominated (Dos Oruguitas) isn't the song everyone was signing from Encanto, but any song from that film is infinitely better and more remember than No Time to Die. I couldn't hum/sing that song if I tried and I've heard it a dozen times.
2016 - La La Land won the best song and was nominated twice, there isn't a memorable song from the film, same year Moana came out with multiple bangers, there was the pop charts crossover hit in Can't Stop the Feeling. La La Land was hollywood masturbatory **** and they cleaned up with it.
2014 - Selma's Glory won, and it's a fine song, but it came out the same year as Everything is Awesome which still slaps, and I'm Gonna Miss you from Glen Campbell: I'll be Me. I think this is another example like La La Land where the movie was why the song won.
2009 - I love Crazy Heart, but nothing is truly memorable about it's song that won, compare that to Princess and the Frog, which would have given Randy NEwman a deserved win.
1998 - What if I told you that a song from Prince of Egypt beat out That'll DO from Babe: Pig in the City or more importantly I don't want to Miss a Thing. A song people still sing 25+ years later.
1992 - I adore Aladdin, but for I Will Always Love You to not be nominated much less not winning despite it being considered one of the all time greatest movie songs of all time is a big loss.
1990 - This one I'm probably all alone, but how did a song from Dick Tracy beat the Jersey Masterpiece Blaze of Glory?
1982 - While not a bad choice, how does the sop that is Up Where We Belong beat of the clearly iconic Eye of the Tiger? HOW?
1980 - Fame beats 9 to 5. That's all you need ot know. .
1979 - If I told you Rainbow Connection didn't win the award you'd think the song that did would be amazing, can any of the old heads tell me if It Goes Like it Goes slapped back in the day, Cause I gave it a listen through and it blows a big one.
1978 - Probably a more personal one, A Star is BOrn wins in the same year we get one of the most iconic film themes of all time that didn't come from John Williams when Bill Conti gaves us Gonna Fly Now.
1967 - The Bare Necessities doesn't win, instead Talk to the ANimals from Dr. Doolittle does.
Like the list of wrong songs winning, is way too long for me. And sometimes it's pretty obvious to me.