Biggest Oscar flub
 

I know the biggies are Annie Hall over Star Wars, Tomei for Vinnie, Shakespeare in Love.

But I was listening to Trey and Matt on Fresh Air w/ Terry Gross, and it reminded me of Blame Canada losing to that Phil Collins song, rep to the first who can recall it's name and/or the movie it came from.

And it's not like it was a total outsider exercise, the co-writer with Matt and Trey was Marc Shaiman, who has five nominations, has authored [I believe] every one of Billy Crystal's opening numbers [ie, iiittttts, a wonderful night for Oscar . . . Oscar Oscar. . . ], and has been musical director for the Oscars more than once.

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The time Jethro Tull won over Metallica

I'd probably like the song better if I could understand more than 25 percent of the lyrics.

Can You Feel The Love Tonight from Tarzan

Right movie, wrong song.

Strangers Like Me!?!?!?!!

You'll Be In My Heart!!!!!!!!!!!!!!!!!!

"You'll be in my heart" from Tarzan??!!

Star Wars was not theater that the Oscar voters would ever like.

Oopsies that's from Lion King

Biggest Oscar flub? Dr. Strangelove losing Best Picture to The Sound of Music.

Strangers in the Night by Sinatra.

I've got to nominate "Goodfellas" losing to "Dances with Wolves"

This times infinity +1

Re: Goodfellas v Dances and Strangelove v SoM, at least in those instances, both movies were very good. Those choices suffer more from apples and oranges than anything else. Certainly, for SoM it has endured as more of an all-time cinematic classic, with Strangelove being perhaps superior in some aspects, but more of a niche product. Goodfellas v. Dances was a clash of the titans type of deal, it's tough to say, given their respective careers that Costner's masterpiece tops Scorsese's, but just comparing the two films I can make a case for either. All four are somewhere in my top 30 of all time.