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1.
Getting pinned down while swimming alongside a killer whale in open waters; I fail of immense proportions; Free Willy 3: The Rescue.
"Oh man, did you see that killer whale fall on top of that diver!?"

"Yeah! That was a whale fail!!"

"Almost as whale fail as Keiko in Norway!"

"THEY ATE KEIKO!?"
by Epic Marine Biologist January 21, 2009
 
2.
Describes the action of someone who is overweight doing something very stupid and embarrassing, such as falling down, dropping items, etc.
Matt: Dude, did you see Big Betty fall down the stairs yesterday?
Jim: Hell yeah, total Whale Fail.
by alunajoy September 30, 2010
 
3.
when someone says something that is just so "mind numbingly vile and reprehensible yet stupifyingly unfunny and embarresing" they get something even worse than a "Facepalm" they get a Whale Fail

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Boy: Why do Negro people smell like gorilla feces?

Boy 2: You sir deserve a Whale Fail
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by delusion72 July 07, 2010