Origins:
There are a couple of conflicting reports as to exactly how the phrase came to be, however general consensus agrees that it was during the Burlesque era (1940s - 1950s) from a popular comedy act (though I've been unable to find specifics on which comedy act).
One of the theories is that the best comedian (the one with the punch line) would be presented with a banana (perhaps as a visual cue for the audience).
The second theory follows "The lead comic in a burlesque show was referred to as the "top banana," and his sidekicks were known as the second, third, etc. – supposedly because they would resort to slipping on banana peels in order to get a laugh."
Interestingly this is believed to of lead to comedians being known (in early show business slang) as bananas.
My preferred theory
A lesser known theory (but one which sounds more legitimate) is: during the 1930's the phrase 'banana' was used as slang for "nuts" (as in crazy). Comedians in the burlesque era specialising in slapstick comedy, allowing for the evolution of:
Crazy comedians -> They're nuts! -> They're banana's -> he's the Top Banana.
Today the saying has dropped the crazy & comedian meanings, and is being used to just mean top/best.
References:
Ed: New theory found (which I prefer)
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