Top Definition
Leon Redbone (b. 1949) is a guitarist and singer whose style focuses on genres from by-gone eras. Mainly, his repetoir consists of songs from vaudeville, old country blues numbers, Tin Pan Alley classics, early jazz (before there was much of a distinction between jazz and blues), ragtime, and various folk songs.

As a musical revivalist, he dresses the part -- usually sporting a fedora, a white suit, dark sunglasses, and a mustache and soul patch. This costume-like persona and his secretiveness have led many to speculate about his true identity. Initially, many thought he was simply another of Andy Kaufman's characters. Others suggested he may be Frank Zappa. David Letterman once proposed that he was Don Novello.

Like fellow musician Mose Allison, Redbone is not well-known outside certain music circles yet has a loyal cult following. Another thing the two artists have in common is a fanbase that consists of legendary songwriters Bob Dylan and Tom Waits. Dylan once said if he started a record lable he would immediately sign Redbone. And fellow revivalist Ramblin' Jack Elliott also expressed being impressed when seeing him perform.

With such giants touting his talents, with his creation of a character no one knows the real orgins of, and with his mastery of interpreting early 20th century American popular music (fusing beautifully the Anthology of American Folk Music with the Great American Songbook), Leon Redbone is one cool mothafucka.
Clueless Guy: Hey, what's that you're listening to now, Mose Allison again?

Me: No. Leon Redbone, bitch.
by Ozarkian July 11, 2010
A near-incomprehensible folk-country singer only popular with people over 50. Listening to Leon Redbone has caused people who listen to non-shitty music to claw at their ears until they pop their eardrums. Listening to him is said to mentally bring you back to the old country farm, where you can see horses being milked.

Yes, horses.
I'd rather listen to panic at the disco! than Leon Redbone. And Panic at the Disco! makes my asshole turn inside out.
by Spontaneous bootay August 16, 2009
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