In "Tom Traubert Blues" (Tom Waits) it's about drinking till death.
and you can ask any sailor
and the keys from the jailer
and the old men in wheelchairs know
that Matilda's the defendant, she killed about a hundred
and she follows wherever you may go
waltzing Matilda, waltzing Matilda, you'll go waltzing
Matilda with me
by Squarlin November 25, 2015
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A phrase used to describe having sexual relations with a homeless person or "hobo." The phrase originated from an Australian Folk Song of the same name, which tells the story of a lonely "swagman" (a man who travels the country on foot looking for work) who carries all his belongings in a "Matilda" (a particular term for a bag). He sings affectionately to his Matilda because it is the only company he has.
Man, you were trashed last night. You committed a Waltzing Matilda.
by The Tortoise and The Kare October 1, 2010
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