Origin of Phrases - L
Lucky stiff
Meaning: To be very lucky.
Example: You won $1000 in the Lotto, you lucky stiff.
Origin: "Stiff" is defined as an ordinary person, an average Joe, even a failure or flop. A "lucky stiff" then is an average Joe who got lucky. The suggestion here is that the person was undeserving and unworthy, just lucky.