meaning having a lot of money, so much so, that one could hypothetically use it to sleep on (as for example, a bed or pillow).
"He got girls AND he sleepin' on the money. Damn."
"Did you hear that he works at the Chicago Tribune now?"
"Shooo, he must be sleepin' on the money!"
"Did you hear that he works at the Chicago Tribune now?"
"Shooo, he must be sleepin' on the money!"
by colleem September 1, 2013