Bill Littlefield vs Charles Osgood
Izzambic Pizztameter
Dice Clay vs Slim Shady
Jack & Jill meets Bonnie & Clyde
Old Kid n Play vs Old Kriss Kross
Grand Mack Daddies
Young Dana vs Young Marguerite
Phenomenal Women
Nipsy Russell vs Gilbert Gottfried
Dan Rather vs Roy Blount, Jr.The Thrilla in Vanilla
Bad-Ass Dan, Chicago 68
Speaking of Chicago 68, this has also always been a favorite of mine. Listen carefully to hear Buckley call Vidal a "Queer."
I know it may be "too soon" to say this, but I had always wondered about a rap battle betwen Billy Mays and Robin Leach.
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