#5. Cassidy vs Freeway
Why it's memorable: An up-and-coming Cassidy rips an already famous Freeway.
Best line: "Throw on a beat." (Freeway)
Complex says: Cassidy earned his stripes battling dudes in Philly, but he gained street fame from destroying Freeway in this lopsided battle. Free's mistake was agreeing to battle acapella since everyone knows his delivery works best over a hard hitting beat. Which is probably why by the end of it, he was begging for one. Cassidy would later boast about the battle on his second album saying, "The punchlines I put on the street/Even made Freeway say, 'Put on a beat.'"