Station: KMEL/Power 106 DJ: Sway & Tech Best Punchline: "I know that my mustache is dirty/But I'm 20, and with this, chicks think that I'm 30." (Eydea)
If skills sold, truth be told, the late-great Eydea would've been a rich and successful mainstream artist. But much like many of hip-hop's greatest freestyle rappers, he couldn't translate those skills into mainstream success.
Both Eydea and Slug were part of a small group of rappers who actually freestyle off the dome—something of a lost art nowadays. These two kids from Minnesota went back and forth for over eight minutes on The Wake Up Show, all while cracking jokes on each other and arguing about show dough.