The Song: 2009's "A Night Off," by Drake
The Highest Charting Position: N/A
Raise your hand if you're saying, "That's right! Lloyd was on So Far Gone!" right now. You're not alone. We forgot all about Young Lloyd's contribution to Drake's seminal mixtape until we sat down to put this list together. But that's more a representation of how good SFG was. Next to one of the hottest crooners at the time, Lloyd more than holds his own.