The Song: 2005's "Caught Up," by Ja Rule
The Highest Charting Position: No. 65 on the U.S. Billboard Hot R&B/Hip-Hop Songs chart
You have to think that if Lloyd hadn't come out in 2004—a couple of years after 50 Cent ended Rule's run at the top of the charts—these two would have collaborated way more often and been on a string of hit singles together. Instead, we had to settle for this, one of the last single-worthy tracks created by Ja. And Lloyd definitely played a large part in that.