2. Lil’ Wayne
Lil’ Wayne doesn’t even try to deny his rampant promiscuity, but what can you expect from someone who lost their virginity at the tender age of 11? He’s also unapologetically boasted about sleeping with Chris Bosh’s wife, Adrienne. Who else has he spent time between the sheets with? Christina Milian, Toya Carter (baby mama), Meagan Good (back in the late 1990s), Nivea, Lauren London (baby mama), Solange, Karrine Steffans (better known in the rap community as “Superhead”), Kat Stacks, Skylar Diggins, and plenty more.