Okay, is it us, or are these recent Chelsea Handler and 50 Cent spottings just about the weirdest thing? Handler, comedian/host of E!'s "Chelsea Lately," is known for crushing hard on our most famous rough-around-the-edges rappers, and apparently rapper Curtis "50 Cent" Jackson fits the bill. Are they working on project? Dating? Who knows? Either way, this isn't the first time celebs have left us scratching our heads. Check out the other celeb pairings that at the time -- some even to this day -- seem most odd.