18. Waka Flocka Flame
Waka Flocka Flame is one of the strangest celebrities on this list, but he actually ran for president in 2016. The campaign seemed like a joke for many reasons (one of which is that Waka Flocka Flame is only 28), but he did release two campaign videos, and it was a boost to his career. There’s a good chance he’ll pull the stunt again in 2020.