Like many people confronted with the cruel reality of homelessness on a night out in the Meatpacking District, Oprah Winfrey reportedly thought she could fake that her purse was empty (really, Oprah?) and have panhandler Julio Bazan be on his way. But that was before she heard his killer material! He joked, "Hey, Oprah, why is it good to date a homeless man? [Because] when you're finished, you can drop him off anywhere!" The joke was so good that Oprah reportedly handed him five $20s through the window of her limo. Bazan says he spent it on booze, underwear and a steak dinner. What, you can think of something better on which to spend it?