10. Le1f - Wut
Not only does Le1f’s performance in his home-town of Manhattan entertain at a high level with dancers and live instrumentation, but it is also a triumph in television in hip-hop. With Le1f’s late night debut in March of 2014, he became the first openly gay hip-hop recording artist to perform on television. Performing "Wut," the rapper/producer joins in on choreography and never misses a beat or loses his flow - all while wearing a denim skirt and Nike moonboots that Letterman himself envies.