Jimmy Fallon: We were in your dressing room backstage on SNL.
Justin Timberlake: We were just shooting the shit, right?
Jimmy Fallon: You were coming on my show later that week, and I asked, “What do you want to do?” We both thought, well we could sing something. I wanted to do Toto’s “Africa."We could sing that song really well together.
Justin Timberlake: We should still do it! We should do Toto’s “Africa” but we should do it as characters.
Jimmy Fallon: I was thinking we’d do “Africa” as me and you at the age of thirteen. We’d be best friends and have a tape of us having a sleepover and singing “Africa.” We can wear wigs and braces .
Justin Timberlake: We were sitting there, and I said, “Do you remember that guy who did the history of dance?” He did every song that had a dance or was named after a dance. It was a viral sensation. Then we just started kicking around medley ideas. Jimmy was like, “What if we did the whole history of all hip-hop and fit in as many songs as we can?
Jimmy Fallon: We started improvising right there. We went from Jay-Z to “The Humpty Dance” to “How about this one?”
Justin Timberlake: Jimmy’s a great impressionist and that’s what makes it funny—Jimmy Fallon impersonating greats like Snoop and Notorious B.I.G. And, of course, the Roots. If I had the Roots on my show I’d be doing songs every day. Can you imagine if you had a total karaoke session with the Roots? By the way, you should have audience participation karaoke.
Jimmy Fallon: That’s a good idea. I’m writing it down.
Justin Timberlake: You should try to stump the Roots! Have random audience members come up and make requests. Is there a song they can’t play? They can play anything.
Jimmy Fallon: I think why those videos have gone so viral is partly because everyone knows and loves those songs. That alone is pretty cool. But when you have Justin Timberlake doing it, it makes it insanely cool. After we did the first “History of Rap,” we were on the phone and you were like “I’m in France now and it’s on the front page!” Le History of le Hip Hop. I was so excited, like “Dude. They know who I am in France?” And Justin just goes, “No.” Oh, of course. You’re Justin Timberlake. That’s why this is a huge hit.