How to Host Awards Shows (and Roast Joe Biden)

EPISODE 55: Inside the mind of Roy Wood Jr.

Roy Wood Jr. is a strategist.

Which is not to say that he isn’t naturally funny. And that the road that brought Roy into these well-appointed rooms — The Daily Show, and the White House Correspondents Dinner, and a seemingly endless series of awards shows — isn’t absurd and winding. (He very seriously considered becoming a baseball umpire, I found out.)

But Roy’s ability to dissect why he got onstage and said something… and how he figured out how to warm up people he was simultaneously insulting… is why I wanted to talk to him in the first place.

Which is not to say that Roy’s won over every room.

The job he wanted most — host of The Daily Show, replacing Trevor Noah — was not offered to him by Comedy Central. And so, a couple months ago, Roy unilaterally decided to leave his job as correspondent.

And all of that, as you’ll see, was strategic, too.

DKN/YOUTUBE SPOILER ALERT:

#AllCommunitiesMatter,

Pablo