How Roy Wood Jr. approached the White House Correspondents’ Dinner
Wood's approach to the WHCD offers wise lessons for all comedians.
How Roy Wood Jr. crushed the toughest room in comedy goes “backstage with the ‘Daily Show’ comic (and next host?) as he worked on Tucker Carlson jokes and navigated the party scene at White House correspondents’ dinner weekend.”
Some great standup tips come through along the way that are true even if you’re performing for a bunch of schmucks eating chicken fingers as opposed to, y’know, the President.
Defend the indefensible.
Wood likes to structure his jokes as counterintuitive defenses of the seemingly indefensible.
Get rid of long setups and jump into the action.
He’s taken to heart the old writer’s trick of jumping directly into the action, ridding his sets of long setups.
“But if we get rid of the Confederate flag, how am I going to know who the dangerous White people are?” is the opening line of his stand-up special “Father Figure.”
“Once you hear … ‘Confederate flag,’” he later explained on comedian Marc Maron’s podcast, “I’ve got your undivided attention.”
Consider carefully if you really want to go after people who are sick, vulnerable, or something else that might make it seem like you’re punching down.
Wood figured Senate Minority Leader Mitch McConnell (R-Ky.), who’d recently had a medical incident, should be off limits. The team discussed several jokes about long-shot 2024 presidential candidate Nikki Haley but concluded that there were too many potential land mines in jabbing at a Republican woman of color.
If it takes too long to explain the premise, skip it.
He played around with a joke about the affair between former “Good Morning America” co-anchors T.J. Holmes and Amy Robach, but it required too much explanation.
Know your audience (and avoid references they won’t get).
They quickly decided that the audience was too White to make a Lori Harvey joke. And the Black journalists in the room would appreciate a joke about the Shade Room, but there probably wouldn’t be enough Black journalists there for it to be worth it…
Put your edgy stuff later in the set once they’ve grown to trust you.
The only possible groaner, a joke about school shootings, clearly worked with the improv audience but, Wood reasoned, needed to come later in Saturday’s set, once the audience had grown to trust him a bit.
Troubleshoot your soul.
“You don’t get to where he is in comedy without troubleshooting your soul, man,” [Tommy] Davidson said. “It’s just too high of a trapeze act. You fall, there ain’t no f---ing net there.”
Meld the mission of truth-telling with the joy of joke-telling.
Now Wood was determined to meld the mission of truth telling with the joy of joke telling. His sets became less observational and more political. Today, he occupies the space filled by Chris Rock in the 1990s and Dave Chappelle in the early 2000s — a Black comedian who doubles as one of our most thoughtful political commentators.
Check out my latest special, “Matt Ruby: Substance,” at YouTube: