Roy Wood Jr. Takes on Leonardo DiCaprio’s ‘N-Word’ Acting in First Look at New Special

When Roy Wood Jr. appeared on The Last Laugh podcast earlier this year, he teased that he would be “closing the window” between taping and air for his next stand-up special. Inspired by the fast turnaround of Dave Chappelle’s 8:46 set, he was eager to get his new hour out into the world with as little delay as possible.

Now, he’s done it, filming Imperfect Messenger at the Gothic Theatre in Englewood, Colorado, less than two weeks before it’s set to premiere on Comedy Central this Friday, October 29 at 10:30 p.m.

And the longtime Daily Show correspondent includes plenty of material about current events in the new hour. But in this exclusive first look at the special, he looks back at Django Unchained and other films that have found white movie stars in the unenviable position of having to scream the “n-word” at their Black co-stars.

“You know one white ally that goes unsung in my opinion?” Wood asks his audience. “Evil white actors in civil rights movies.” As he explains it, if you want to show the “truth” in these films, then you have to include the “heinous shit.” And of course, that burden falls on white actors, who have to “walk on set all nice and then just turn on the racism.”

Over the next several minutes, Wood masterfully plays out the peril of white actors who do take after racist take for hours on end. And there has perhaps been no more “heinous” enslaving character than Leonardo DiCaprio’s Calvin Candie in Quentin Tarantino’s Django Unchained.

It Took ‘The Daily Show’s’ Roy Wood Jr. 20 Years to Get This Good

“That’s one of the bravest white allies I’ve ever seen in my life!” Wood says, heaping ironic praise on DiCaprio for calling Jamie Foxx the “n-word” to his face in front of Samuel L. Jackson. “Tom Cruise does his own stunts?!” he exclaims. “Well, so does Leonardo DiCaprio!”

Wood closes out the bit by joking that DiCaprio’s “sacrifice” was so great in that 2012 film that it would be almost a decade before he shared the screen with a Black co-star again, adding, “If anybody knows Leo, tell him he can come home.”

For more, listen to Roy Wood Jr. on The Last Laugh podcast.

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