“Everybody has their own time for doing things, and I just have a different, kind of weird road,” Wayans says.
Wayans was thrust into the entertainment business as a teenager, and while he had no formal comedy training then, he watched various members of his family — namely his brothers Damon and Keenan Ivory Wayans — grow as artists. He began working on “In Living Color” with his brothers in the early 1990s and partnered with his brother Shawn on a number of other movie and television projects. And in the past few years, he has branched out on his own.
“As much as I’ve done, I just want to get better. I want to be the best me, and I don’t want to skip steps,” Wayans says. “I started [stand-up] from the bottom and worked my way back up to see what type of artist developed.”
The result is “Woke-ish,” just over an hour of bits that range from the political to the personal. Before putting the special together, he workshopped jokes in smaller clubs, trimming down over seven hours of material. He toured the South to test out material about Donald Trump and Barack Obama because, he says, “if I was going to do a Trump joke, I needed the Trump supporters to be laughing the loudest.” But he also wanted to see how bits about the LGBTQ+ community would play, as well: In the special he tells a story about his daughter being attracted to girls.
“I had certain themes I wanted to talk about,” Wayans says. “I had to find the right combination of stories. You want to make sure you spread it out and have a little bit for everybody, not let the scale tip one side or the other.”
While humor can be found in every topic, he says it’s most important to take the time to decide the proper approach. “As comedians we have to have the freedom to explore,” he explains.
For Wayans, the key to creating the special was to take something topical — like the politics of Trump versus Obama — and make it evergreen so that it would be relatable to a wider range of audiences. “It’s intended to make people think, to make people feel, to make people see things from a different perspective and to unite people through laughter,” he says. “We may not always agree, but if I get you to laugh at least you’ll understand what I’m saying.”
He compares his approach to Bugs Bunny, who he calls “one of the greatest comedians of all time”: “He did characters, he was animated, he was political, he was silly, he was dark,” he says. “I’m a Looney Tunes baby, so I hope this is something [that] will transcend age, race, culture, and just be funny.”
And while he says he is “not afraid to go into dark tunnels and come out with a piece of light” when constructing jokes, he is cautious about how and where he tests them.
