Damon Williams on "Getting Paid to Practice" Comedy

The holiday season is a time long considered to be for family. With all the awkward gatherings, fattening food, and tireless fielding of inappropriate questions from people we're obligated to see once a year, Christmastime can be overwhelming and far from funny.

But this year, when Santa leaves and takes his Christmas cheer (or cynicism) with him, Red Grant and Damon Williams are coming to town. They bring with them the gift of laughter, presenting the perfect opportunity to indulge in two well-needed drinks (the standard comedy-club minimum).

And, sticking with the holiday theme, it's almost like comedian Damon Williams is family.

"When you do radio, psychologically you become almost like family," says Williams, who has a weekly connection to the South Florida market as a regular on the popular syndicated Tom Joyner Morning Show, which airs on the local R&B station Hot 105 (WHQT-FM). His segment is called "Seriously Ignorant News."

Spending his holiday here in South Florida, Williams gives us the chance to take a break from our families and to instead hurt our faces laughing with him — a reference to the #HurtYaFaceFunny tag the comedian uses on all his social media.

"This is the only art form you can get paid to practice and learn."

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Williams' name might not be as familiar as say, Kevin Hart's, whose sold-out Fort Lauderdale show is the reason promoters decided to bump Williams to the Palm Beach venue. But on the same day, about the same time, in an improv club just a little farther north, Damon Williams wants you to laugh so hard that your face literally hurts.

The Chicago-based comedian and actor cut his teeth at All Jokes Aside, the preeminent black comedy club of the '90s, and over the past two decades, he's appeared on TV shows like Comedy Central's Premium Blend and HBO's Def Comedy Jam and was also the opening act for the Kings of Comedy Tour. Unsurprisingly, he cites all four Kings of Comedy (Steve Harvey, D.L. Hughley, Cedric the Entertainer, and Bernie Mac) as among his direct influences, along with the undisputed greatest standup of all time, the late Richard Pryor.

But it was Eddie Murphy's Delirious, watched repeatedly on VHS back in the day, that was the game-changer for Williams. "We had heard Richard Pryor and imagined it, but Eddie was on video. Eddie took it to the next level."

Williams notes that in the '90s, urban-themed comedy clubs and TV shows like Def Comedy Jam helped create opportunities for young comics like himself. And from there, the opportunities kept coming.

Yet there's one thing people never seem to ask him: What's the money like?

"I read a Playboy article way before I started — and yes, I actually read it," he tells New Times. "It said comedians can make six figures and be under the radar and not be a household name, and I concur. People are very unaware that as a standup comic, if you have a good reputation and do good work, there are so many different avenues to earn."

From college gigs to game shows, hosting events, and satellite radio residuals, Williams says comedy can be quite lucrative, even when starting out.

"This is the only art form you can get paid to practice and learn," he says. "That's what I did — I learned the business first. This is a very good business if you do it properly." And he seems to be doing it properly. Williams travels internationally, works constantly, and says he hasn't had a conventional job in 23 years.

For the fourth year in a row, Williams will bring his fast-paced comedy to South Florida. He once teased his audience, saying if they didn't catch his last joke, they probably needed to get their GED.

"It's a rapid-fire style with very few lapses or pauses in laughter," he says. "A lot of comics are storytellers and go into detail and get stuck on nuances. I move on pretty quick because I grew up in the era of ComicView and snippet comedy."

Williams explained that with BET's ComicView running "Best of..." shows, the best way to get included in the clips — and the best way to be seen — was to have shorter jokes. Another factor contributing to his quick tempo is his experience as a spontaneous and interactive host.

But while his material is usually quite universal, lately Williams has been touching more on personal life and current events. It's hard for him not to talk about his family and current relationship: His New Year's Eve wedding is around the corner, and he'll be going on his honeymoon right after his shows here in South Florida.

The timing is perfect too. Not only will the couple escape the brutal Chicago winter but New Year's Eve holds particular significance for Williams and his fiancée — that's when he proposed. Leading up to the moment he got down on one knee, Williams made a series of relationship jokes to a live audience. He then called his leading lady out on to the stage, and as she figured out what was happening, she hid her face in her hands. Perhaps she was a bit embarrassed that this sweet and tender moment was unfolding in public, or perhaps her cheeks hurt from laughing so hard, because it was hilarious.

Regarding politics in his jokes, especially with Donald Trump and Ben Carson follies in the news all the time, the comic says there's just so much material.

"I have a way of slipping in a message or at least touching on certain topics while people are in the course of laughter," he says. "But you don't wanna be too heavy-handed with it, especially with a mixed crowd, because not everyone is going to share your viewpoint."

And that's what identifies his style of comedy — Williams gives himself room to not be politically correct while still being political.

"My whole motivation is laughter," he says. "My motto is: 'Laugh tonight — we can be serious tomorrow.' "

Red Grant With Special Guest Damon Williams
7 p.m. Saturday, December 26, at the Palm Beach Improv, 550 S. Rosemary Ave., West Palm Beach. Tickets cost $20 plus fees via palmbeach.improv.com. Call 561-833-1812.