From left, Torian Miller, Angela Alise, Felonious Munk, Dewayne Perkins, Sonia Denis and Dave Helem in "Black Side of the Moon." (Teresa Castracane)

In a measured, spot-on Barack Obama voice, the actor Felonious Munk soberly surveys the Woolly Mammoth Theatre Company audience and then asks: “[WTF], America?”

Plainly, the six African American performers of the Second City’s “Black Side of the Moon” are keeping their salty material fresh. The opening addresses the startling election results, and a Trump mask is featured in a horror-movie sketch.

The cast isn’t just ripping from the headlines; in up-to-the-minute sketches, songs and stand-up routines, jokes come from all sorts of angles. During a bit explaining his days as a math teacher, Dave Helem recalls a student asking him why the high school wasn’t having a prom.

“I’m like, Dude: You’re 22,” Helem replied.

Helem’s deadpan style is a highlight of the grab-bag show, yet almost everything comes with a cautionary warning. “It’s never just jokes,” we’re told early, and it’s true. Although Helem displays a particular gift for swerving from heavy-hitting topics to sudden whimsy, director Billy Bungeroth’s cast is perfectly willing to be blunt when it hits a red line and figures it’s not really funny anymore. This cast doesn’t flinch from tossing uncomfortable truths at the crowd with a gaze that says, “Deal with it.”

That makes “Black Side” sometimes just plain painful, along with the fact that you can’t always tell whether they’re sticking the landings. The wiry and wired Sonia Denis cuts loose with a scorching diatribe about attitudes toward women; the observations are on point, and Denis’s delivery is commanding. But then do you laugh, or applaud in solidarity? Wednesday night’s crowd tried both. The cues aren’t quite clear.

From left, Torian Miller, Dewayne Perkins, Angela Alise, Torian Miller and Felonious Munk in "Black Side of the Moon." (Teresa Castracane)

Likewise, a skit with an audience volunteer sweeps us back to “the ghost of the [n-word] past,” as the narrator puts it, and the trip is guided by a character named Jacob Bob Marley. As the past becomes the present and future, the role reversal that flips race and privilege is rich — rich enough to make you squirm just a little as a white audience member plays along. Humiliation is not on Second City’s menu — that’s an audience pact that almost no one ever wants to break — but this exercise should be particularly fascinating each night.

For cathartic laughter, Munk’s speech imagining Obama’s inevitably dry, wry farewell is sheer smart delight, and so is the music played by Dewayne Perkins as an aggressive DJ with unexpected taste. Perkins and Torian Miller poke at more stereotypes as a gay couple checking into their old neighborhoods and schools. Angela Alise raps history lessons with a righteous fury that’s as funny as anything all night; the cast feels like a balanced team.

The pace is swift and as quick-changing as usual with Chicago-based Second City’s comic shows, even though the shifting tone kept Woolly’s opening-night crowd off balance. As Woolly artistic director Howard Shalwitz recently wrote, “For escapist entertainment, go elsewhere.” True enough: “Black Side” serves jokes in sync with the moment, but it isn’t offering easy escape.

The Second City’s Black Side of the Moon, directed by Billy Bungeroth. Set and lighting design, Colin K. Bills; sound designer, Julie Nichols; costumes, Robert Croghan. About two hours. Through Jan. 1 at Woolly Mammoth, 641 D St. NW. Tickets: $20-$69. Call 202-393-3939 or visit