Along with impressive résumés, which include stops at the Edinburgh Festival Fringe and multiple jobs at late-night shows (Ms. Friedman worked at “The Daily Show,” where Ms. Wolf is now a correspondent), these comics both seem most comfortable when veering into areas that are decidedly uncomfortable. Their acts do not preach to the converted (they barely touch on Mr. Trump) or traffic in the kind of jokes likely to earn applause.

Ms. Wolf, whose first solo show is “So Brave,” criticizes political correctness as often as Mr. Trump does. “I’m not a pay-for-my-own-drink feminist,” she says. “Everyone has their own line, and mine is at the bar.”

And the title of Ms. Friedman’s show, which has its premiere on Seeso and Amazon on Oct. 20, includes a highly inflammatory gendered obscenity. When telling jokes about abortion and Ebola (an obsession of hers), Ms. Friedman often slowly leans forward, flashing a just-us-friends-here smile, to test how far the audience will tolerate her pitch-black sense of humor. But when she turns to Mrs. Clinton, she adopts a more prosecutorial stance, asking why Americans don’t like this trailblazing politician. After offering suggestions — too insincere, inauthentic — she asks her listeners, who shout out insults like “sellout” and “liar.”

“Americans have more words for why we hate Hillary than Inuits have for snow,” Ms. Friedman says, adding with a deadpan expression that it couldn’t possibly have anything to do with gender. “If only we could gauge American misogyny,” she mock-mused, sarcastically imagining the perfect social experiment that would reveal “what percentage of American democracy would rather have a tweeting asteroid crash into American democracy than a woman leading.”

What Ms. Friedman is arguing, of course, is that Mrs. Clinton is widely disliked because we live in a sexist society, end of story. Even among Democrats, this is the kind of blunt point you often hear in private, but rarely on Sunday-morning television shows. Loudly asserting what most pundits whisper about is one of the finest traditions of political stand-up. And yet, many of Ms. Friedman’s jokes support the idea that Mrs. Clinton is hard to like. “I love her like I love Lady Macbeth,” she says. “I love her like I love any unlikable female protagonist Netflix throws my way.”