Currently engaged in constant resistance to President Donald Trump‘s administration and its aggressive agenda, the Democratic Party and the Left are enduring bleak and uncertain times. And their grim political state of affairs may turn them away from a tool vital to their recovery — a sense of humor.
The controversy surrounding the recent cancellation of Stephen Colbert‘s The Late Show largely ignored that a decade ago, the former Comedy Central star began his CBS 11:30 p.m. time slot career with a traditional, light entertainment hour. Over the years, Colbert’s episodes grew more serious and partisan until the CBS show often seemed more like Ted Koppel’s Nightline than Late Night with David Letterman.
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In 2024, Trump and his running mate, Vice President JD Vance, campaigned (successfully, it turned out) with off-the-cuff attempts at hit-or-miss irreverent wit. Yet Colbert and his anti-Trump sentiment have sought more sociopolitical relevance than laughs.
It begs the question about whether progressives can allow themselves to be funny while being perpetually outraged by Trump. If the Left goes for satirical laughter, is it denying the moment and letting its team down?
Joe DeRosa is a successful stand-up comedian, writer, and director. He watched Colbert wander from a more comedic format toward stronger political and protest content. In the wake of the CBS cancellation, DeRosa said he believes the Left can still have a sense of humor if it doesn’t hamstring itself by restricting speech and available topics.
“I think they can be funny, but the problem is they’re making so many rules about what it is to be funny and what we’re allowed to say,” DeRosa said. “I couldn’t care less what jokes [Colbert] wants to do on his show. If somebody else is offended by a joke, I couldn’t care less about that, either. But, when you start saying what you’re allowed to say [in a joke] politically, you’re painting yourself into a corner.”
DeRosa added that he disagrees with Colbert’s response to the CBS cancellation after he took the show down a more serious path.
“What bothers me is the hypocrisy of it all,” he said. “My biggest issue with the whole Colbert thing right now is: ‘Hey, man! If you think [the cancellation] was truly and only about your perspectives and things that you were saying that were not allowed to be said, I don’t have a problem with you having that opinion or take. But why are you not walking? Walk! Don’t sit there and take more of this blood money.’”
Tammy R. Vigil, Ph.D., responded from the academic world, defending the current progressive ability to crack wise. Vigil, an associate professor of media science at Boston University, insisted there’s enough left-leaning comedy out there unless corporations under political pressure shut it down.
“There are lots of liberals and progressives who are using humor to serve the basic social function of comedy — to criticize the powerful in an accessible manner,” Vigil said. “Sometimes the humor is sarcastic, sometimes satirical, sometimes wry, sometimes clever, and sometimes it falls flat … So, liberals are certainly allowed by the public and their own supporters to be funny.”
Vigil said the cancellation of Colbert is another example of corporate leaders silencing left-wing comedy to “kowtow” to the current presidential administration and is not an isolated incident.
“The Trump administration seems to lack any sense of humor, self-reflection, or understanding of the importance of open criticism, and comedy in a free and open democracy,” she added. “If there is an effort to not allow comedy among liberals and progressives, it seems the strongest attempts have been from the GOP and its leadership.”
John Limon, a professor at Williams College and author of the book Stand-Up Comedy in Theory, agreed with Vigil that pro-Democrat comedy is surviving. Limon pointed to Jon Stewart, John Oliver, and Colbert, a departing host for the next nine months, as champions in the fight against Trump.
“Even someone like Rachel Maddow, though not a professional comedian, inserts humor into her monologues because the troops need to be entertained,” Limon said. “The problem for liberal comedians these days isn’t political correctness. It’s that the object of their attacks isn’t smug high seriousness. It’s tragic buffoonery.”
While Limon insisted that progressives can still “lighten up” even with Trump in office, his comments lean into the brooding sobriety, leading many to question whether left-leaning minds can maintain a sense of humor over the next three years and five months Trump has left in office.
“The problem isn’t the inability of liberals to lighten up,” Limon added. “The problem is in their failure to face the facts seriously. The amount of sheer newsgathering on comedy TV is startling, as is the articulateness of the best comedians in pinpointing the … inconsistency of conservatives who have given up their conservatism for Trumpism.”
Writer Bill Schulz appeared as a regular on Fox News’s Red Eye with Greg Gutfield before becoming the co-host of the Mornin’!!! w Bill & Joanne podcast alongside Joanne Goodhart. He insisted that progressives can’t shift any attempts to humor to a looser, more centrist “vibe” now because it won’t sell.
“I don’t think it really matters if the leftist tone of most late-night hosts, for example, tones down the preaching,” Schulz said. “The audiences they have are the audiences they want. Changing their tune isn’t going to get a more right-leaning demo to give them a try.”
Rather than focus on complicit conservatives or humorless progressives, Schulz said he longs for comics, writers, and TV personalities to open up satirical attacks on all fronts. Whether looking at South Park in the United States or the puppet-driven Spitting Image in the United Kingdom, it’s still possible for comedy shows to attack the Right and Left flanks simultaneously. Yet the partisan tribalism of American culture makes more examples hard to find.
“Most good comedy still has both guns blazing,” Schulz added. “That’s still more a trait via left-leaning comics than right-leaning ones. I guess my only examples of thoroughly conservative comic voices (although there are plenty of good stand-ups out there that lean right) came during my time at Fox News. It already astounded me how impossible it was to even remotely criticize their side back then. We see the same from the left now.”
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Even if progressives find a way to unclutch their pearls during Trump’s final term, Schulz said he sees the format that political late shows and other progressive news commentary use as antiquated, as both the concept and acceptance of “woke” declines.
“I think the whole woke thing is already course correcting,” Schulz said. “As a slightly disinterested observer, I’ve noticed the pendulum swinging back toward the idea of most people, places, and things being fair game.”
John Scott Lewinski, MFA, is a writer based in Milwaukee.