Ask A Genius 1474: Bombed Jokes, Trump Roasts, and Comedy’s Unintended Consequences
Author(s): Scott Douglas Jacobsen
Publication (Outlet/Website): Ask A Genius
Publication Date (yyyy/mm/dd): 2025/08/07
Scott Douglas Jacobsen interviews Rick Rosner about his most painful joke failure at the Grammys and the far-reaching impact of comedy, including Trump’s infamous roast at the 2011 White House Correspondents’ Dinner. Rosner reflects on his career highlights, awards, and the unpredictable power of political humor.
Scott Douglas Jacobsen: If you could ask a former comedy writer for Jimmy Kimmel one question, what would it be? What’s the one question you’d ask a former comedy writer for Jimmy Kimmel? Did you win or get nominated for any major awards?
Rick Rosner: I got nominated for an Emmy. I won a Writers Guild Award.
Jacobsen: So, what’s the most painful joke you’ve told—or heard—that completely bombed?
Rosner: Alright. So, my writing partner and I got hired one year ago to write for Jon Stewart when he hosted the Grammys. Jimmy [Kimmel] was writing for him, and he brought us in to help with the script.
I pitched a joke about the William Morris logo—it’s a W superimposed on an M. I said it looked like the label on a jug of moonshine, like the four Xs you’d see in cartoons or hillbilly culture. Back when people leaned into that yokel-from-Kentucky image, the symbol for a jug of moonshine was X-X-X-X.
Jacobsen: So it’s a layered visual gag.
Rosner: Exactly. Jon Stewart liked it. It tickled him enough that he used it in the monologue. He went out there and delivered it—2,000 people in the auditorium, every prominent figure in the music industry—and not a single person laughed—dead silence.
Jacobsen: Brutal.
Rosner: I didn’t blame the joke. The Grammys audience isn’t a comedy audience. They’re there for the music. They want to see stars, not hear a writer’s cerebral moonshine joke. So, trying to get laughs at the Grammys is a doomed enterprise. But that’s one of the most painful joke failures of my life.
Jacobsen: Oof.
Rosner: Also, the most painful failed joke for the entire world. So, the jokes that hurt the world the most were probably the ones made about Donald Trump by Seth Meyers and President Obama at the White House Correspondents’ Dinner in 2011.
Here’s the background. Obama was elected in 2008. Around that time, Trump—who’s a well-documented racist—became a leading voice in the “birther” movement. That movement claimed Obama wasn’t born in the U.S., that he was secretly born in Kenya, and therefore wasn’t eligible to be president. It was thoroughly debunked, but Trump pushed it for years.
So, at the White House Correspondents’ Dinner—where the sitting president attends and a comedian hosts—they invited journalists, celebrities, and Trump was in the audience. Obama and Seth Meyers roasted Trump. And Trump hated it.
From what people say, that night planted the seed of revenge in Trump’s mind. He decided to run for president to get back at the people who humiliated him. That eventually led to eight years of Trumpism—an era where he’s done a lot to dismantle American institutions. He doesn’t seem to care what he breaks.
Jacobsen: And you were part of that roast?
Rosner: Not that one. But another year, my boss, Jimmy Kimmel, hosted the dinner. Trump was in the audience again. I wrote a joke at his expense—it was lame, probably didn’t even get a laugh. But maybe, just maybe, I contributed to the problem.
Jacobsen: He doesn’t go to those anymore, does he?
Rosner: No. He knows he’ll be made fun of, so he stays away. And, technically, as my wife reminds me, late-night writers aren’t supposed to take credit for specific jokes. All the jokes belong to the show. But still… the end.
Jacobsen: The end. That was good.
Last updated May 3, 2025. These terms govern all In-Sight Publishing content—past, present, and future—and supersede any prior notices. In-Sight Publishing by Scott Douglas Jacobsen is licensed under a Creative Commons BY‑NC‑ND 4.0; © In-Sight Publishing by Scott Douglas Jacobsen 2012–Present. All trademarks, performances, databases & branding are owned by their rights holders; no use without permission. Unauthorized copying, modification, framing or public communication is prohibited. External links are not endorsed. Cookies & tracking require consent, and data processing complies with PIPEDA & GDPR; no data from children < 13 (COPPA). Content meets WCAG 2.1 AA under the Accessible Canada Act & is preserved in open archival formats with backups. Excerpts & links require full credit & hyperlink; limited quoting under fair-dealing & fair-use. All content is informational; no liability for errors or omissions: Feedback welcome, and verified errors corrected promptly. For permissions or DMCA notices, email: scott.jacobsen2025@gmail.com. Site use is governed by BC laws; content is “as‑is,” liability limited, users indemnify us; moral, performers’ & database sui generis rights reserved.
In-Sight Publishing 