Bill Maher Snags Karoline Leavitt Interview for ‘Real Time’: When Show Will Air & More

Martin Holmes October 22, 2026, 9:37 am

Bill Maher and Karoline Leavitt — Real Time YouTube; SAUL LOEB / AFP via Getty Images

What To Know

Karoline Leavitt will make her first late-night appearance on Real Time with Bill Maher.
Leavitt, who resigned as press secretary in August 2026, was frequently mocked by Maher during her tenure.
Maher is also expected to discuss his recent dinner with Donald Trump.

Bill Maher is gearing up for a major episode of Real Time this Friday (October 23), where he’ll discuss his second dinner with President Donald Trump and welcome Karoline Leavitt for her first-ever late-night interview.

Leavitt has often been the butt of late-night jokes, but her upcoming Real Time appearance will mark her first sit-down interview on a late-night show. She stepped down as White House press secretary in late August to spend more time with her family after welcoming her second child on May 1, 2026, with her husband, Nicholas Riccio.

Maher himself has joked about Leavitt on his show during her tenure as Trump’s press secretary. In November 2025, the comedian touched on her response to the president telling Bloomberg News reporter Catherine Lucey, “Quiet, piggy.”

“At the press conference the next day, his press secretary Karoline Leavitt spun this by saying: ‘It’s actually admirable. It’s the President being frank and open and honest. That’s good,'” Maher said on his show, adding, “Well, in that case, ‘Shut up, b**ch!'”

And earlier this year, Maher mocked Leavitt’s defense of Trump sharing (and later deleting) a video that depicted Barack and Michelle Obama as apes. “[Leavitt] said the president was just reposting a meme of him as the king of the jungle with Democrats as characters from The Lion King… as world leaders do,” Maher joked.

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Leavitt was replaced as press secretary by legal pundit Katie Zacharia, who lasted just five days on the job. Zacharia was ousted after a disastrous debut press briefing and accusations that she lied about her legal qualifications. Maher is sure to ask Leavitt for her thoughts on that entire situation on Friday’s show.

In addition to the Leavitt interview, Maher is expected to address his recent dinner with the president. The Club Random podcast host returned to the White House last Thursday (October 15) for dinner with Trump, Stephen A. Smith, and Kid Rock. Maher previously faced backlash after accepting a dinner invitation from Trump in early 2025.

“It was a great dinner. It was a very informative dinner,” Trump said last week when speaking with reporters. “Smart people. Stephen A. is great. Bill Maher, I tell you what, he likes me a lot more than people understand. And I actually like him. It was a good dinner. We talked about everything.”

Real Time With Bill Maher, Fridays at 10/9c, HBO