Madonna jokes about Trump not having "any staff left" if he continues mass deportations during stand-up at a New York comedy club

Last Saturday, on January 25, 2025, Madonna took to the stage at New York's Comedy Cellar, as the singer accompanied her close friend, comedian Amy Schumer. On Monday, January 27, an insider at the comedy club told The Sun that the Frozen singer did a full 30-minute comedy set, adding:

"She did well enough, but the audience was so stunned it was Madonna that it took them the entire set to warm up to her. She didn't do as well as you'd think she would, she got laughs every time she dropped F-bomb, because just hearing Madonna curse is funny."

The insider also told the news outlet of a Trump-related joke the 66-year-old shared at the comedy club, saying:

"She also nailed a joke about how with all of these Trump deportations she's not going to have any staff left, which got some laughs, but really everyone was just so shocked she was there."

Per the source, the Human Nature singer left the club 10 minutes after her performance.

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Madonna has performed stand-up at the Comedy Cellar once before

Madonna's gig at the Comedy Cellar last week wasn't the first-time. Eight years ago, the Physical Attraction singer had taken the stage. Amy Schumer, who was her companion at the club in 2017 as well, brought the Queen of Pop on the stage at the time. The Hung Up singer's set marked her stand-up debut.

Per Billboard, another time the singing sensation put her comic skills on display was on Jimmy Fallon's The Tonight Show in 2015. In that episode, the star called herself a "closeted comedian," and then joked about her tendency to date "younger men" and her Andy Warhol paintings collection.

Schumer later posted a selfie with the 66-year-old from the club on Instagram. Their table had a note - visible in the picture - that read:

"This table is reserved for Comedy Cellar comedians only."

Later, when Amy was invited to The Howard Stern Show, she spoke about bringing the Gambler singer on stage and watching her perform, saying:

"She has something in her that’s like interested in stand-up and she knows that, like anything else, you have to work really hard on it."

Further revealing details about their 2017 stint, Schumer continued:

"She’s like, ‘I want to get up. I’ve got things I want to express'. She goes up with a notebook and she is like, kind of working on her set and it’s not cringey. She’s funny! She’s got jokes. She’s got things to say. She’s got tea."

The I'll Remember singer's comic outing in January comes eight months after the singer wrapped up her twelfth concert, The Celebration Tour. The tour, which kicked off on October 2023, lasted eight months, seeing the 66-year-old traveling across Europe, and North and South America.

It ended in Rio de Janeiro, Brazil, on May 4, 2024. The tour went on to become one of the fastest-selling concert tours and supported the release of her 2022 remix album, titled Finally Enough Love: 50 Number Ones.

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Madonna's boyfriend, Akeem Morris, joined her to catch her comedy gig last week

The Sun reports that Madonna was also joined by her boyfriend, Akeem Morris, at the comedy club last week. Morris - a soccer player 37 years younger than her - has been dating the God Control singer for six months. Per the news outlet, the couple first made a public appearance together in July 2024.

A source told The Sun about their relationship:

"Madonna is happier than she has been in a long time. Her romance with Akeem has been a real whirlwind but they are so in love."

The couple also spent a holiday together last year, where they were joined by all six of the Secret singer's children.

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Madonna has been married twice before dating Morris - once to Sean Penn (1985-1989) and then to director guy Ritchie (2000-2008).