Madonna takes a jab at Donald Trump while trying out stand-up comedy

Iconic singer Madonna entertained fans at a New York comedy club when she performed a surprise standup gig that stunned many.

The “Material Girl” songstress was in a good mood and took the opportunity to swipe at newly-inaugurated President Donald Trump.

Madonna is known for making waves with her behavior, and she once again caught attention in December by posting a computer-generated picture of herself and Pope Francis in a suggestive position.

The 66-year-old singer embraced her comedic side over the weekend during a visit to the Comedy Cellar. Accompanied by her close pal and comedian, Amy Schumer, Madonna made an unexpected appearance at the comedy club.

Yet, Madonna wasn’t content with just watching the show; she took the stage to try out some new jokes, surprising the intimate crowd of 150 people.

The U.S. Sun obtained a photo of the pop icon dishing out jokes on stage, and an insider told the outlet how she did on the night.

According to the source, the audience was shocked that Madonna was performing before them and took a while to warm up to having her around.

The insider shared, “She was brought to the club by Amy [Schumer]. She did a full 30-minute set.”

Standup comedy is not one of the “Crazy For You” singer’s strongest qualities, but she did her best to entertain the stunned audience with her expletive-ridden jokes.

The source said, “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.”

They added, “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.”

Madonna also had one joke about President Donald Trump up her sleeve. The source revealed, “She also nailed a joke about 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.”

According to the insider, Madonna seemed to be at the comedy club with her boyfriend Akeem Morris and left the venue 10 minutes after her performance.

Meanwhile, Schumer shared a picture of herself and Madonna taken while they were at Comedy Cellar.

The blonde-haired pair wore black outfits in the snap, which showed Madonna trying to peck Schumer on her cheek.

Madonna reposted the picture on her Instagram Stories along with the caption, “Last night was fun!!” and “Thank you @amyschumer.”

She also shared a picture of herself and Morris on her Instagram Stories and tagged him in the post.

This is not the first time the pop diva has performed at the famous comedy club, where she made her standup debut in 2017.

In similar circumstances, she accompanied Schumer, who brought her on stage. The good friends then went ahead to perform together.

A delighted Madonna took to social media afterward to share her excitement about doing standup comedy.

She wrote, “I was tagging along with @amyschumer at @NYCComedyCellar.”

The “Hung Up” crooner added, “Making my standup comedy debut! What a thrill. Finally busted my cherry. Thank you, Amy.”

Although Madonna’s standup comedy skills are not exceptional, she knows how to get people talking with her antics on social media.

She proved this in December 2024 when she shared AI-generated images that showed her posing with the head of the Catholic Church, Pope Francis.

The images showed Madonna in a revealing outfit that exposed her chest area while the Pope wore his usual regalia and had his hands around her waist.

The Pope’s face was close to the singer’s, and he was in a pose that appeared as though he wanted to kiss her.

Madonna’s post sparked mixed reactions online after she shared it, with many calling her actions “disrespectful” and an “insult to Pope Francis.”

The “Like A Prayer” songstress has always been at loggerheads with the Catholic Church, which has criticized her for actions perceived as disrespectful to the religious institution.