Madonna trying standup is no joke: she’s a natural comedian and genuine kook

New York’s famed Comedy Cellar has long been known as a testing ground for hot young talent. The Greenwich Village club hosted stand-ups like Ray Romano and Jon Stewart early in their careers, and although tourists now flock to the venue in the hope of seeing an A-lister do a surprise drop-in, young comics can still get their start there. Case in point: last weekend, Madonna did a set at the Comedy Cellar. You may be able to draw nearly 2 million people to Rio’s Copacabana beach for a concert, but in the cutthroat world of comedy, you still have to start from the bottom.

A report in the Sun said that Madonna tested out material for about 30 minutes, and that she was accompanied to the club by her friend Amy Schumer, who later went on Howard Stern to big up Madonna’s act. “She has something in her that’s interested in standup and she knows that, like anything else, you have to work really hard on it. She is kind of working on her set and it’s not cringey,” Schumer told Stern. “She’s funny! She’s got jokes. She’s got things to say. She’s got tea.”

This news was, like most news about Madonna, met with derision and scepticism from many corners of the internet. Some of these critiques are valid – from young comics, for example, complaining about a comedy dilettante getting coveted stage time at the snap of a finger – but most, sceptical about the idea that someone like Madonna could ever be funny, are less convincing. To be a fan of Madonna is to know that she is a genuine kook and, at the very least, someone who’s always been interested in using humour to puncture the sanctimonious, impenetrable vibe that most pop stars give off.

The press tour around Madonna’s turn in Evita and the album that followed, 1998’s Ray of Light, may have enshrined in the cultural memory the image of her as someone only willing to talk about spirituality and inner serenity, but really, that only lasted a few brief years. Madonna is rarely remembered as a great actor, but in films like Desperately Seeking Susan and A League of Their Own, Madonna is capable of seeming spunky, weird, and skin-crawlingly dry, often in the space of a single sentence, playing off co-stars Rosanna Arquette and Rosie O’Donnell, respectively, with the kind of over-the-top goofiness that only a true ham can muster.

Directly after Ray of Light, it seemed like Madonna was sick of being taken so seriously, and enlisted the most ridiculous of comedians to help her loosen up. Sacha Baron Cohen’s Ali G character was, amazingly, a key figure in the promotion of her 2000 album Music, appearing in the video for the title track and introducing her as Maradona on a European music show; a year earlier, she cut Beautiful Stranger, a song for Austin Powers: The Spy Who Shagged Me, and seduced Powers at the end of the track’s music video. In moments like these, the line between outlandish comedy character and over-the-top pop star became thinner than ever.

Later in her career, comedy became a way for Madonna to communicate more directly with her fans and the public. In 2012, after being dogged for years by comparisons to Lady Gaga, Madonna incorporated a mashup of her track Express Yourself and Gaga’s very similar song Born This Way into the set list of her MDNA Tour, adding in the hook of She’s Not Me for good measure. A few years later, she appeared onstage in a full clown costume for a show in Melbourne titled Tears of a Clown, in which bawdy jokes cut the tension between acoustic renditions of sad deep cuts and Elliott Smith covers.

This is not to say Madonna has never been totally humourless – see: when she likened an album leak to rape – nor is it to say that she is always in on the joke; her tweets and Instagram captions, no matter how serious the topic, always end up reading like parodies of dadaist poetry. None of the above moments suggest that Madonna would make a particularly good standup, either – for proof, just check out the time she tested material on The Tonight Show. But you can never tell me she’s not funny. Who else would spend much of her three-hour greatest hits show speaking to a mannequin dressed to look like her?