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Debbie Harry's awkward chance meeting with Donald Trump


There are some people it’s just impossible to imagine being in the same room. Joan of Arc and Colonel Sanders, or Jimi Hendrix and Dappy from N-Dubz. These people are just incompatible, warring magnets that no amount of strength can bring together. I would have used Blondie and former US President Donald Trump as an example, but it turns out the pair did meet before he decided to run for office in 2016.

So, how did such a bizarre meeting come to be? As the vocalist of Blondie, Debbie Harry is the very embodiment of female punk empowerment. With her anarchical performance style, wry lyrics and no-fucks-given attitude, she helped redefine the role of women in music, all while helping to craft some of the most accessible and danceable music of New York’s downtown punk scene. She’s hardly the kind of person to wander into Trump’s office and apply for a job as an intern, even if she did work as a PA for the BBC before Blondie found success.

Harry’s introduction to the American businessman came through her partner at the time, Penn Jillette, one half of the magical duo Penn and Teller. Harry and Jilette started dating in 1995 after her separation from Blondie bandmate Chris Stein in 1989. The relationship didn’t last long, with the pair going their separate ways in 1996, but they remained on good terms. So much so that when Penn was invited onto the celebrity version of the reality TV show The Apprentice, he asked Debbie Harry to come along. During her time on set, she bumped into a man who would go on to divide US voters.

Speaking to The Big Issue in a recent interview, Harry said: “I used to see Penn Jillette from Penn and Teller and we’ve remained friends. He was on [The US version of The Apprentice doing a task where they had to invent a new flavour of ice cream and invite people along to try it. He invited me along and introduced me to Trump, who just said ‘hello’ and walked right off. It was so brief, I was surprised. I guess maybe I wasn’t tall enough for him.”

It’s hard to say what Trump made of Harry, but it’s clear that Jilette found his experience on The Celebrity Apprentice to be an uncomfortable one. Opening up about the experience on Big Think, he confessed that being surrounded by cameras and competitors for 12 hours a day drained his willpower, leaving him totally “unconfrontational”.

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