Thursday, February 5, 2026

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‘It was totally crazy’: Harry Styles DM’d Madison Cunningham to ask her to support him on tour

Harry Styles DM’d Madison Cunningham to ask her to be his support act on tour.

The 24-year-old singer/songwriter admitted she was completely shocked when Harry dropped her a message to tell her he loved her debut album ‘Who Are You Now’ and asked her if she would support him at his Harryween Madison Square Garden gigs in October, which have now been postponed due to Covid-19.

Speaking to americansongwriter.com, Madison explained: "It was totally crazy! I was in the middle of a tour with Iron & Wine earlier this year and out of the blue I got a direct message from Harry himself. He was like, ‘I just wanted to reach out and say that I really love the record and I would love to connect at some point.’ I was, of course, blown away. I couldn’t have imagined that my record would have made it into his world.

"Then he said from there, ‘I don’t want to be forward but I would love it if you would somehow be involved in my touring this year.’ So that’s how it ended up coming about! None of us expected that. I’ve not met him yet, but from the way he’s communicated he’s just such a sweet guy and really [cares] about giving other people opportunities. That’s a rare quality in someone at his level and of his caliber, so that was so special."

Harry postponed his ‘Love On Top’ tour to next year, due to the global health crisis and Madison is still expected to join him for the rescheduled dates.

Harry previously said: "This summer we were excited to be bringing ‘Love on Tour’ to North America. However, due to the ongoing threat from Covid-19 we have been forced to reschedule these dates to next summer. The well-being of my crew and all the fans around the world will always hold top priority. I can’t wait to see you all out on the road as soon as it’s safe to do so."

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