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Olivia Dean at MSG: The 5 Best Moments From the Second of Her Four Sold-Out Shows
The English singer-songwriter proves she's at the peak of her powers.
“This album has completely changed my life” may sound like a familiar sentiment that any artist might share during a new album cycle, but for Olivia Dean and her second LP The Art of Loving, it’s practically an understatement.
Midway through her Saturday (Aug. 15) night show in New York City, the English singer-songwriter paused to reflect on a transformative period that saw her go from opening for Sabrina Carpenter’s Short n’ Sweet Tour, which rolled into Madison Square Garden in fall 2025, to selling out four nights as the headliner at the same venue just 10 months later. “That was my first time in an arena,” Dean shared of opening for Sab. “This is crazy. Now we’re doing our own four shows here.”
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Olivia Dean Delivers Lessons in Love and One Hell of a Show at Madison Square Garden
There’s a word Olivia Dean consistently called to mind throughout her headlining performance at Madison Square Garden on Friday, Aug. 14 — present. The show was the first of four consecutive sold-out nights the British singer-songwriter has scheduled at the venue this weekend. She didn’t seem to be thinking too much about the other three, or really anything beyond that exact moment. Dean was astoundingly present.
It’s the most apt descriptor for the manner in which she commanded the room for nearly two full hours with a set spanning 24 songs. “I’m feeling emotional and grateful and so present with you this evening, New York,” Dean told the audience. It was early in the night and she just finished introducing the show with an opening run of “The Art of Loving,” “Nice to Each Other,” and “Lady Lady.” A brief encapsulation of how love lingers. A madly persuasive plea to live in the moment. A surrender to the inevitability of change. It was the exact order in which the songs appear on her acclaimed second album, The Art of Loving, which shares a title with the tour.
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