PHOTOS & REVIEW | Jesse McCartney Shines at Massey Hall in Toronto, 2025

This past Thursday night, October 16, 2025, Massey Hall transported fans back to the early 2000s. Jesse McCartney took over the downtown Toronto stage with opener Ana Sky as part of The Weightless Tour.

Ana Sky opened the night, stepping onto the stage in a stunning white pearl veil that shimmered under the lights. Her smooth vocals and calm confidence immediately drew the crowd in. Once working in STEM, Ana is now living a dream she never imagined. She ended her set with a sneak peek of new music to come.

As Jesse’s band launched into the intro, the room buzzed with anticipation. When he finally appeared, Jesse took the stage with charisma and warmth that immediately captivated the audience. It was clear he hadn’t lost a step, his vocals were strong, his energy infectious, and his connection with the crowd undeniable.

Between hits, Jesse shared stories about becoming a new dad, giving fans a glimpse of his life offstage. He showcased his dance moves, smooth and precise yet full of playful humour that had the crowd smiling. In true McCartney fashion, he had everyone laughing when he brought out his iconic Judge Judy impression, a TikTok favourite that had the audience roaring. The night was filled with timeless songs we once had on shuffle on our iPods, alongside new tracks that had everyone dancing.

To close the night, he delivered the song everyone had been waiting for, “Beautiful Soul.” The entire hall sang along, a perfect ending to a night that showed Jesse’s magic hadn’t faded one bit.

PHOTO GALLERY: Jesse McCartney at Massey Hall in Toronto, 2025

GALLERY: Ana Sky at Massey Hall in Toronto, 2025

Words & Photos by Lacey Davey