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Macy Gray brings 25th Anniversary Tour to Hard Rock Live Orlando performing On How Life Is October 22

Alastair Mac
30 minutes ago
3 min read

The Grammy-winning singer Mach Gray adds Orlando tour stop to ‘On How Life Is 25th Anniversary Tour.’

Macy Gray brings her 25th Anniversary Tour to Hard Rock Live Orlando performing On How Life Is on October 22

Macy Gray is adding an Orlando show to her recently concluded On How Life Is 25th Anniversary Tour. The Grammy-winning singer has unveiled she will take to the stage at House of Blues Orlando on Wednesday, October 22, 2025!

The North American Tour kicked off back on July 10 at House of Blues in Anaheim, California., with the tour seeing Gray performing the U.S. and Canada, making stops in Portland, Vancouver, Denver, Chicago, Houston and more, before concluding on August 16 in Los Angeles.

Gray’s tour celebrates the milestone anniversary of her debut album, On How Life Is. The album was released July 27, 1999, via Clean Slate/Epic Records. The Orlando show will see Gray perform the album in full, before diving into some of her other hits and fan favorites.

Tickets for the Orlando show on October 22, 2025 are on sale now!

https://www.ticketmaster.com/event/2200631BAA18144C

Check out the latest concerts and music news in Orlando and Tampa! From major headlining tours, to local indie music nights, Orlando features an eclectic music scene! Catch the latest shows at Kia Center, House of Blues, The Plaza Live, Hard Rock Live, Addition Financial Arena, The Social, The Vanguard, Conduit, Will's Pub, and more.

Macy Gray is a multi-award-winning American musician, songwriter, producer and actress. She has drawn comparisons to some of the world's most celebrated; including Billie Holliday and Janis Joplin. She is most renowned for her own approach to sound, lyrics and fashion.

Macy's first live performance was at a downtown Los Angeles hotel singing jazz standards for Sunday brunch. "I'm singing my heart out, and everybody's at the buffet or the bar, talking way louder than I could sing. No one was paying attention to me, but that was ok because I didn't have much confidence in my voice at the time." After graduation, Macy opened her own night spot in Hollywood, called: THE WE OURS, a small cafe that featured open mic on the weekends.

Over the next few years, Macy would work several jobs, most notably as a production assistant at MTV and VH1. In her spare time, she was recording whenever she could, making "demo tapes," mailing them to record labels, playing clubs on the Sunset Strip. In 1994, Atlantic Records A&R, Tom Carolan, happened to catch her performing at the Roxy. He signed the 25 year old, and Macy recorded her first album: "Thing of Beauty."

That same year, Macy found out she was expecting. Upon Atlantic hearing the news, Macy was dropped from the label and "Thing of Beauty" was never released.

By 1997, Macy was married with three kids, living in North Hollywaood. With so much new responsibility, her dreams of stardom seemed far away. When she separated from her husband and moved back to Ohio to live with her mom, she had no idea that her demo had landed on the ears of Jeff Blue, an executive at Zomba publishing.

Miraculously, Jeff got a hold of Macy's Ohio phone number and called. He expressed that he was particularly excited about a song on the tape called: "I Try." Jeff shopped the tape to label execs and in the winter of '98, Macy was invited to meet the President of Epic Records, the late Ms. Polly Anthony.

The label released "Macy Gray on How Life is" on July 1, 1999. It is 5 time grammy nominated and sold over 9 million copies.

Before attending any of the events listed on Gotta Go Orlando, you should contact the organizer or venue to confirm that the event is taking place as information, changes, and cancellations can occur.

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