Are Macy Gray and Britney Spears Friends? Macy Opened Up About Their Memorable Interaction

Once upon a time, many of us would sing and dance to songs by Britney Spears with aspirations of being like her one day. But we’re not the only ones. R&B singer Macy Gray has spoken before about her love for Britney as a performer, but not until 2024 has she revealed the true nature of their relationship, whether they are friends or foes.

Macy appeared on the Australian talk show The Project, on which she revealed whether or not she and Britney were friends. As she told a funny story about Britney from the past, viewers and listeners couldn’t help but wonder if the two are friends today. So are Macy Gray and Britney Spears friends?

While Britney Spears may be a household name for various reasons, Macy is a relatively under-the-radar superstar. In the early 2020s, Britney became front-page news once again as fans advocated for her freedom from her conservatorship in the #FreeBritney movement. Meanwhile, Macy has continued to tour and build up her decades-long career.

As a contemporary to Britney, Macy won a 2001 Grammy for her single “I Try” in the category of Best Female Pop Vocal Performance, beating out Britney’s “Oops!... I Did It Again.” With the timeline of their rise to fame, it seems plausible that Britney and Macy could be friends. However, Macy told viewers about her most memorable interaction with Britney many years ago when they were in the recording studio.

Macy told The Project presenters, "We were in the same studio once, and she skateboarded into my session. Literally. She was in the room down the hall, and we looked up and all of a sudden she was skating into our room. And then we talked for a little bit and we didn't really, like, hit it off."

Luckily, that didn’t mar her image of Britney. "I'm still a groupie to this day. I'm sitting there with Britney Spears, you know, and I kinda stuttered," she said. "I didn't know what to say. And she kinda rolled her eyes. Whatever I said, she was kind of annoyed by it and she left. She rolled her eyes and she rolled out!"

Even still, Macy added that Britney’s album Blackout was “the best album ever” and that the song “Radar” is still one of her all-time favorites. She shared that Blackout gave her the “let’s go!” energy she needed before performing, so despite her awkward encounter with Britney, Macy was still inspired by her music.

Macy didn’t add anything else about their relationship, which leads us to think that that’s the extent of it. If they did become greater friends, Macy didn’t allude to that in any way. So perhaps they’re just musical contemporaries. Of course, Macy has always seemed to harbor a great respect for Britney and what she does.

In 2007, Brandon Voss asked Macy if she had any advice for Britney, who was in the news because of her decision to shave her head. “Her life is very different from most people's. She's going through a lot, she just had another baby and went through a divorce, everybody's watching her, and I think that would be very difficult for anybody,” Macy said respectfully, not feeding any fuel to the fire.

“She's human and those are very heavy situations for anyone to deal with, and I'm sure it just doubles it that everyone watches and makes fun of it. So I actually feel really bad for her,” she said at the time. Later in the interview, Macy added her own sentiment about publicly perceived “craziness.” She said, “Craziness is such a subjective word. You can be crazy any time you stand out or do things differently.” Both Britney and Macy have done that, so maybe they’ll be friends in the future.