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Aug. 4, 2026

Brandy's Biggest Hits: The Playlist That Reminds You Why She Was Everything

Brandy's Biggest Hits: The Playlist That Reminds You Why She Was Everything

It's hard to imagine that Brandy is in her late 40s. Yes, I know, we don't necessarily need to talk about someone's age. But 50 For 50 is about aging and growing and doing so with grace and wisdom. As Mike Joseph and I talk about some of our favorite artists and albums, one of the things that stands out is how hard celebrity and especially the music industry can be.

In 1998, Brandy was sitting on top of the world. She and Ma$e. But in 2026, she's more known for the memories of what she's done than anything she's currently doing. Which is why, her memoir came out at the perfect time. 

It was both a great reflection about who we remembered her as, as well as a look at how she got there and the steps she's currently taking to live a fulfilling life. 

On our Brandy playlist, Big Money gives you all the big hits and other songs that you may not be super duper aware of. You can listen on Spotify or Apple Music below.

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What are the greatest Brandy songs ever recorded? Mike Joseph and Garrett Gonzales rank their Top 5 favorites and defend every pick. Before the list, they play Rock With It/Stop With It on two of Brandy's most iconic tracks — "The Boy Is Mine" and "Baby" — forcing some tough choices. Then it's straight into the countdown, featuring "Brokenhearted," "Top of the World," "Sittin' Up in My Room," "Long Distance," and more. If you love Brandy, R&B, or just two people who take their music opinions ver...