Da Brat & Judy: Love and Happiness Are Not the Same | Outlaws with TS Madison

“Outlaws” is starting 2026 out strong, with TS Madison’s dear friends, superstar power couple Da Brat-tat-tat and Kaleidoscope Hair Products CEO Jesseca “Judy” Dupart!

In the spirit of Capricorn season, we get marketing 101 from Judy and what she taught TS Madison about personal branding. It was a brand deal that brought this couple together– the pair tell us how a rapper and a beauty mogul fell in love out of the public eye, from a business meeting turned date to a “Coming to America” style proposal to launching a reality TV series together.

Next, Da Brat gets into her decision to keep her sexuality private during her early fame, why she felt it was an act of protection rather than hiding, and how Judy inspired her to come out publicly. And we’re rewinding even further back, as Judy breaks down her 2007 arrest and what she learned in prison.

Also: Unlearning stereotypes; why Da Brat doesn’t consider herself a Stud; fire sign/air sign romance; how “Brat Loves Judy” came to be; and navigating pregnancy on TV.

Plus a sneak peak and Da Brat and Judy’s upcoming memoir, “The Way Love Goes: A Guide to Building a ‘Beaurtiful’ and Everlasting Relationship”, out next month! Pre-order now!

"Outlaws" is hosted by TS Madison, and is part of the Outspoken Network from iHeartPodcasts, co-produced by Turtle Run Entertainment.

Is it on? Is it on?? Honey, is this thing recording?! TS Madison broke the Internet with six seconds and a 22-inch weave. And she didn’t just go viral — she became part of the culture, from “RuPaul's Drag Race” to Beyoncé’s “Renaissance.” Her superpower? Her voice. Her kryptonite? Doesn’t exist. Her podcast? The one they never saw coming.

Each week on “Outlaws,” Madison sits down with living legends and rising stars who shed their armor and own their stories — turning side-eyes into sermons, pain into punchlines, and grief into galaxies. They speak when silence is safer. They dream when told to disappear. And they know what so many are taught to fear: that when you speak your truth, you open a portal.

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