Vanessa Williams on Fame, Resilience and Regret: ‘I Shouldn’t Have Sent Her to Boarding School’

Vanessa Williams is a true multi-hyphenate: a recording artist with 13 Grammy nominations and over 212 million streams, an actor known for Ugly Betty and Desperate Housewives, and now the star of The Devil Wears Prada musical on London’s West End, playing the iconic Miranda Priestly.

But her journey to stardom wasn’t smooth. In 1983, she made history as the first African-American Miss America—only to be forced to resign when private photos, taken without her consent, were leaked to the press.

In this honest, funny, and no-holds-barred conversation, Vanessa opens up about overcoming public scandal, navigating fame, the truth about her romantic relationships, and—in a How To Fail first—why she regrets sending her daughter to boarding school.

00:00 Intro
02:47 Overcoming Scandal and Achieving Success
06:24 The Joys and Challenges of Stage Performance
10:31 Reflecting on Miss America
18:30 Family and Personal Reflections
23:40 Looking at Transparency and Shared Struggles
24:11 The Impact of Losing a Mother
26:00 A Mother's Influence on Trust and Relationships
28:51 Navigating High School Friendships and Trust Issues
30:07 Romantic Relationships and Parental Approval
34:58 Coping with Parental Loss and Family Dynamics
43:41 Musical Legacy and Family Bonds

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How to Fail is an Elizabeth Day and Sony Music Entertainment Production.

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