As a recording artist, Vanessa Williams has earned 13 Grammy nominations and racked up over 212 million digital streams over the course of her eight albums. Her most popular hit, Save The Best For Last, was Number 1 for five weeks in 1992.

She is also a highly successful stage and screen actor, appearing in Desperate Housewives and Ugly Betty. She is currently starring on the West End stage as Miranda Priestly in the musical adaptation of The Devil Wears Prada.

It’s all a long way from her historic crowning as the first African-American Miss America in 1983 - she was later forced to resign after unauthorised photos taken when she was a student were leaked without her consent.

Vanessa joins us for an honest, hilarious and no-holds-barred conversation about her childhood, her romantic relationships, and - in a How To Fail first - why she regrets sending her daughter to boarding school.

Elizabeth and Vanessa answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content

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

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com

I have an upcoming one-off show at Cadogan Hall on 21 Sep for my new novel One of Us. Full show details here: ⁠https://www.fane.co.uk/elizabeth-day

Production & Post Production Coordinator: Eric Ryan

Studio & Sound Engineer: Matias Torres

Assistant Producer: Suhaar Ali

Senior Producer: Hannah Talbot

Executive Producer: Carly Maile

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

Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts

To bring your brand to life in this podcast, email podcastadsales@sonymusic.com

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is the Church Where Creativity Goes to Die?