Vanessa Williams - ‘It would be hard to be married to me!’

Vanessa Williams - ‘It would be hard to be married to me!’

Author: Elizabeth Day and Sony Music Entertainment July 16, 2025 Duration: 50:33
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

There's a quiet revolution happening in how we think about success, and How To Fail With Elizabeth Day is right at the heart of it. This isn't about schadenfreude or wallowing in misfortune. Instead, Elizabeth Day has created a space where the most interesting conversations begin with a simple, radical premise: our lowest moments are often our greatest teachers. Each episode, a guest-from celebrated artists and thinkers to everyday people with extraordinary stories-sits down to examine three significant failures from their own life. The magic lies in the excavation, as Elizabeth guides the discussion toward the unexpected wisdom and resilience that emerged from those setbacks. You'll hear the raw honesty in their voices, the laughter that comes with hindsight, and the profound clarity that failure can uniquely provide. This podcast, presented by Elizabeth Day and Sony Music Entertainment, digs into the messy, human stuff of life that connects us all, transforming shared vulnerability into a source of collective strength. It’s a reminder that the path to any meaningful achievement is rarely a straight line, but a series of instructive detours. The show actively invites listeners to reflect on their own stories, fostering a genuine community around the idea that we can all succeed better by understanding where we've previously stumbled. Tune in for conversations that are as comforting as they are challenging, and which might just change your perspective on what it means to live a well-lived life.
Author: Language: English Episodes: 100

How To Fail With Elizabeth Day
Podcast Episodes
ON MOTHERHOOD… with Jessie Ware and Francesca Segal [not-audio_url] [/not-audio_url]

Duration: 19:11
Motherhood is often portrayed purely as a joyful, magical chapter of life – and while it certainly can be – we rarely speak openly about the hard, exhausting and deeply challenging truths. In this episode, singer‑songwri…
Toni Laites - Love Island Healed My Toxic Dating Patterns [not-audio_url] [/not-audio_url]

Duration: 54:51
Toni Laites made history last year as the first American to win Love Island, but her journey to the villa was anything but ordinary. Discovered in Las Vegas working as a cabana girl by the show’s creative director, Toni…
ON AMBITION… With Gillian Anderson and Munroe Bergdorf [not-audio_url] [/not-audio_url]

Duration: 12:20
Ambition can be a powerful force: it propels us forward, sharpens our focus and pushes us to dream bigger. But it can also whisper that we are only as good as our latest achievement - and these two brilliant former How t…
Baz Luhrmann - ‘I self-medicate with creativity’ [not-audio_url] [/not-audio_url]

Duration: 50:25
Few filmmakers have a style as bold, romantic and unmistakable as Baz Luhrmann. From his breakout debut Strictly Ballroom to the glittering spectacle of The Great Gatsby starring Leonardo DiCaprio, and the fever-dream en…
ON SELF ACCEPTANCE... With Pamela Anderson and Rylan Clark [not-audio_url] [/not-audio_url]

Duration: 23:31
Welcome back to this How to Fail special where we revisit conversations from the archive to highlight particular themes and tap into the wisdom they contain. This week we look at two guests who have learned self acceptan…
Jennette McCurdy on Reclaiming Her Voice [not-audio_url] [/not-audio_url]

Duration: 57:06
This episode includes discussion of eating disorders, including anorexia and bulimia. Listener discretion advised. This might be one of the most powerful conversations I’ve ever had on How To Fail. I don’t say that light…
ON FAMILY DYNAMICS… With Bella Freud and Danny Dyer [not-audio_url] [/not-audio_url]

Duration: 21:48
Families are fascinating: how those first bonds shape our understanding of love, security and ourselves. In this episode, we revisit episodes with Bella Freud and Danny Dyer, who each open up about the simultaneous beaut…
Mo Gilligan - Fatherhood Is A Gift I Didn’t Know I Needed [not-audio_url] [/not-audio_url]

Duration: 52:12
Mo Gilligan started out working in retail (think Jo Malone and Levi’s) but quit in 2018 when his online comedy videos went viral. The leap paid off - sell-out tours across the UK, a late-night entertainment show on Chann…