What do The Beatles, Linda Ronstadt, Billy Joel, Bonnie Raitt, James Taylor, Robin Williams, Pamela Anderson, Courtney Love, and Cher have in common? Veteran record producer and manager Peter Asher has worked with all of them, and he chats with Billy about the highs, the lows, and the just plain surreal.

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From a young age, Chely Wright knew two things to be true: she was destined to be a country music star, and she was gay. But for many, many years she thought she could only publicly be one of those, and it nearly killed her. Her candid conversation with Billy is about the connections between f*cking up, acceptance, and survival. If you or someone you know needs help, it’s available 24/7:

LGBTQ+ Crisis/Suicide Prevention Hotlines:Transgender CommunityTrans Lifeline - 877-565-8860LGBTQ+ YouthLGBT National Youth Talkline - 1-800-246-7743TrevorLifeline - 1-866-488-7386TrevorText - Text START to 678-678The Steve Fund Crisis Textline* - Text STEVE to 741741LGBTQ+ AdultsLifeline* - 1-800-273-8255Crisis Text Line* - Text HOME to 741741All AgesLGBT National Hotline - 1-888-843-4564
*Not LGBTQ+ specific but LGBTQ+ inclusive

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Country rocker Tim Montana grew up off the grid, living in poverty, and found playing guitar as a passion and escape from a rough home life. Billy explores the failures and successes on Tim’s journey from founder of an elementary school “Cuss Club” to hitting it big, befriending Charlie Sheen who directed his first music video for Tim, and becoming a devoted family man. 

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Jill Kargman has no filter. Censors be damned, she will say anything on her mind. It’s been her biggest asset AND caused her most colossal f*ck-ups. How can a personality trait be your golden ticket, and your biggest failure, simultaneously?

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Whether you associate Michael Bolton with love songs, luscious locks, or Captain Jack Sparrow, you probably think you know him pretty well. But the man behind one of the most distinctive voices ever gets raw and emotional with Billy as he explores f*ck-ups at various stages of his life and mega-career.

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In 1991, Evan Handler made headlines for walking off the stage in the middle of a Broadway production of “I Hate Hamlet.” More than 30 years later, he has firmly solidified his spot as a fan-favorite sex-icon on the Sex and the City revival And Just Like That... With Billy’s help, he’s still
processing the public and private moments of regret and humiliation that happened in the decades in between.

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Aly & AJ started out as a teen pop-duo and then took a decade off from music - what happened? Billy speaks to the musical sisters about their professional break from music, and what the effect child stardom had on their parents' relationship. From dealing with mental health issues to witnessing a mass shooting, getting back on tour hasn’t been a walk in the park. These young talented artists are bravely open about the struggles they’ve faced together and
individually

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As talented and driven as Liz Gillies is there may be one thing standing in her way... herself. The actress, who started out professionally at the age of ten, goes on a journey with Billy to highlight a number of fuck-ups and life lessons she’s learned over the years. In looking back at her blunders, she realizes that holding herself back is perhaps responsible for what she considers her biggest life fuck-up to date.

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How does one of the most legendary music executives miss out on one of the biggest pop icons of all time? It’s a story only L.A. Reid can tell. He also dishes on the fateful night that changed his career—and life—forever.

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“If there was ever the perfect example of a yeah-I-f*cked-up profession, it’s standup,” says comedian and writer Hari Kondabolu. And while that approach got him through faceplant moments on some of the biggest stages, nothing quite prepared him for the life-changing experience he had aboard a train from Seattle to Portland.

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