Rupert Everett on Hollywood Rejection, Ego and Growing Older

Rupert Everett is the best type of A-list guest. He’s been through the highs and the lows of fame and come out of the other side wiser, stronger, and with no qualms about speaking his mind. Plus his new book ‘The American No’ was born from failure (a collection of brilliant short stories that were TV and film ideas). We talked about: ‘learning to die’ professionally; his love for fragile but strong women such as Paula Yates (with whom he had a 6-year affair); coming out in Hollywood; Madonna; My Best Friend’s Wedding with Julia Roberts and Cameron Diaz; why Oscar Wilde is a Christ figure, how drugs have ruined his brain and using hyper-sexuality as an escape. See, told you he didn’t hold back. 00:00 Intro 02:18 Success and Fame Mechanics 05:56 Boarding School Emotions 07:37 Failure as Motivation 10:09 Gay in Soviet Russia 12:29 Thoughts on Death 18:56 Sexual Liberty and Career 22:49 Jealousy and Oscar Wilde 26:15 Letting Go of Guilt 26:42 Drugs and Staying Lucid 28:11 Friendships and Fragile Icons 33:32 Remembering Paula Yates 36:40 Best Friends Wedding 44:15 Failure to Rebirth 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 [email protected] 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Have something to share of your own? I'd love to hear from you! Click here to get in touch: howtofailpod.com All guest booking for How To Fail comes from an official @sonymusic email address.