How To Fail With Elizabeth Day

Episode: Jilly Cooper: On Failure, Love, and Literature

Release Date: October 6, 2025
Guest: Dame Jilly Cooper
Host: Elizabeth Day

Episode Overview

In this heartfelt and humorous episode, Elizabeth Day is joined by Dame Jilly Cooper—legendary author, journalist, and beloved chronicler of British society. The conversation explores Cooper’s life through the lens of her failures, from her struggles with hoarding and infertility to self-image and her comical attempts at driving. The themes of resilience, joy, and honesty run throughout, with Cooper generously sharing both wisdom and wit. The episode is especially poignant, as Day notes Cooper's recent passing, and it stands as a celebration of a remarkable life and literary legacy.

Key Discussion Points & Insights

1. Jilly’s Early Mischief and the Start of Her Career

• Jilly was dubbed "the Unholy Terror" at school for her naughtiness, a quality that latterly served her well as a writer and journalist.
• Her professional break came when she regaled the Sunday Times Magazine editor with stories at a dinner party, leading to an immensely popular column and interviews with public figures ([03:13]).
• Cooper’s transition to novelist led to international success, especially with the Rutshire Chronicles (notably Riders, Rivals, and Polo).

2. On Class and British Society

• Cooper is as adept at dissecting class as she is at writing sex scenes.
  • "We were so broke we were going to have to sell our house in Fulham. And then I wrote this book Class... was there for 20 weeks and saved our house." (Jilly Cooper, [06:49])
• On whether class is still relevant: "Probably not much, but I still think people look up and down at people... It just tilts, goes on secretly." (Jilly Cooper, [07:18])

3. Responding to Literary Snobbery

• Her books were often dismissed as "bonkbusters", but Day challenges this, highlighting the literary depth and social commentary in Cooper’s work.
  • "Do you actually think you don't write literature or have you been made to feel that you don't?" (Elizabeth Day, [06:04])
  • "I don't know what literature is... When things become literature, is it time?" (Jilly Cooper, [06:09])

4. The Real-Life Inspirations Behind Her Characters

• Discusses how her most famous hero, Rupert Campbell-Black, was an amalgamation of several "gorgeous men" she knew, including Andrew Parker Bowles ([08:13]).
• Cooper confesses to being "unnaturally obsessed with beauty" ([09:50]).

5. Family Dynamics, Grief, and Her Mother’s Struggles

• Jilly opens up about her mother's depression and a suicide attempt:
  • "She hated moving house... Every time she moved house she had a bit of a nervous breakdown." (Jilly Cooper, [12:27])
  • On discovering her mother's attempt: "He said, 'mummy, you know, she's had to go into a home. She tried to commit suicide.'" (Jilly Cooper, [12:38])
• Cooper’s desire to make people happy seems rooted here ("Yeah, I like making people happy. I mean, I'm a picture behind their backs. But I do like making love." [13:04])

6. Failures and Resilience

Failure 1: Inability to Throw Anything Away (Hoarding)

• "I always make about 15 drafts of everything I write, and I keep them..." (Jilly Cooper, [13:36])
  • Shared story of losing a manuscript for Rivals on a London bus, having to rewrite it from scratch ([19:01]).

Failure 2: Infertility and Adoption

• "I was married and we made love a lot... and nothing happened." (Jilly Cooper, [23:29])
• Candidly discusses the pain, stigma, and personal acceptance around infertility, and the ultimate joy adoption brought her:
  • "I could never love any much as I love them. So I was incredibly lucky..." (Jilly Cooper, [24:22])
• Encourages listeners facing similar challenges to consider adoption: "I'd say go absolutely for it's been wonderful. It made me so happy..." (Jilly Cooper, [25:24])

Failure 3: Diets and Self-Image

• Though a celebrated beauty, Cooper shares lifelong body insecurities.
• "[When] I get a little bit thinner, I get smug." (Jilly Cooper, [27:56])
• The roots stem from hurtful comments in youth: "She just said I was ugly and fat. And that's clearly stuck with you. It did. It did." ([29:44])

Extra Failures

• Cooper also admits to failures with technology ("Oh, God. Awful...I don't use a laptop...I can't do any of that." [32:52]) and delayed driving proficiency ("Passed my [driving] test for the second time. Everybody fainted at home..." [35:37]).

7. On Friendship and Fame

• Friendship is central, but as a writer, she resists "droppers in" when in her creative flow ([36:38]).
• Reflects on fame: "In the old days everybody recognized. Now they don't anymore." (Jilly Cooper, [37:29])
• Discusses the changing nature of fandom and correspondence in the digital age: "The internet's different, don't you think?... they don't say who they are..." ([38:17]).

8. Reflections on Aging, Success, and Self-Acceptance

• Cooper, in her 80s, exudes gratitude for her family and life, expressing only some longing for her late husband, Leo:
  • "I'm very happy, but I mean, I miss Leo, but it's fine. I live in a lovely house and... my children very near..." ([30:39])
• On being honored with her damehood, she says:
  • "When I got the letter about being a dame, I mean, it arrived at home and I opened it and I thought, oh, somebody's fooling around." ([38:48])

Notable Quotes & Memorable Moments

• "I'm sort of frivolous... I don't write literature, but I hope my books have given people joy." – Jilly Cooper ([04:46])
• "I love beautiful people. I'm unnaturally obsessed with beauty, I think." – Jilly Cooper ([09:50])
• "The good marriage was kept alive by creaking bedsprings, more from laughter than from sex." – Jilly Cooper ([13:15])
• "I had this fantasy about some bus conductor writing the novel of the century." – Jilly Cooper, on losing her manuscript ([19:08])
• "You dust yourself off and carry on. Would that be fair?" – Elizabeth Day ([20:39])
• "I'd say go absolutely for it... It made me so happy." – Jilly Cooper, on adoption ([25:24])
• "I'm hopeless [at technology]... but Shakespeare did all right, didn't he, without these things?" – Jilly Cooper ([32:52])
• "I think I was mean." – Jilly Cooper, on early correspondence and the nature of modern social media ([38:38])
• "I want to cheer people up, that's what I like to do." – Jilly Cooper ([39:28])

Important Segment Timestamps

| Timestamp | Segment | Description | |-----------|----------------------------------------|----------------------------------------------------| | 03:13 | Opening biography and intro | Day summarizes Cooper's career trajectory | | 06:04 | Literature vs. popular fiction | Their exchange about literary merit and labels | | 06:49 | Reflections on class | Cooper recounts writing "Class" and saving her home | | 08:13 | Inspirations for iconic characters | Cooper discusses men who inspired Rupert Campbell-Black| | 12:27 | Mother's struggles and resilience | Talking about her mother's depression and recovery | | 13:36 | Hoarding and drafting process | Jilly discusses her writing habits | | 19:01 | Losing her “Rivals” manuscript | The infamous London bus story | | 23:29 | Infertility and adoption story | Candid story about discovering infertility | | 25:24 | Advice to those considering adoption | Warm encouragement to listeners | | 27:29 | On diets and self-image | Cooper’s lifelong struggle with body image | | 32:52 | Failing at technology | Tales of typing, typewriters, and aversion to tech | | 35:37 | Driving test misadventures | Late-in-life driving lessons | | 37:29 | Shifting nature of fame and public | Cooper reflects on public recognition | | 39:28 | Essence of her legacy | Her mission to bring joy and champion kindness |

Tone & Atmosphere

The conversation is intimate, full of warmth, humor, and self-deprecation, with Jilly Cooper’s infectious laugh lightening even the more difficult subjects. Elizabeth Day’s admiration is palpable, and together they create a candid, uplifting examination of legacy, resilience, and the unlikely gifts of failure.

Summary Takeaways

• Legacy through joy: Despite critical dismissals, Cooper’s books have made a generational impact, offering both escapism and shrewd social truths.
• Resilience: Whether in the face of professional, personal, or bodily failure, Cooper models acceptance, humor, and persistence.
• Honesty about insecurity: Her admissions of self-doubt and lifelong feelings of inadequacy resonate powerfully, especially for women.
• Power of reinvention: From hoarder to bestselling author, and from failed fertility to joyful adoption, Cooper reclaims her story at every turn.

Closing

This episode stands as a tribute to Jilly Cooper’s irrepressible spirit and her ethos of delighting and comforting readers, even—especially—in the face of failure.