You Made It Weird with Pete Holmes Jimmy Kimmel (Re-Release)
Oct 10, 2025
In this lively conversation, late-night host Jimmy Kimmel shares insights from his comedic journey. He discusses the pressures of masculinity, reflecting on how parenting shapes a man’s perspective. Kimmel reveals his struggles in early radio jobs and why hardships enrich comedy. They dive into the ethics of pranking and the art of interviewing celebrities, highlighting the balance between authenticity and production. Lastly, they explore the meaning of life, fame's impact on relationships, and the quirky habits that come with celebrity status.
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Coming-Of-Age Moving Test
- Jimmy Kimmel describes marrying at 20 and moving cross-country as a formative, terrifying adulthood test.
- He credits packing and driving a 26-foot truck from Seattle to Phoenix with giving him a real sense of accomplishment.
Failed Relationships Teach You
- Kimmel says relationships that end aren't failures; they teach you and improve future partnerships.
- He reframes past romances as growth experiences, not wasted time.
Avoid Living By The Calendar
- Avoid over-scheduling and the dread of fixed obligations when possible.
- If you must, agree far in advance and let future-you handle the burden, but it's a poor way to live.