In this episode, Scott sits down with legendary host and comedic trailblazer Craig Kilborn for a wide-ranging conversation on life after late night, creative independence, and what it really means to stay above the fray. From his iconic runs at ESPN, The Daily Show, and The Late Late Show, Craig reflects on the highs of fame, why he walked away, and how he found peace (and punchlines) off-camera.

Scott and Craig share their philosophies on aging gracefully, drinking in moderation, and never chasing the night. They riff on Frasier, Scotch, the Reuben sandwich, and their favorite rewatchable movies—from Predator to North by Northwest. Plus, Craig shares what he’s up to now with his podcast The Life Gorgeous, his love for California road trips, and why leadership and attitude matter more than ever.

Lessons Learned:

- Why Craig Kilborn left late night at the top—and doesn’t regret it.

- How to craft a creative life without burnout or bitterness.

- Why being genuinely happy is a competitive advantage.

- What makes a sandwich truly great.

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Subscribe to Craig’s podcast: The Life Gorgeous

Follow Craig on Instagram: @mrcraigkilborn

Follow Scott: @kitun