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A Tribute and an Apology to Vic Chesnutt

Sep 23, 2026 · 11m

Summary

In this bonus episode, Greg Kot and Jim DeRogatis discuss the late singer-songwriter Vic Chesnutt, highlighting his unique artistry and tragic life. DeRogatis shares an embarrassing anecdote about a heated 1998 SXSW panel where he criticized Paul McCartney, causing Chesnutt to become upset. The hosts reflect on Chesnutt’s final album, *Flirted With You All My Life*, and his death in 2009, ultimately expressing deep respect for his legacy and apologizing for the earlier friction.

Topics discussed

Desert Island Jukebox intro Welcome and Patreon support Teaser for Vic Chesnutt segment Goose Island Beer sponsorship Listener story: Rob LaHood at block party Return to show and Patreon plug Introduction to Vic Chesnutt and Mark Kemp Vic Chesnutt's biography and early career Sweet Relief benefit and mainstream recognition Jim's embarrassing SXSW panel story Details of the Paul McCartney debate Vic's reaction and Jim's regret Analysis of 'Flirted With You All My Life' Vic Chesnutt's death and apology Audio clip: Flirted With You All My Life Reflections on Vic's character and legacy Debate on McCartney's legacy and consistency Discussion on Flaming Pie and batting averages Closing credits and sponsor info The Zone boxing event promotion
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