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To understand why O’Brien chose this particular song, you have to look back to the transition era of late-night television. On February 20, 2009, O’Brien wrapped his 16-year run at Studio 6A in Rockefeller Center. Rather than booking an over-the-top stadium act, Conan invited Jack and Meg White to close the broadcast. The Detroit duo had stepped away from live touring in late 2007 due to Meg’s acute anxiety, making their appearance entirely unexpected.

Sitting side by side on a pair of wooden chairs, Jack played acoustic guitar while Meg sat beside him, tapping a single snare drum. Conan himself joined them for the final chords, visibly moved on national television. It would turn out to be the final concert and live appearance The White Stripes ever delivered before officially disbanding in 2011.

The performance crystallized Jack White's commitment to Conan’s creative orbit. When Jack founded Third Man Records in Nashville, O’Brien was among the first outside performers invited to record a live-to-acetate rockabilly album inside the facility’s Blue Room. Replaying that track at a massive comedy festival was not a lark; it was a public nod to a piece of rock history that O'Brien has carried as a personal badge of honor for fifteen years.