Bob Dylan has spent the past few weeks spotlighting local artists and city-specific songs while cross-crossing America on his Rough and Rowdy Ways tour. It began October 1 in Kansas City when he opened up with “Kansas City,” continued in St. Louis where he covered two Chuck Berry songs, and carried on in Chicago where he broke out Chicago blues tunes by Muddy Waters and Howlin’ Wolf.

Perhaps the biggest curveball came October 16 in Indianapolis, Indiana when he played John Mellencamp‘s “Longest Days.” It’s a relatively obscure song from Mellencamp’s 2008 LP Life, Death, Love, and Freedom. Dylan quoted it in his 2015 MusiCares Person of the Year acceptance speech. “It’s one of the better songs of the last few years, actually,” Dylan said. “I ain’t lying.” Here’s audio of Dylan’s cover:

Dylan and Mellencamp have been buddies for years, and they toured together in 2009 and 2010. “Bob Dylan used to call me up in the middle of the night and read his lyrics to me that he was working on for new records,” Mellencamp told Billboard in 2022. “And I finally told him, ‘Bob, would you quit calling me, because I’m not gonna say anything. I’m not a good sounding board because I like everything you do. I’m happy to hear this stuff, but I’m not that great of a sounding board.’”

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When Dylan’s tour hit Cincinnati, Dylan surprised the crowd with Dwight Yoakam‘s “South of Cincinnati.” The song appears on Yoakam’s 1984 debut EP Guitars, Cadillacs, Etc., Etc. It’s sad ballad about an ex-couple that long for each other. “If you ever get south of the Ohio River down where Dixieland begins,” Yoakam wrote. “If you ever get south of Cincinnati I’ll be yours again.”

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Dylan touched down in Akron, Ohio after Cincinnati, giving him plenty of chances to honor local artists like the Pretenders, Devo, or the Black Keys. But he decided to instead revive “South of Cincinnati,” even though he was decidedly north of Cincinnati by that point. In the coming days, the tour heads to Erie, Pennsylvania and Rochester, New York before moving into Canada. It’s impossible to know what surprise songs might pop up at those shows. But when the tour hits Brooklyn in mid-November, we’re hoping to hear some Notorious B.I.G. That obviously sounds impossible, but was anyone predicting a 2008 John Mellencamp deep cut prior to this week?

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