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Found this post looking for some stuff to add my list as I prep to return to gigging after a multi-year absence. I always found you could play some offbeat stuff if (1) you got a crowd engaged with stuff they knew; and (2) the offbeat stuff was funny or you sing or play it particularly well. Here's some stuff I do now:
You Can't Always Get/Walk on the Wild Side medley (this kills)
Wicked Game (chicks dig the yodeling)
Wilco -- California Stars, Passenger Side
Steve Earle -- Feel Alright, Hardcore Troubadore
Warren Zevon -- Lawyers Guns & Money, Mr. Bad Example (hilarious song nobody's heard but everybody loves)
Springsteen -- Thunder Road, Pink Cadillac
John Prine -- Please Don't Bury Me
Robert Earl Keen -- Merry Christmas From the Family
CCR -- Proud Mary, Bad Moon
Mountain Goats -- No Children (funniest dysfunctional marriage song ever)
Elvis Costello -- What's So Funny...
Johnny Rivers -- Secret Agent Man
James McMurtry -- Lights of Cheyenne
Van Morrison -- It Stoned Me
The Hold Steady -- Your Little Hoodrat Friend
Old 97's -- Question, Jagged, The Other Shoe, Barrier Reef
Lots of Buffett, Neil Young, more Springsteen, Morrison, Stones
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