Friends and collaborators for decades, Loudon Wainwright III and Richard Thompson showed off their familiarity with each other – and with the Twin Cities – in a playful, barb-filled show Wednesday night at the Fitzgerald Theater. Talking about misprinted lyrics in his classic “I Want to See the Bright Lights Tonight” -- which he thinks may have permanently tainted his career -- Thompson surmised, “That’s why instead of flying over Minnesota, I stop, unlike many of my colleagues” Wainwright complained about losing Grammy noms twice in the ‘80s with Thompson-produced albums, both losses to his late friend Steve Goodman (“Oh sure, give it to the dead guy”). After finally winning one in February, Wainwright theorized, “Maybe Garrison Keillor will have me on his show now.” Their tag-teaming of “native son” Bob Dylan’s “You Ain’t Goin’ Nowhere” in the encore was certainly radio-worthy.

The old friends did a handful of songs together and full sets by themselves, starting with Wainwright. He opened with a pair of terrific new songs that referenced Bernie Madoff, cutting up credit cards and newspaper Real Estate sections ("horror shows"). He called them "songs about the New Depression... I'm hoping to cash in on this puppy, so hopefully it'll last long." The set also included the stirring "Another Song in C" (played on piano with many references to his late ex-wife Kate McGarrigle), "Florida," "Heaven," "White Winos," the Grammy-dreaming "Ramblings of a Ragged Clown" and "Daughter." Thompson came out near the end of Wainwright's set for "Fly Paper" and the (now-Grammy-winning) Charlie Poole song "If I Lose."

Thompson threw a few new ones into his set, too, and he ended with the riveting 2007 Iraq War battle song "Dad's Gonna Kill Me." But he also threw in plenty of old favorites, including "When The Spell Is Broken" and "Turning of the Tide" for the openers, "Vincent Black Lightning" mid-show and "Down Where the Drunkard's Roll" with Wainwright in the encore, which also included the Dylan song and the Lieber & Stoller standard "Smokey Joe's Cafe" -- a fittingly fun finale.