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When your stock-in-trade is arch white-boy funk—the kind that boosted a thousand launch parties in the dot-com ’90s—the second act of your career is bound to be a little clumsy and full of odd moves. Hey, you started out odd. So when Mike Doughty, former Soul Coughing frontman and Suicide Girls photog, played the 9:30 Club on Saturday night, he closed up the main set with a cover of Kenny Rogers’ “The Gambler,” a tune he included on a 2005 EP. Why might he do such a thing?

1. Mike Doughty Was Being Amusingly Ironic The first single from his new album, Golden Delicious, is called “27 Jennifers,” and his MySpace page has 27 Jennifers, Jennys, etc, in his top friends list. And toward the end of 9:30 Club set, he warned the crowd that he and his band would dispense with the usual encore rigmarole and instead just stand with their backs turned for a few seconds. So, playing a ditty about a guy who gets conned out of whiskey and cigarettes in exchange for some useless poker advice before cranking out the fan favorites? Total irony move.

2. Mike Doughty Is Not Being Ironic at All and Instead Admires the Impressive Structural Integrity of “The Gambler,” Which, to the Best of My Knowledge, Is the Only Pop Song to Inspire a Made for TV Movie “It really, REALLY wasn’t intended to be ironic,” Doughty told Austinist last October. “It’s a great song! I think a lot of things that are considered hipster-irony-statements are in fact sincere—the artifacts that get re-framed as “irony” are usually really beautiful things.”

3. Doughty Sincerely Loves the Songcraft of “The Gambler” but Cannot Effectively Argue That Point to His Target Audience Without Contriving Complex Framing Devices With Which to Swaddle His Cover of It Doughty isn’t good about putting words in a straight line—if he were alive three generations ago he’d be writing Dadaist sound poems. The whole point of Soul Coughing’s lyrics were words that sounded fun and rubbery bouncing off the beats, and now that he’s kinda-sorta a singer-songwriter he’s having a tough time making a simple point. “Busting Up a Starbucks” isn’t about that, really, and no song with the word “decathecting” in it is going to get into the Nashville Songwriters Foundation Hall of Fame. Incapable of being so articulate himself and desperately needing to, he reaches for the simplest tune he can think of. And when he finds one, he’s gonna hang onto it for a while. Mike Doughty knows when to hold ’em.