Over wine, Prosecco and a delicious meal, five music professionals laughed and clapped through a stellar performance by longtime outlaw Billy Joe Shaver and his band, which this night included Willie Nelson’s harmonica wizard Mickey Raphael.

Just off his taping for the Late Show With David Letterman earlier in the day, Shaver treated a sold-out house to his classics like “Georgia on a Fast Train” and “I’m Just an Old Chunk of Coal,” interspersed with cuts from his recently-released Long In The Tooth album, nearly 30 songs in all. When singing “Hard To Be An Outlaw,” the album’s first track and a duet with good friend and fellow miscreant Willie Nelson, Shaver broke up the lyrics, saying “This is Willie’s part,” and remaining silent in the space where Nelson would have been singing. The lyrics say, “It’s hard to be an outlaw who ain’t wanted anymore,” but it’s tough to reconcile that concept with a sold-out show and two national TV performances in one week (Nelson also performed on The Colbert Report).

Now 75, Shaver kicks a little lower than he did before knee surgery, but his shows remain dynamic and his bad-boy ways seem intact. He often moves from song to song immediately, but it’s also not unusual for him to interject a ten-minute story to explain the origin of a four-minute song either, and each story is better than the last. Famously thrice-married and thrice divorced to each of two women (that’s six times total, folks), Shaver quipped, “Marriage is a great institution, but who wants to live in an institution?” Joking with his Hispanic bassist Nick Gaitan, Shaver said Gaitan translated “La Quinta [Inns]” to mean “behind Denny’s,” and then went into a lengthy description of his own après-drinks shooting incident and subsequent acquittal on all charges—age 70 and still popping off.

I got home just in time to see Shaver and Nelson on Letterman—exactly the band I’d seen at City Winery, plus Nelson actually singing his part. When it comes to hearing Shaver, though, twice a night ain’t too much.

– Suzanne Cadgène