5 Things We Learned From Loudon Wainwright III's Intimate NYC Show

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While many practitioners the singer-songwriter genre in the '70s approached politics, love, and self-examination with the deadly seriousness the singer as The Artist, showing the full range human emotion was never a problem for Loudon Wainwright III.

Although hailed as a 'new Dylan' when he debuted, Wainwright was far more comfortable indulging in self-effacement and even a goy side, unabashedly going for laughs with his wry lyrics and winking delivery. Of course there were serious autobiographical songs about sadness and failures, but he never bothered fostering that marmoreal cool so many did in the post Dylan scene, skewing closer to musical humorists like Tom Lehrer. That helped endear him to a cultish following as well as famous fans such as Johnny Cash (who covered "The Man Who Couldn't Cry" on American Recordings) and Judd Apatow (who is producing his upcoming Christopher Guest-directed Netflix special Surviving Twin based on his one-man show about his late father, a Life magazine columnist).

Wainwright's penchant for performance was on full display Monday (July 16) night at the intimate Caveat (a self-proclaimed "bar for intelligent nightlife") in Manhattan. In conversation with fellow artist Chuck Prophet, Wainwright spoke on his upcoming two-disc release Years In the Making, a collection 42 unreleased and rare tracks spanning 45 years. His eclecticism is nodded to in the packaging the set, which segments his songs into seven "chapters" such as folk, rock, kids, "love hurts" and more.

In between reminiscing about his childhood friendship with Liza Minnelli or the recent Wainwright Family tour Alaska, the 71-year-old performed several songs from the upcoming Sept. 14 release, either alone with his guitar or with a banjo player and violinist backing him. Throughout it all, Wainwright was cracking jokes and flashing smiles like a born entertainer -- hell, he was even wearing seersucker pants.

Here are five things we learned from his Caveat appearance.

Rockin' With The Band

Upon record industry legend Clive Davis' suggestion, Wainwright branched out and recorded songs with rock musicians backing him during the '70s. And one those bands was, well, The Band. Years In the Making will feature vintage material Dylan's former backing band teaming up with the erstwhile 'new Dylan' Wainwright – but just the highlights. "We picked the good Band stuff," Wainwright told Prophet, adding, "There is bad Band stuff."

How Liza Minnelli Factors Into All This

As recounted in his autobiography Liner Notes, Wainwright was childhood friends with Liza Minnelli and once went over to her house (yes, he met Judy) where he played chauffeur to her starlet when they were very young. After his family moved away and a letter to her went unanswered, they lost touch until he sang about her on 1973's Attempted Mustache on a song aptly named "Liza." Still no reply. Later, a journalist sat down with Minnelli, played her the song and asked for her thoughts, to which she replied, "He'll ruin his voice if he keeps singing like that." That interview will be included on Years In the Making, to which Wainwright quipped, "I expect I will be sued."

Folk Trio Protest Time

In 2018 we've collectively come to terms with the fact that guitars don't exactly kill fascists, but they can provide a spiritual balm during tough times and keep you from feeling totally alone in the universe. So it was only fitting that on a day when Trump was accused treason against the country he's ostensibly in charge , Wainwright would deliver a topical song. But for Trump, a sanctimonious, preachy takedown just doesn't work; cue a hoppin' country-folk number delivered with a pained smile. Rhyming "dread" with "Feb" and including lines like "There’s a reckoning coming in November they say / until then it’s to Robert Mueller we pray," Wainwright's recently written "Presidents' Day" is an old-timey, one-liner-stuffed protest tune that fits 2018 like a glove on a very tiny orange hand.

Meet the Wainwrights

A few years back, Loudon hit the road in Alaska for a tour with son Rufus, ex Suzzy Roche, sister Sloan and daughter Lucy Wainwright Roche billed as the Wainwright Family Alaskan Adventure. To commemorate the event, he wrote a straight-up ditty about their less-than-perfect family dynamics that lovingly pokes fun at Rufus for being much more rich and famous than the rest. He also throws back to his 1975 song "Rufus Is a Tit Man" (about breastfeeding) to acknowledge the eventual irony in that title: "Once was a tit man, now he checks out pecks." The version on Years In the Making features playing and singing from his family, including Martha, who was unable to make the original Alaskan trek.

Retire? Who, Me?

Before singing the gentle meditation on mortality "Out This World" (Years In the Making's penultimate track), Wainwright answered a question about how long he'll be doing this. "It's too late to stop now, as Van Morrison so aptly put it," he answered.