Loudon Snowden Wainwright III had big shoes to fill even before he became a Grammy winner. His father, Loudon Wainwright Jr., was an editor and columnist for Life magazine — his weekly rumination under the title “The View From Here,” on the last page, was the first thing I turned to when I was a kid. (OK, I’m a geek.) It wasn’t until 1962, when my brother Mark began his five-year stint at St. Andrew’s School in Middletown, Delaware, that I connected Loudon the elder with the quirky, rubber-faced musician I’d see in staged events from time to time — Loudon the younger. It’s the same school where Dead Poets Society was filmed, and according to Wainwright’s eponymous debut album, he didn’t have an overly positive experience there. “School Days,” the first cut on that album, is a bitter denunciation of the elitist mini-society around him. His pose then was cool rebel, brooding literary nerd and he hasn’t strayed too far from that stance in the 50 years since.

Excepting his 1972 novelty hit song, “Dead Skunk (in the Middle of the Road),” his mostly acoustic style of music has reflected his displeasure with the status quo and his own peccadillos, including depression, marriage, being a father — his kids with first wife, the late singer/songwriter Kate McGarrigle, are Rufus Wainwright, the mega-talented singer/songwriter, and Martha Wainwright, also a singer/songwriter. All these singer/songwriter designations seem to demand that the so-designated live up to it; Wainwright has made more than 20 albums, three of which were nominated for a Grammy. His 2009 effort, “High, Wide & Handsome: The Charlie Poole Project,” won a Grammy for Best Traditional Folk Album. The double CD (booklet included) is an homage to Poole, who didn’t write his own songs but popularized his versions of folk songs of the day. It includes Wainwright’s original songs, too, written with producer Dick Connette. It’s a fascinating glimpse into what makes Wainwright keep going: music about regular folks living a regular life. In the ’20s and ’30s in the rural South, that often meant a hard life for Poole, filled with booze-soaked nights at honky-tonks and sweat-filled days working in the mills. Wainwright can relate. He was born in Chapel Hill, North Carolina and despite his Bedford, New York and prep school upbringing, identifies with the South, at least as far as his music goes. The Poole album in particular reflects much of Wainwright’s own style — humorous, simple lyrics, delivered with a rather snarling, smart-ass attitude, cooled every now and then with a sweet, emotional and heartfelt ballad.

Wainwright was instructed by his famous father to stay disciplined, and deliver the goods on time. Certainly St. Andrew’s School’s rigid environment added to that work and study ethic, and Wainwright toes the line, whether acting (he played the “Singing Surgeon” on many M*A*S*H episodes and has been in several films), performing on stage with various family members, or turning out deeply personal, yet universally relatable album after album.

His appearance here on Friday, Dec. 11 at Ponte Vedra Concert Hall is eagerly anticipated by his many fans, and should be attended by anyone who enjoys political commentary, personal anecdotal lyricism set to catchy tunes, and lovely ballads. His song topics run the gamut from gun control, heartbreak, drinking, growing old and, as I read on the venue website, “ … pet ownership and New York City’s arcane practice of alternate side-of-the-street parking.” Since it’s the holiday season, look forward to his “I’ll Be Killing You This Christmas,” sure to become a standard classic covered by the likes of a Michael Bublé or a Sam Smith for years to come.

Loudon Wainwright III has lived a full life and got most of it down on tape or wax for us to enjoy. I hope he continues to put his innermost fears and joys out there for many years more.

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october, 2021