Loudon Wainwright III: A Lifetime of Achievements

The global events of the last few years – global pandemic, political unrest, a brutal war in Europe – could provide more than enough motivation for a songwriter to create a bumper crop of songs focusing on the negative, the downcast, the pessimistic side of life. But even though he’s long been known for his keen and observant songwriting approach, revered troubadour Loudon Wainwright III tends toward a wryly humorous approach in his work. So even against the backdrop of worldwide calamities, his latest album, Lifetime Achievement is a collection of upbeat and optimistic songs that provide some welcome light amid the darkness.

Wainwright readily concedes that the pandemic was a terrible occurrence. “But for me personally,” he says, “it wasn’t bad; in some ways it was good.” Wainwright spent most of the lockdown period at his home on the eastern end of Long Island, New York, with his girlfriend and their two cats. “Susan couldn’t go to her office, and I don’t have an office to go to,” he says. “So we spent a lot of the three years here on this island, and on a good day, it was a beautiful thing.” Along the way he endured a mild case of Covid, but for him, that was the worst of it.

Wainwright wrote a batch of new songs during that time, and when it came time to record them, he decided to employ a spare approach. “I’ve made a lot of records,” he points out. “25 or 30; I don’t even know how many. And I’ve done them a lot of different ways.” Some of Wainwright’s albums have found him backed by a rock band; others used jazz players. Some were big studio affairs; others, simple, homespun and intimate records. “It’s been kind of a checkered career,” he says.

The songs often dictate the kind of aesthetic each of his albums should have, Wainwright suggests. For Lifetime Achievement, “we decided originally to keep it super-simple: voice and guitar,” he says. “And I think that was the correct choice. For this record, anyway.”

A couple of songs on Lifetime Achievement do feature a full band. “’Town & Country’ is pretty rocked-up,” Wainwright says, and the title track “has all kinds of various [instruments] on it.” But that unadorned and straightforward approach characterizes the album.

Considering his body of a work as a whole, it’s tempting to label Loudon Wainwright III a prolific songwriter. But he’s not sure that description is an accurate one. “In the beginning of my career, I was writing three to four songs a week,” he admits. But these days, he says that it takes him several years to gather together a group of songs. “I liken it to sex,” he says with an impish grin. “When you’re young and happening, it just keeps coming. But now…”

For Wainwright, quality wins out over quantity. In normal times, he might road-test new songs, trying them out in front of audiences to see how they land, tinkering with them as needed before taking the songs into the recording studio. “That’s the finest litmus test,” he says. “See if it works, see if there are laughs in it, see if I get the laughs, see if the song itself works emotionally with an audience.”

With the worst of the pandemic now receding into history, 76-year-old Wainwright is back on the road. But only now is he getting the chance to play his new songs in front of a live audience. “During the pandemic I created a couple of virtual shows,” he says. But without the feedback that comes from singing and playing music in the same room as people who are watching and listening, he didn’t have that real-time feedback at his disposal. “So,” he shrugs, “I just had to assume they’re good songs.”

Wainwright – whose career includes many acting credits in movies (M*A*S*H, The 40-Year Old Virgin) and television (Ally McBeal, Parks and Recreation), began his career as a recording artist with a self-titled album in 1970. Asked what the young man who wrote melancholy character studies like “Hospital Lady” and the wacky singalong “Dead Skunk” (from 1972’s Album III) might think of the 2023 version of Loudon Wainwright,” the quick-witted songwriter is momentarily stumped.

“When I was starting off, I was a young guy full of beans and ambition and dreams,” he explains. “I couldn’t imagine that I would be doing this as a 75, 76-year-old man. But, as it turns out, I am and did, so look what happened.”

You may also enjoy my 2016 interview with Wainwright.