loudon proud

That’s Loudon Wainwright III crying. But don’t be sad for him. He’s fine! Better than fine, really. He released his 20th studio album,  High Wide & Handsome: The Charlie Poole Project, on Tuesday. (Well, sort of, but we’ll get to that later.) These days Wainwright is probably best known as the pater familias of the musically inclined Wainwright clan – his son is Rufus, his daughter is Martha, and his ex-wife is folk singer Kate McGarrigle – but the man is a towering statue in the museum of emotive ’70s singer-songwriter types. Just look at that beard. But Wainwright is a swirl of wit, too, like a Northeastern Randy Newman. And if he’s not just a famous Dad, he’s also a “famous Dad,” carving out a place for himself in Hollywood as an earnest, cheery father-type in Judd Apatow’s dearly departed college sitcom “Undeclared” and as an intransigent father in Cameron Crowe’s regrettable Elizabethtown.

High Wide & Handsome is kind of a headslapper for Wainwright, who has found ways to be funny and tender and callous all at once throughout his career, just like Poole. It’s a nice entree to Poole’s protocountry sound – beware all the fiddle here – plus Wainwright delivers some originals of his own. The elegiac “Old and Only in the Way” – a crushing splash of teardrops about the perils of the geriatric – is a highlight, performed with his kids, Rufus and Martha. But to hear Wainwright working strictly in this vein is ultimately a bit disappointing. It feels constrained and a little shticky. (There’s an insightful interview with Loudon over at NPR’s Fresh Air right now, ready for streaming.)

Fortunately, eMusic has got nearly all of Wainwright’s essential albums. Wainwright started his career, as Robert Christgau once wrote, “as a failed poet.” His first two albums, while smart, and emotionally translucent, seem to be searching for some higher meaning. It wasn’t until Album III that Wainwright chilled out and started making fun of himself and everyone else. The album kicks off with what is probably his best-known song, “Dead Skunk,” an amazingly catchy and jokey song that appears to be about almost nothing. Listen again. On III he found ways to be self-revealing, as on regretful but weirdly bouyant “The Drinking Song,” without being mawkish.

I was gobsmacked by Wainwright for the first time when I saw 2005’s The Squid and The Whale, which used his “The Swimming Song” as a sort of theme. The song was a hit for him in 1973, from the stellar Attempted Mustache (amazing album cover, no?). “The Swimming Song” is another example of this lighthearted nostalgia that permeates Wainwright’s best songs. Ditto the mordant “Bell Bottom Pants” which opens with a doleful remark: “This song is dedicated to the United States Navy.” Perceptive, punchy, pure wiseass, that’s Wainwright. “Liza” – an a capella ode to his 3rd grade classmate Liza Minelli – feels plainspoken, but it’s even harder to parse.

We’ve also got Arista’s doubling up of 1976’s T Shirt and 1978’s Final Exam, where Wainwright ditched the lone-ranger-with-a-guitar thing and introduced a full band while pushing bigger, bolder arrangements. “The Heckler,” in particular, is like something out of a Derek and The Dominos lost session, minus the gloopy “I love yooouu” sentiment. Alas, the albums struck just as punk was getting its legs – Nevermind The Bollocks, Here’s The Sex Pistols was released in between the two albums – and Wainwright’s ambitions were dissed and dismissed as haughty with too much fat on the edges.

I say Wainwright only sort of released his 20th studio album this week because a handful of his LPs pioneered a strange trend wherein he performs half of the songs in a recording studio and the other half in a live setting. This makes some of his work uneven, but it also shows a guy deeply comfortable cracking jokes about his son’s breastfeeding proclivity on “Rufus is A Tit Man,” from 1975’s Unrequited, in front of hundreds of people. But this can be a trap. For an artist so open about the impossibilities of parenting, he loves to take the occasional shot too far. It’s his biggest problem: Say something fucked up for a laugh, then backtrack and realize the pain caused.

In recent years Wainwright has had a creative resurgence, forming a partnership with Joe Henry and working with the filmmaker Apatow on a quasi-soundtrack to his hit, Knocked Up, which is here as Strange Weirdos: Music From and Inspired By Knocked Up. Last year he recorded Recovery, a rerecording and reconsidering of some of his best songs, including personal favorites “Black Uncle Remus” and perhaps his greatest, “The Man Who Couldn’t Cry.” Wainwright sounds quieter, less cheery here – almost as though the jokes he wrote as a twentysomething have somehow turned cruel. He’s growing older, wiser. Maybe better, too.