It's hard, at first, to draw a straight line between the raunchy geekitude of movie director Judd Apatow and the wry, literate style of folk balladeer Loudon Wainwright III. But when you listen to Strange Weirdos—Wainwright's 2007 album, recorded for and inspired by Apatow's hit comedy Knocked Up—the creative parallels between the two emerge. For both Wainwright and Apatow, wit is the primary weapon, but it's always complemented by an underlying sincerity and sweetness.
In the liner notes to Strange Weirdos, Apatow recalls seeing Wainwright on Late Night With David Letterman in the early 1980s, singing a song in which he threatened to commit suicide just to make his ex-girlfriend feel guilty. "I was hooked," Apatow writes. It would be 20 more years before Wainwright would first hear of Apatow, but the experience was similar.
"The first time I heard about him, I was contacted about doing an acting job with his show Undeclared," says Wainwright, speaking on a cell phone in transit from Ann Arbor, Mich., to Kent, Ohio. "I hadn't seen [Apatow's series] Freaks and Geeks, but they sent me tapes of it, and I watched it and immediately liked it very much. I liked the writing and the whole slant of it. So I was excited to meet Judd and very happy to get to work with him."
Wainwright popped up again with a cameo as a priest in Apatow's breakout film, The 40-Year-Old Virgin. You can spot him as a doctor in Knocked Up, as well, but his greater contribution is the film's music, particularly the opening and closing credit songs, "Grey in L.A." and "You Can't Fail Me Now." The former is a sardonic tune about the benefits of bad weather; the latter is a heartfelt love song as solid as any Wainwright has penned in his nearly 40-year career. Like most of Strange Weirdos, these songs stand on their own, even without the film's context. But writing with the film in mind did prove to be a departure from Wainwright's usual process.
"Well, I worked on Strange Weirdos with my friend and songwriter Joe Henry," he says. "And because we are songwriters first, when we got the job, we just wrote a bunch of songs, some of which were used in the movie. Others weren't. Pieces of them were used instrumentally in parts of the movie, too. So, it was a bit different, because usually when you make a record, you're the decider, so to speak. But Judd Apatow, as the director and writer of Knocked Up, gave us the job, and so all the final decisions about the music—in the movie, anyway—were his."
Despite the massive success of Knocked Up and the positive reviews for Strange Weirdos, Wainwright remains a folk hero on the fringes of the mainstream. He's better known by some as the father of equally acclaimed singer/songwriters Rufus and Martha Wainwright. As if that weren't enough talent to bestow upon the Earth, Loudon is currently sharing the stage with yet another of his children, 26-year-old Lucy Wainwright Roche, the product of his second marriage (with singer Suzzy Roche). For much of his time on the road, though, Wainwright is still a "one-man guy," touring from town to town much as he has since his days as a New York folkie with Atlantic Records in the early '70s.
"It's much the same, in fact," he says. "It's getting from A to B in a car, like I am today, or on an airplane sometimes, with my guitar, and showing up and doing a show. I mean, I'm older, so I don't move through the airports as quickly. But the job description of being a performing one-man band has basically remained the same in the last 35-plus years."
Keeping with that theme, Wainwright never hesitates to reach back a few decades or so in his current live sets.
"Well, I've written a lot of songs over the years," he says, "and it's fun to go back and relearn some of the old ones and do them. Last night, I sang a song from back in 1972 called ‘New Paint' and another one called ‘Muse Blues.' My daughter and I sang a song called ‘Needless to Say,' which was the B-side to my hit single ‘Dead Skunk.' So, yeah, it's always fun to go back and revisit those...classic oldies."