Still sharp-eyed self-analysis

Tucked away on the DVD in the new Loudon Wainwright III boxed set 40 Odd Years, there's a video of "The Home Stretch."

It's the song where the middle-aged troubadour gets down in the dumps, weary of the road, and takes little solace in telling himself "at least you're a has-been, and not a never-was." Things are so bleak for the autobiographical singer-songwriter that "You've stopped writing songs / There's nothing left to say."

Wainwright penned that one in 1986, 25 years ago and a mere three-eighths of the way, chronologically speaking, into 40 Odd Years (Shout Factory ****). The five-disc compendium came out last week, as did Tell My Sister (Nonesuch ***½), a three-disc set that looks back on the career of Kate and Anna McGarrigle and includes two Wainwright tunes. Kate McGarrigle, who died last year, was Wainwright's first wife and the mother of his music-making children Rufus and Martha.

Suffice it to say, the self-pitying writer's block that inspired "The Home Stretch" didn't last long.

Since that excellent song, the now-64-year-old LW III has written many, many more equally good ones.

There are songs on 40 Odd Years about being a father ("A Year," "When You Leave," "Bein' a Dad"), and being a son ("Surviving Twin," "White Winos," "4 X 10"). Amusingly astute songs about public figures ("Newt," "Tonya's Twirls"), and heart-tuggers about holiday celebrations ("Thanksgiving," "Christmas Morning"). There are kind of creepy chuckle-inducers about trying on your girlfriend's clothes ("When I'm at Your House") and stop-cold-in-your-tracks confrontations with mortality (the chilling new "Dead Man").

And here's the thing that sets 40 Odd Years, and Wainwright's ongoing career, apart: As the set goes on - leaving behind the period when the son of Life magazine journalist Loudon Wainwright Jr. experienced the success of his one hit, "Dead Skunk," in 1972 - it doesn't just hold its own.

It gets better.

And as the first- and second-generation songwriters of the rock era have aged to the point that they now qualify for Social Security, who else can you say that about?

Wainwright is that rare artist whose new songs - like the harrowing "Middle of the Night," on last year's 10 Songs for the New Depression - are every bit as good as his old ones, like "School Days," the confessional about going to prep school at St. Andrews near Townsend, Del.

Wainwright never earned the combination of sustained universal acclaim and mainstream success that contemporaries like Neil Young, Bruce Springsteen, and Joni Mitchell did, and maybe that has fueled an obsessive drive to get his due. Or maybe it's that, as he has gotten older, his great subjects - family, unsuccessful relationships, and "death and decay," which he identified as his current favorite topic during a recent show at Philadelphia's World Cafe Live - have provided ever more grist for his sharp-eyed, self-analyzing songwriting mill.

Songwriters and artists of all stripes love to talk about how, like Bob Dylan, they don't look back, and instead focus on the next creative project. Usually, that's at least a partial lie. If you don't give the audience the oldies they demand, you soon won't have an audience.

Wainwright isn't entirely immune to that syndrome. If he were, there would be no 40 Odd Years, which tracks his career over three chronological CDs, augmented with a disc of rarities and the DVD. The last includes a fascinating 1993 documentary made for Dutch television, One Man Guy, that includes unguarded interviews with the family members whose lives Wainwright has been exploiting for decades for his own creative ends.

The boxed set pays deserved attention to a body of work that rewards it, and it clearly means a great deal to Wainwright, who made the song selections himself. In the liner notes, he compares leaving off cherished songs to "drowning kittens."

But that doesn't mean he's about to start dwelling on the past - unless it's in a song that explores how he feels in the here and now. When he played the World Cafe last month, not only did he hardly draw from the songs in the boxed set, but he didn't even mention its existence.

Begrudgingly, he did a few old songs that are on it, by request, like "Men," the a cappella rumination on vulnerability and machismo originally on History, the brilliant 1992 album that explores memory and loss and familial complication with near-perfect emotional pitch. (In the notes to 40 Odd Years, Wainwright writes of History that its songs "came after my father's death, in the same way that the songs for [2001's] Last Man on Earth came after the death of my mother. Somehow, those huge losses gave those records special power and resonance.")

The two Wainwright songs that turn up on Tell My Sister, both sung by Kate McGarrigle, fit in nicely. The first is the banjo-flailing "The Swimming Song," a highlight of the Quebecois siblings' 1975 self-titled debut and one of Wainwright's best-loved songs. The other is the lesser-known "Over the Hill," a touching lament with an inviting melody written in the voice of a regretful old man by a songwriter then in his 20s. (It's on the Sister set's third disc of often-luminous rarities assembled by Joe Boyd, who produced Kate & Anna McGarrigle and its brittle, beautiful 1977 follow-up, Dancer With Bruised Knees.)

But while the McGarrigles and Wainwrights are forever linked, it's not as though the sisters needed Wainwright's assistance. With songs like the debut album's jaunty yet fatalistic "Kiss and Say Goodbye" and their best-known song, "Heart Like a Wheel," which was a hit for Linda Ronstadt, the sisters expertly updated North American folk and parlor-song traditions to their own original ends.

Kate McGarrigle has come to be seen as both the wronged woman in Wainwright's more mean-spirited songs and a sort of sainted maternal figure in one of the great families of folk music, particularly since her death inspired their son Rufus Wainwright's somber All Days Are Nights: Songs For Lulu last year. She's also the subject of Emmylou Harris' "Darling Kate" on her new album, Hard Bargain.

Tell My Sister, though, captures the McGarrigles in their prime, when they made their own brand of frisky, tough-minded, and sexy folk music. The sisters recorded infrequently and unevenly after their '70s heyday, but this reissue brings their music back to life and shows what a high standard the generation that followed has to live up to.