“75 is a big number,” says Loudon Wainwright III.

He's referring to the age he recently turned, as well as “How Old Is 75?” one of the many beautifully reflective songs on his latest release Lifetime Achievement. Milestones aside, the truth is that Loudon has always been a keen observer of his own aging process, documenting it with an honesty that few songwriters would dare use.

“I've kind of been obsessed with my numbers all the way along the line, you know?” Loudon says. “I have a song that I wrote in 1972 called 'New Paint,' which is about a guy trying to pick up a girl in a park, saying 'If I was sixteen again.' I wrote that when I was twenty-five. I had 'Watch Me Rock, I'm Over Thirty.' I had a song, 'The Birthday Present,' that I sang a capella in a shower about hitting age 50. So 75 is a new number, but it's just another number.”

Maybe, but what makes it remarkable is that after thirty albums, countless concert appearances, a Grammy, many film and TV roles, and songs recorded by such artists as Johnny Cash, Mose Allison, Bonnie Raitt and his son Rufus, Loudon sounds as engaged and passionate as ever. His singular talent as our foremost six-string analyst and tragicomedian extraordinaire is not only undiminished, but hitting new heights of what NPR calls his “unmatched wit and wisdom” on Lifetime Achievement.