(Pictured: country singer Don Williams, 1980)

When I was a country DJ back in the late 70s and early 80s, Don Williams was one of my favorite singers. While other country stars churned out singles as if they were stamped out of a form, Williams’ records seemed more carefully made, with deeper lyrics and greater emotional resonance. He didn’t write many of his biggest hits—that list is otherwise studded with the work of Bob McDill, Wayland Holyfield, and Roger Cook, as well as John Prine, Dave Loggins, and Don Nix. But once he sang a song, in that big, warm, grandfatherly voice, it belonged to him.

Williams’ tally of hits is remarkable. He first charted in 1973, and he scored his first Top 10 with “We Should Be Together” in 1974. His next 32 singles would hit the Billboard country Top 10, and he would add 16 more between 1985 and 1991. In all, 17 would hit #1 on the country chart, including his version of Eric Clapton’s “Tulsa Time” in 1979. His biggest country hit, 1980’s “I Believe in You,” crossed over to the pop chart and reached #24. As country fashions changed in the 1990s, Williams fell out of favor, and he hasn’t charted a single in the States since 1992. He released an album every couple of years until 2004, but not again until 2012. Just this year, he released another, Reflections. At age 74, he’s one of those guys who seems as though he’ll keep doing what he’s always done forever, because he’s earned the right, and he’s damn good at it.

The song I want to write about here, however, is an anomaly. It’s the one that broke his decade-long streak of 33 straight Top 10s 30 years ago this fall. At first, you’d be forgiven for thinking “Maggie’s Dream” is just another song about a truck-stop waitress. She goes to work every day, banters with the truckers, collects the tips they leave, and dreams “a dream she’s had since she was 17 / To find a husband and be a wife.” But because one of Don Williams’ gifts is infusing a song with emotional subtext far beyond the mere words on the page, you soon realize there’s much, much more going on.

The mountains around Asheville
She’s never seen the other side
Closer now to 50 than to 40

I know a few things about music, but I don’t know the first damn thing about songwriting. I do know that what Dave Loggins and Lisa Silver do on “Maggie’s Dream”—or maybe it’s how Williams and his co-producer Garth Fundis decided to arrange it—packs a remarkable emotional wallop. I don’t know if you can call it a bridge or a middle eight or a verse performed differently or what it is precisely, but it comes at the very of the song. And given what we have learned about Maggie, and the mood Williams has created, it’s devastating:

And she relies upon the jukebox
0n the lonely afternoons
When the business starts to slow down
She plays the saddest tunes
And she stares off down the highway
And she wonders where it goes
Nobody to go home to
And it’s almost time to close

As we listen to the instrumental fade, and we watch Maggie looking out the window down the North Carolina highway, we realize what she must surely know—that the life of which she dreams will remain as mysterious to her as the other side of the mountains. That her dreaming will be as endless as the highway.

We don’t know the time of year in which “Maggie’s Dream” is set, but it’s got to be October.