This piece is part of the Detours series. Detours are deep dives, because music deserves time and context. Listen, breathe deep, take the scenic route.
An album titled The Honesty Room seems to promise authenticity. But even with such expectations from the start, I find Dar Williams’ 1993 debut remarkably honest.
Williams has been called one of “America’s very best singer-songwriters,” and she’s also one of my very favorite singer-songwriters. She grew up in New York’s Hudson Valley and went to Wesleyan University (if this song didn’t make that obvious). She’s released nine albums, not including a collection of live recordings and a greatest hits compilation.
Williams is one of my dad’s favorites too, and her music played in the background of a lot of my childhood. Once I rediscovered her music in college, I tried to listen to her discography slowly, so that I wouldn’t run out of it too fast. I started with The Honesty Room, Williams’ first full-length album. The record has now come to represent, in my mind, my transition from about age 10 to 22, growing up in southern Minnesota. I grew up in a small college town called Northfield with a lot of farms and a charming collection of locally-owned businesses lined up along one main street.
I remember being a kid and hearing “When Sal’s Burned Down,” the fourth track on The Honesty Room. The lyrics tell the story of the demise of a small-town bar. When my dad told me what it was about, I remember feeling disturbed. A song about a building burning down?
But when I listen to it now, I think about the culture of small towns—the way they lend themselves to characters, how they crave stories, how some community cornerstones last while others fade away (the opening line is so good: “Are we the fools for being surprised that a silence could end with no sound?”).
Part of why The Honesty Room speaks so well to my understanding of my own upbringing is that Williams spends much of it discussing her own. On the fifth track, “The Babysitter’s Here,” Williams sings from the perspective of a child in awe of her very cool babysitter, who has to choose between college and some boyfriend.
Her boyfriend is Tom but we call him "the king of romance”
He wears an American flag on the butt of his ripped up pants and
Will they get married with kids of their own
He says "Not if she's going to college we won't"
and he kisses her, oh, someday I'll have a boyfriend just like that
She’s the best one that we’ve ever had
She sits on her hair and she's tall as my dad
And she got mad at dinner when Tom drank a beer
But peace man, cool hey, the babysitter's here
When my family moved from the suburbs of Minneapolis to Northfield I was in sixth grade. I was right on the cusp of being independent enough to be home alone, and I was babysat only once after the move. I remember how it felt, and how I didn’t like the babysitter, because she just sat on the couch and texted while my sister and I played a board game. I thought she seemed like a high-schooler in a bad way, not at all like Dar’s babysitter.
And if my high-school boyfriend had told me I had to choose between him and college, I wouldn’t have had to, because I in fact picked a college conveniently located in Northfield. (I did break up with him anyway, though.) I was an adventurous person, or at least knew I could be, but I also loved the school and was convinced it was perfect for me, despite its major drawback of being in my hometown. But I always felt a little defensive about that.
On the song’s last “She’s the best one,” Williams really punches the “she’s” with a high-pitched, childlike earnestness. And later, when she describes watching her babysitter perform in a high school play, she interjects “I can’t wait to give her the card” between verses, but more like “I can’t waittogiveherthecard”—stumbling over her own words in her excitement.
I’ve never regretted my college choice. But because I was so close to home, I drew a hard line when it came to seeing family: we weren’t going to see each other any more than we would if I’d chosen an East-coast school. Even when we ran into each other accidentally (it was a small town), I’d hastily wrap up the interaction. And when my sister starred in her final high school theater performance, I didn’t go, because “I wouldn’t have been able to go had I gone to [insert any other school I’d been considering].” I wasn’t even busy that night! It was just the principle. That’s a decision I do regret.
“The Babysitter’s Here” is the only track on The Honesty Room sung from a child’s perspective, but childhood is a theme throughout. The very title of the album feels somewhat childlike. “The Honesty Room” not only signals the album’s sincerity—it also sounds like a place a mom might send her fibbing child. But as a room, the album is inviting. There are cushy couches, dim light, a fireplace, pads of paper and pens and coloring books scattered around the carpet.
The Honesty Room has two songs called, parenthetically, “Traveling, Pt. 1” and “Traveling, Pt. 2.” Notably, part one is titled “Traveling Again,” which I get a kick out of. As the eighth of fourteen tracks, it’s an excellent crease for the album. Its tempo feels like prancing along, traveling to the next half of The Honesty Room. Williams sings: “Not driving away from myself / It’s just myself drove away from me.” It’s such a cerebral line—almost silly in its self-consciousness. One of Williams’ great strengths is her ability to straddle the line between silliness and wisdom.
In the preceding track, “You’re Aging Well,” Williams leans more toward wisdom, but with an image-heavy, almost mystical frame.
It’s my favorite song off the record, and I think it captures The Honesty Room as a whole: introspective, gentle, vulnerable, and vivid. It feels like it’s sung by a grandmother and also by a twelve-year-old, simultaneously.
“You’re Aging Well” was the first Dar Williams song I latched onto during my rediscovery of her music. I think of it as a “rediscovery” because, though her music had been present throughout a lot of my life, it had always served as a backdrop. I never sought it out on my own, I’d just hear it when it was on in the car, or coming from the kitchen. Then suddenly during freshman year of college, a professor had one of her songs playing at the beginning of class one day. I was totally transported, and I dove into her discography to get to know her on my own. I’d listen to “You’re Aging Well” as I walked around campus in the nighttime, knowing how close I was to home, but also how distant I’d made myself from it, figuring I could trust Williams when she said I was aging well, since she’d been there as I’d grown up.
But one voice got through, caught her up by surprise
It said, “Don't hold us back, we're the story you tell,”
And no sooner than spoken, a spell had been broken
And the voices before her were trumpets and tympani
Violins, basses and woodwinds and cellos, singing
“We’re so glad that you finally made it here
You thought nobody cared, but we did, we could tell
And now you'll dance through the days while the orchestra plays
And oh, you’re aging well."
This orchestra feels present again in the album’s closing track, “Arrival.” “You finally made it here” echoes throughout the choruses of “You’re Aging Well.” So the title “Arrival,” on a track swelling with strings, leaves me feeling pretty convinced that I did make it there—even though I’m not sure where exactly that is.
Williams majored in theater and religion, which feels fitting. Her liberal-arts, small-town-campus background might help explain why after a few decades of making folk music, she decided to write a book—not about her career as a musician, but rather a sociological look at America’s communities. It’s called What I Found In A Thousand Towns, and it’s about small towns—how they can build connection, use public spaces, and foster thriving community.
In the fall of my sophomore year, Williams stopped in St. Paul on her book tour. I made what would be the first of many exceptions to the hard-and-fast rule I’d set for myself and drove up to the cities with my dad to see her talk.
The bookstore was absolutely packed, so my dad and I sat on the floor, behind all the people enjoying plush, privileged views in their folding chairs. Williams read from the book, including a special passage about Minnesota, which she told us she’d had to cut from the book simply because it would “make all the other states jealous.” That’s just the kind of thing Minnesotans love to hear!
Then there was a signing, where I said something that instantly felt kind of dumb. I thanked her for coming, and asked: “Are you still making music?” Because that was what I wanted to know! Because nine albums isn’t enough for me! And she replied: “Well, yeah—I mean, I just had an album come out.” She was referring to 2015’s Emerald, which I of course knew was out! Then I thought I should have crafted a more intelligent question about her music. Maybe about the lyrics to “As Cool As I Am.” Or maybe she didn’t find my question annoying at all.
She drew a lovely, wonky-looking smiley face in my book. Ultimately, it feels only right that our interaction left me feeling a little embarrassed—it was perfectly honest, even childlike. And if book-touring, still-making-music Dar thinks I don’t really understand her career, that’s okay, because surely the Dar whose voice was the soundtrack to both my childhood and college years understands what I meant.
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