#120, "You're Gonna Make Me Lonesome When You Go," Bob Dylan (1975)

150 Favorite Songs: #120, "You're Gonna Make Me Lonesome When You Go," Bob Dylan (1975)

I mostly used up Blood On The Tracks when I was nineteen. I wanted to believe that I could really relate to Bob Dylan's soundtrack to a mid-life divorce at that point, because every little heartbreak feels that big when you’re a teenager. I gravitated to the most overwrought songs, of course—"Idiot Wind" and "Simple Twist Of Fate" and "If You See Her, Say Hello"—so "You're Gonna Make Me Lonesome When You Go" mostly didn't register. He sounded kinda...happy, and who has room for that when you're mourning the fact that Kalee doesn't like you back? 

I didn't realize until much later that this song is kind of the saddest of them all. It's so transitional, and knowing the story behind it just confirms that. (The short version: right after the divorce, Dylan started dating a much younger woman—shocker, that—and it was nice, briefly, until it ended as rebounds do.) The thing that makes it so sad is that the song isn't "you're gonna make me lonesome if you go," and it's not "don't go, you'll make me lonesome," or anything pleading or desperate. It's just a peaceful rumination while you're in the midst of a relationship that, you know it's going to end, and that's going to suck. It's a love song, really and truly—"I've seen love go by my door / it's never been this close before / never been so easy or so slow," he sings as it opens, or "I could stay with you forever / and never realize the time," a classically Dylan way to say "I like hanging out with you."

So you've got this pretty, breezy love song, and it's doomed from the start. He spends the entire song talking about how much he's going to miss her when she leaves him, and all of the things he's going to feel and do, all of the places he's going to imagine seeing her once she's gone. Well, shit—no wonder things didn't work out. But it's sly and funny, the way that it's framed. Post-divorce Bob Dylan was not much of a catch, really (maybe not the other versions, either, if you think about it), and there's something kind of amazing about watching someone frame his happiness in the context of the future sadness he'll feel when it's over.

I read somewhere, someone who wrote that she and so many other women she knew were fantasizing about young Bob Dylan as her dream man, and how she’d realized that this fantasy led to a lot of bad decisions and self-obsessed jerks. (I wish I could remember who wrote it!) There’s a straight boy version of that, too, of course, and I had it. When Adam Duritz sang “I wanna be Bob Dylan” in “Mr. Jones,” I felt that. I think that for guys like me (and Adam Duritz, probably, who is suddenly at risk of catching a stray here), the biggest part of growing up is realizing that the sort of romanticized narcissism Dylan so often embodied is not the same thing as his creative genius—that, in fact, they’re often two distinct things that might even work at cross-purposes—and adjusting the way we behave accordingly. (Marianne Faithfull once told a story about Dylan destroying the only written copy of an unrecorded song in front of her because she wouldn’t sleep with him! Perhaps it was a masterpiece, but we’ll never know.)

That modeling of idealized self-obsession isn’t exclusive to Dylan (although probably very often, it comes from Dylan). You could find it in Bukowski, or Kerouac, or, hell, probably Kendrick Lamar. That's something that comes around the same time as realizing that “You're Gonna Make Me Lonesome When You Go” is about a guy who is unable to function in a happy moment because he's so focused on himself that he's already planning how he’s going to mope about the breakup. And maybe it's funny, but at a certain point, you are content to let Bob Dylan be the guy who feels that, and just enjoy the song without wanting to inhabit it anymore.

Here’s Madeline Peyroux’s breezy, jazzy version of the song. I don’t think it changes any of that stuff I just wrote to hear this song in a woman’s voice, which probably says something, though I’m not sure what.