Oh hey Reader,

This is the first email in a new series I'm trying, that doesn't have a name (yet). Each week you'll receive two emails, both centered around a single marketing or copywriting concept. This one is about Bob Dylan.

It’s January 25, 1985 (also known as The Greatest Night in Pop) and Bob Dylan is choking.

Through a feat of pre-smartphone logistics involving a suitcase full of Rolodexes, FedExed cassette tapes, and Lionel Richie being friends with *literally everyone*, 40 of the decade’s biggest pop stars have gathered IN PERSON to record We Are the World, a charity single to raise money and awareness for African famine relief.

All night long, everyone is doing the most. Producer Quincy Jones is herding cats and checking egos. Cyndi Lauper practically blows the ceiling off. Bruce Springsteen sounds like he’s been gargling broken glass.

There are no managers, no assistants, no glam squads—just a bunch of shit-hot artists trying to hold their own with a bunch of other shit-hot artists.

And Bob Dylan probably belongs in that room more than anyone else. Out of all these stars, he was known as “the concerned musician.” Singing for a cause was his whole THING.

Springsteen is fanboying and in awe. Sheila E. is so intimidated she just says “HI,” and scurries away.

The producers. The engineers. The photographers. Everyone sees Dylan as a “legendary, iconic symbol—to Americans and the world,” and they are so psyched to have him on this project.

It’s like his presence legitimizes the whole thing.

No pressure, right? 🤷🏻‍♀️

Here’s the thing though: The mid-80s were not such a great time in Bob Dylan’s career. After being a revolutionary folk singer—the Kurt Cobain of the 60s and 70s if you will? I will happily discuss/fight about this with you—he went through what most creative entrepreneurs would recognize as a “dip.”

All told, Bobby D. was having a crisis of confidence.

Surrounded by these huge voices, singing their hearts out on an anthemic, imploring chorus, he looks like James Caan mouthing the words to “Santa Claus is Coming to Town” at the end of Elf.

Oh, buddy. 🥹

Finally, it’s time for the last two solos of the night—Springsteen and Dylan doing that “refrain behind the refrain” at the end of the song.

Bob Dylan steps up to record his solo, and he is so uncomfortable. His curls are frizzy. He mumbles the lyrics like your 10–year-old nephew, inaudible and unsure, and visibly lost.

He keeps trying to sing like the other singers on the track, but Bob Dylan doesn’t sing like that, and he just isn’t sure what to do.

Ohhh, BUDDY.

Quincy tries to help. He says, “It was great before, when you were just singing it over the chorus!”

Basically, he’s telling Bob Dylan to JUST BE Bob Dylan, but Bob Dylan can’t see that that’s what they WANT, and it doesn’t occur to anyone else that Bob Dylan, the FOOKIN LEGEND, doesn’t get this, so nobody is saying the right thing.

Then Bob says:

A small group gathers around the piano, where Stevie Wonder plays the chords over and over again.

And then you hear, clear as a bell, Bob Dylan singing the lines in the way only Bob Dylan can sing them: There’s a choice we’re makin’ We’re savin’ our own lives It’s true we make a brighter day For you and me Except… plot twist! It’s NOT Bob Dylan singing:

Except… plot twist! It’s NOT Bob Dylan singing.

It’s Stevie Wonder, doing a spot-on impression of Bob Dylan. Showing him how it would sound if Bob Dylan was being THE MOST Bob Dylan.

And for the first time all night, Bobby smiles. The relief is palpable.

Then he laughs, and keeps laughing. I’m pretty sure he gives Stevie Wonder a hug.

Oh yeah—THAT’S what I sound like. I’m Bob Fucking Dylan!

I don’t know what kind of person Bob Dylan is or isn’t. I don’t know what he’s like to work with; I don’t even love his music, most of the time.

But I can see when someone is deeply outside their comfort zone, and what a brave thing it was for him to show up to this bizarre event, and how intimidated he was—even though everyone else there was intimidated by HIM—and how he stuck it out til the very end, anyway.

When he finally crushes his solo in that nasal, arrhythmic, slightly off-key, half-spoken-word style that is so quintessentially Bob Dylan, you hear a giant WHOOP! coming from the other room. People rush in and clap him on the back. Quincy is relieved AF.

And I’m on the couch, dabbing at my eyes, because this right here is what I do for my copywriting clients.

You’re Bob Dylan—brilliant and talented and sometimes misunderstood, and your voice doesn’t sound like any of these other ones, no matter how loud or great or famous they are.

And I’m Stevie Wonder—I know what your true voice sounds like. I can sing just like you sing, and in doing so remind you why you’re so fucking awesome.

It is really hard to hold your own greatness. It’s not something we’re conditioned to be comfortable with, and it’s even harder when your career is in a weird place and your confidence has gone to shit.

Being even more yourself is often the last thing that would occur to most of us—and even if it did, there’s so much noise out here that it’s hard to remember what your real voice sounds like in the first place.

That’s why people work with me—I can hear your voice in its clearest, weirdest, YOU-est, even when you’re not sure you remember what it sounds like.

There’s a reason all those stars in 1985 were falling all over themselves about Bob Dylan, even though at that exact minute he was probably feeling the least “Bob Dylan” ever. . .

. . .THEY could see his impact and influence on their own careers, stretching through the decades. They didn’t give a shit whether his 80s albums were well received or not.

They weren’t inside his head. All they could see was the legend in their midst:

And. . . 👻 BOO! 👻

That’s what I see right now, peering into this screen and reading these words.

What’s up, you fucking legend?

All the quotes in this piece come from The Greatest Night in Pop documentary, unless otherwise noted.