Week 177: “Try Your Wings” by Blossom Dearie


The first time I heard it, one of the things I liked about “Try Your Wings” was its dream-like quality. I figured it was just because of Blossom Dearie’s light, airy voice…but it turns out there’s more to this song’s dreaminess than that.

Dion McGregor, the man who wrote the lyrics, was a sleep-talker.

And I don’t mean that he’d occasionally blurt out some incomprehensible syllables in reaction to whatever he was dreaming. No. McGregor told actual stories; narrated his dreams as he dreamt them, in a normal voice at conversational volume.

Although he’d always known he talked in his sleep, McGregor didn’t know just how much he spoke until the early 1960s, when he started sharing an apartment in New York with his songwriting partner, composer Michael Barr. Like any good roommate, Barr began recording the stories, possibly hoping they would lead to artistic inspiration, but probably just because it was hilarious. Over the years, Barr recorded about 500 of McGregor’s dreams, which were eventually released as an LP called The Dream World of Dion McGregor, released in 1964. A book with full transcriptions of the bizarre stories was released soon after, with spooky illustrations by Edward Gorey.

As you might expect, listening to the recordings is an intensely odd experience. They make sense for a while, then veer off on bizarre unexpected tangents. As long as you’re not alone in a dark room, I highly recommend giving a listen sometime. Alex Behr sums up the experience accurately:

Experiencing McGregor’s dreams in real time, as if crouched next to his slumbering form, was like being cuffed to the crazy guy on the bus—exhilarating and creepy.

So whether or not McGregor drew inspiration for this particular track from any of his narrated dream recordings, I don’t know. But there are several mentions of dreams in the song, and I kind of like the idea of Michael Barr sitting in the next room with the tape recorder on, stifling laughter into his pillow as his sleeping roommate encourages someone to try their wings.

What makes this a beautiful song:

1. Blossom Dearie’s dreamy voice. She sings quietly, like she’s being careful not to wake the neighbours.

2. The guitar and piano poke their heads out between vocal lines.

3. I can’t think of another song that uses the word “hitherto”. The only thing more awesome than a sleep-talker is an articulate sleep-talker.

Recommended listening activity:

Falling asleep with a spoon in your hand.

Buy it here.