Sky Sailing is a side project of Adam Young, the artist behind Owl City, Po… Read Full Bio ↴Sky Sailing is a side project of Adam Young, the artist behind Owl City, Port Blue, Color Therapy, Insect Airport, and Seagull Orchestra. The songs on the album, An Airplane Carried Me To Bed, were written before he started Owl City.

The debut album An Airplane Carried Me To Bed is a step into the past, the documented account of a shy boy from Minnesota with more hopes and dreams than he knew what to do with. When you listen to this record, you can hear naivety, innocence, inexperience and the wide-eyed imaginings of a wishful thinker.
It is both light and dark, optimistic and melancholy. Unpolished and dusty, it is an antique and therefore holds a truly unique and graceful aesthetic within. Though there has always been just one artist behind the music....before there was Owl City there was Sky Sailing.

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Captains Of The Sky
Sky Sailing Lyrics

Jump to: Overall Meaning ↴ Line by Line Meaning ↴

Mid air
I woke up beneath the flight deck
On the wall paper airplane
As you stare
I strap my helmet on and left your driveway behind

[Chorus]
Flutter all through the night

And we can blow the clouds around
This paper hanger skyline
Summer smile again
And you can disappear
But I'd rather be here

Dive bomb
We descended down the stair case
And crashed to the kitchen floor
So long
Our flight of downy dreams
Preened our soft paper wings

[Chorus]

Hello down there
The morning made of singers
In the air
Keeping the midnight stars
Held high
We are captains of the sky
Waving goodbye

Hello down there
The morning made of singers
In the air
Keeping the midnight stars
Held high

We are captains of the sky
Waving goodbye

Overall Meaning

The song 'Captains of the Sky' by Sky Sailing is a beautiful and whimsical representation of a dream-like state of being, where the singer finds himself waking up mid-air, beneath the flight deck. He appears to be lying on a wallpaper airplane, staring out into the unfamiliar yet enchanting landscape that stretches for miles around. As the woman stares, he straps his helmet on, ready to leave her driveway behind. The chorus invites the listener to flutter all through the night, allowing the paper hanger skyline to swirl around like clouds. The singer revels in the beauty of it all, while acknowledging that he'd rather be here than be anywhere else. The second verse sees the singer diving down the staircase, crashing to the kitchen floor, and taking his magical flight of downy dreams, preening his soft paper wings. Again, the chorus is repeated, except this time with the added depth and dimensionality of the morning, made up of singers, keeping the midnight stars held high. Finally, the singer is bidding adieu to the world down below, acknowledging that he and his ethereal company are indeed captains of the sky.

Line by Line Meaning

Mid air
I found myself in the middle of the sky

I woke up beneath the flight deck
I woke up under the part of the airplane where the captain sits

On the wall paper airplane
I was on a paper airplane, as if I were in a dream

As you stare
As you look at me

I strap my helmet on and left your driveway behind
I'm ready to take off on my own adventure, leaving everything behind

Flutter all through the night
Flying through the night with a carefree feeling

And we can blow the clouds around
We have the power to move the clouds with our plane

This paper hanger skyline
The world we are flying in feels like it's made of paper or as if it were not real

Summer smile again
Feeling happy and carefree like in summer time

And you can disappear
You can leave and go on your own adventure too

But I'd rather be here
I prefer to stay flying here in the sky