He certainly did earn that reputation.
Teddy's rolling now most every night
Skatin' backwards at the speed of light
He's changed in a thousand little ways
He's changed yes indeed
You know he's movin' on metal yes he's
Hanging tight with the Jack of Speed
Sheena's party there's a case in point
That right wing hooey sure stunk up the joint
He's gone he walks through the old routines
But he's gone guaranteed
He may be sittin' in the kitchen, but he's
Steppin' out with the Jack of Speed
You maybe got lucky for a few good years
But there's no way back from there to here
He's a one way rider
On the shriek express
And his new best friend is at the throttle more or less
He can't hear you honey, that's alright
Pack some things and head up into the light
Don't stop, he'll be callin' out your name
But don't stop when you hear him plead
You better move now little darlin' or you'll be
Trading fours with the Jack of Speed
Skatin' backwards at the speed of light
He's changed in a thousand little ways
He's changed yes indeed
You know he's movin' on metal yes he's
Hanging tight with the Jack of Speed
Sheena's party there's a case in point
That right wing hooey sure stunk up the joint
He's gone he walks through the old routines
But he's gone guaranteed
He may be sittin' in the kitchen, but he's
Steppin' out with the Jack of Speed
You maybe got lucky for a few good years
But there's no way back from there to here
He's a one way rider
On the shriek express
And his new best friend is at the throttle more or less
He can't hear you honey, that's alright
Pack some things and head up into the light
Don't stop, he'll be callin' out your name
But don't stop when you hear him plead
You better move now little darlin' or you'll be
Trading fours with the Jack of Speed
Lyrics submitted by blackiswhite
Jack of Speed Lyrics as written by Walter Becker Donald Fagen
Lyrics © Wixen Music Publishing
Lyrics powered by LyricFind
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Like a lot of the other comments are saying, I think this mainly about voyeurism. If the song was about his girlfriend, then why would he use the word spy. If you are a spy it means you shouldn't be caught, that is kind of the whole point, and if you are a voyeur, the whole point of the pleasure you get from it, is the fact that the other people don't know you are watching them. See a bit of a connection there?
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The chorus offers a glimmer of optimism and a chance at a resolution and redemption in the future.
Captures the rollercoaster of emotions of feeling lost while loving someone who is not there for you, feeling let down and abandoned while waiting for a lover. Lost with no direction, "Now I'm up in the air with the rain in my hair, Nowhere to go, I can go anywhere"
The bridge shows signs of longing and a plea for companionship. The Lyrics express a desire for authentic connection and the importance of Loving someone just as they are. "Just in passing, I'm not asking. That you be anyone but you”
I think the song is about MDMA (rolling) which is a stimulant.
@bkabbott No, the song is about crystal methamphetamine.