I think everyone's always taking this song a bit too literally, as in the narrator practices espionage. In actuality, I think this song has content more like I'm Your Boyfriend Now. The narrator of the song is spying on this girl, but he doesn't really want to. It was something that became almost habitual, and he wants to stop.
In the first verse, he acknowledges this. For example, his "spy glasses" are probably nothing more than standard eyeglasses or sunglasses, but since that's what he wears when spying on the girl, he considers them spy glasses.
The second verse kind of continues that, but differently. The first half shows his obsession with spying on her, as he always sees her- "silhouette is smiling at me." The second half shows he doesn't want this to happen,thus "breaking the spy glass."
I'm sure there might be some rationalization for the improv ending, possibly it's whatever plan the narrator chooses to follow. And the shear random chords could represent failure of sorts. - Kfarnstein
The song has one of the best couplets in the TMBG oeuvre: "If you want to be a spy, then you must really see" (i.e., you have to see things as they really are), "and you must really see if you want to be a spy like me" (i.e., do you seriously want to end up like me, twisted with suspicion and nervous with fear?). --Nehushtan 13:19, 21 Apr 2006 (CDT)
In the two years between Apollo 18 and John Henry I had learnt to forget the abomination that was the Guitar. Then I heard Spy! How I hated this tune. Yet over time I have come to appreciate it and perhaps understand where Flans was coming from. To me it's a kind of homage to those 60s spy pastiches that were later revived under Mike Myers and there is an upbeat cheerfulness that was at odds with the grunge at the times. It is a parody song though laden with puns and cliches and cleverly constructed though the song is, it doesn't bear up to repeat listens (not to me or indeed many of the they might be wikians). It does show how versatile the band were though and how they could skip around genres. They'd earn the big bucks utilising this skill for adverts, soundtracks and kids albums and without these side projects to get the money in, I don't thing the Giants would have gone on much past 2000 so I'm glad they can do it. No, the reason I disliked Spy so much was the live version. Around 1994 the band seemed to change with far more ill advised crowd interaction (when I first saw them in 1988 they shut up and sang as many songs as they could which was perfect) that would double it's length. I think I've seen shows where they played this with The Guitar and Drink and as these lengthy "workouts" would go on I kept thinking of all the songs that they couldn't play because they'd spent so much time wasted on old style showboating. (Mr Tuck)
John Henry is All About the Same Death, But in Alternate Realities Tour
Wait, what? It hasn't been 4 months and there's already a new JH interp? That's right, Little Jimmy, it's time for another colossal reach of an interpretation. This time, it's Spy.
So this guy sees a woman spying on him. He tries to catch her in the act and fails. She kills him, and the jam part of the end is his life flashing before his eyes.