=v= The thing that made "Today's Tom Sawyer" funniest to me how well-suited it was to Fry's times, thought that made it work, but rather the contrast between the ideas expressed in the song vs. the way Fry puts it to use.
=v= Rush, a band with politically conservative ideas who dedicated one of their albums to "the genius of Ayn Rand," released that song during the years when Ronald Reagan was the nominal head of their neighbor to the south. The Reagan Administration was pumping up the U.S. economy with truly massive deficit spending, but conservatives have a huge blind spot about government spending when it's for military reasons, so instead they put forth a myth that the economic boom was the result of pioneering entrepreneurs. "Today's Tom Sawyer" is basically about these enterpreneurs, so it became sort of an anthem for the whole myth.
=v= Now, if this song was supposed to inspire a new generation of Randroids to go out and be entrepreneurial, it didn't seem to work very well on Fry. He probably just riffed off the lyric that seemed to be about Space Invaders. <_Jym_>