My lovely internet friend "Ray Adkins" sent me a really interesting video made by the American government in 1943 to talk up São Paulo and Brazil to Americans. It's long, but worth watching. I think my favorite part was the awkward English words they used for a lack of a good translation, like "the interior of the country" and the "rector of the university." Oh, and their nice translation of serra to "precipitous escarpment."
Also, I find it interesting that there's vurtually no mention of the military regime, just a few images that happen to say "militar" on boxes and stuff.
Check it out here (it's grandparent friendly!):
To get a more modern idea of São Paulo, I recommend Anthony Bourdain's No Reservations episode on Brazil in general and the city in specific. It's witty and thoughtful without being too naive or Americanized.
If you're too cheap for cable, like me, you can watch it here on YouTube in 5 parts, starting with part 1 here:
PS: Does anyone know how I can change the size of the YouTube videos so they don't take over my side bar? I tried to use the customize feature on youtube itself, but it doesn't cooperate.