PureDoxyk is right about the
blue jeans, but wrong about the
anime.
Videotapes (And CD) in
Japan are
insanely expensive; I found that the equivalent of $70 was not at all unreasonable for two episodes of anime. So this probably wouldn't work.
Laserdiscs are cheaper, sometimes, but the US market for them just went from small to nonexistant.
Another lucrative way to visit Japan is to teach English. Not as risky, and it does work.