North Korea was nowhere near as tough as I thought it would be, but Cuba was a real disappointment because it's so touristy.
Iraq should be popular as Egypt as a tourist destination; it's got the Garden of Eden, the first ever city, the Hanging Gardens, yet hardly anyone visits.
On the third day (in Iran) three guys burst in while we were talking to some students. They took us back to the hotel and turned our rooms over. When they found cameras, tapes and tourist visas, they decided that we were spies.
Blog of an American (using the name "sarin"?!) in Iraq:
http://www.devo.com/mideastlog/
It probably wouldn't suprise you to hear that Cam from 99 has been to Iran and loved it. Lovely place, lovely people... horrid government.