Lester leaps in is a fun one. My big band played prez's solo for one of our transcriptions. Good times and a lot of fun. The only solo I didn't like was parkers mood, more because I couldn't play rather than it was bad. Rocking solo, but good lord I've got to practice more.

Well I go about transcribing a song by listening it for a few times so that I have the melody of the song in my head and the solo that guy is playing. I also generally like to have a lead sheet for the song, so I can see what the basic melody is on paper, and what key the piece is in. Then I grab the instrument that I'm going to use (Either Guitar, tenor or alto sax) and try to play the solo the other guy is playing at the same time. Start with simpler solos and move on up to harder ones. Go for a song that moves you, and keep on at it until you get the solo. Some times it can take days or even weeks, and other times you can get a solo after a couple of listens and trys. Have fun with it most of all.