If you’ve never used AppleScript, here are two iTunes AppleScript examples to get you going. First, This one tells iTunes to play the playlist named “My Favorites”:
tell application "iTunes" play playlist "My Favorites" end tell
That script starts playing a random song from that playlist. If you want to start by playing the first song of that playlist, this script will do the trick:
tell application "iTunes" play (first track of playlist "My Favorites") end tell
Lastly, this script tells iTunes to stop playing whatever it’s playing at the moment:
tell application "iTunes" stop end tell
For many more examples of how this works, see my large collection of iTunes AppleScript examples.