No need for two cron entries, you can put it into one with:
* * * * * /bin/bash -l -c "/path/to/executable; sleep 30 ; /path/to/executable"
so in your case:
* * * * * /bin/bash -l -c "cd /srv/last_song/releases/20120308133159 && script/rails runner -e production '\''Song.insert_latest'\'' ; sleep 30 ; cd /srv/last_song/releases/20120308133159 && script/rails runner -e production '\''Song.insert_latest'\''"