Complex sentence: The Tommy Oliver Orchestra (with Donovan sometimes providing vocals) played a song and the first contestant to ring in and guess "both" the song title and the "famous face" it related to earned 10 points.
Split into simpler sentences: The Tommy Oliver Orchestra (with Donovan sometimes providing vocals) played a song. The first contestant to ring in and guess "both" the song title and the "famous face" it related to earned 10 points.