Complex sentence: He attended Newton North High School and graduated in 1985 along with comedian Louis CK, with whom he would later be nominated for Outstanding Lead Actor in a Comedy Series at the Primetime Emmy Awards multiple times.
Split into simpler sentences: He attended Newton North High School and graduated in 1985. He also graduated with comedian Louis CK, with whom he would later be nominated for Outstanding Lead Actor in a Comedy Series at the Primetime Emmy Awards multiple times.