Complex sentence: He attended college at Washington and Lee University, where he majored in Journalism, and attended several school plays, after graduating college, he entered the Army, where he spent the next five years, leaving with the rank of Captain.
Split into simpler sentences: He attended college at Washington and Lee University, where he majored in Journalism, and attended several school plays. After graduating college, he entered the Army, where he spent the next five years, leaving with the rank of Captain.