This week, Jason and Dee set a course for smooth waters as they dive into the world of Yacht Rock pioneer Christopher Cross, exploring his 1991 Greatest Hits collection. Track by track, they unravel the stories behind the songs—from the serene escape of “Sailing” to the driving groove of “Ride Like the Wind.” They dig into Cross’s unexpected rise, the pressure of sudden fame, and the quiet drama behind an artist who became the face of a genre he never asked to invent. Along the way, they cruise through his massive pop culture impact, including “Arthur’s Theme (Best That You Can Do)”—the Oscar-winning ballad that defined an era of soft-focus romance and late-night radio. Was Christopher Cross simply soft rock… or something far more influential? And this is just the beginning. Episode One of a two-part Yacht Rock showdown!

Next week, Jason and Dee climb aboard with fellow 80s soft rock legends Air Supply and their 1983 Greatest Hits. When the final notes fade, only one will earn Final Judgment… Who truly rules the smooth seas of the 80s?

All aboard. It’s time to set sail. ⛵️