Rich challenges John and the audience to go deep and analyze the words of a song from the 90s era. The artist and song selected is George Michael and Praying for Time from his second solo album, Listen Without Prejudice. The fools delve into his life and career, exploring his song writing abilities and rise to fame with Wham!

As George matured into a solo artist, so did his writing. Praying for Time had a socially conscious theme, calling out the human condition of greed, selfishness, and injustice. The fools discuss George Michael's background, the pressure he felt to hide his sexuality from his father and the public, until a controversial incident gave him a reason to come out. 

The conversation continues with a recognition of George Michael's quiet but generous, philanthropic activities, and his love for Christmas which now sadly represents a tragic day for his family and fans. The episode ends with Rich highlighting George Michael's incredible voice with his version of 'Where or When' from an album of covers George Michael released called, Songs from the Last Century.