In Puerto Rico, John meets Logan Paul. They go for a drive in Logan's Ford Bronco, talk about career highs and lows, and end up at Logan's gym, where his brother, Jake Paul, is training for a fight.
John visits country singer Jelly Roll in Nashville. They go for a drive in Jelly's RAM 1500 Laramie, and John learns about Jelly's life, from being a convict to his meteoric rise to stardom.