Season 1

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.

John meets up with drummer Travis Barker, who shows John his 1987 Buick GNX. After a drive in Travis' Mercedes Benz G-Wagon 4X42, the duo return to Travis' studio to collaborate on an original song.

In Los Angeles, John visits his former WWE rival, The Miz. They hit the road in The Miz's Tesla Model X Plaid and talk about how The Miz went from cast member on The Real World to WWE superstar.