After countless tries and messaging a fellow TAer about how they completed this challenge. I finally found out what to watch along with a response from death snakes verifying what to watch.
Solution below
Crackle: Gas Guzzler
To complete this challenge you must watch every episode of the show featuring horseless carriages, cafes, and whimsical laughter. "The show" they are referring to is Comedians in Cars Getting Coffee. The show has two seasons with a total of sixteen episodes. Ten episodes are in season one and six are in season two. Just start from S1:E1 and work your way through to S2:E6. After watching the last episode the challenge should pop.
Congratulations you unlocked Gas Guzzler.