John Mulaney, a stand-up comic searching for his big break, experiences drastic life changes when narcissistic comedy legend and game-show host Lou Cannon hires him as a writer. While the job is everything John was searching for, Lou proves to be a nightmare to work for. John must handle the stress of his new job and the guilt he feels over not being able to be there for his best friends and roommates, a tightly wound personal trainer named Jane, and Motif, a powerhouse comic. Rounding out the people in John's life are Andre, a trust-fund baby who seems to show up at the worst possible moments, and his neighbor Oscar, who often serves as an oracle of sound advice.