The cast for the second season features four Tony Award winners - Annaleigh Ashford (Gina), Ben Vereen (Peter), Linda Lavin (Norma) and Priscilla Lopez (Meredith). Ashford won in 2015 for "You Can't Take It With You," Lopez in 1980 for "A Day in Hollywood/A Night in the Ukraine," Lavin in 1987 for "Broadway Bound" and Vereen in 1973 for "Pippin."
Cannoli, whose real name is Zeus, is an Old English Sheepdog.
In the season two episode "Baseball, Walkers and Wine" Drew takes Harry to a Hartford Yard Goats game. During a scene at the game someone can be heard selling peanuts. In reality the Hartford Yard Goats stopped selling peanuts in 2019 out of respect for people with peanut allergies.
Thomas Middleditch appeared on an episode of You're The Worst which Kether Donohue also starred on.