Midtown Cowboys is a sitcom where two aspiring ranchers try to hide the cow in their apartment from their landlord, Mr Featherly. In Situation: Comedy, The Director recruits Sam and Max for the main roles. Mr Featherly is played by Philo Pennyworth, who later changes his legal name to Mister Featherly to make the royalties easier to deal with.
Midtown Cowboys thrives on cheap laughs and seems to be largely a vehicle for product placement ads. Its popularity and excessive reruns lead it to be repeatedly referenced throughout Sam & Max Season One and Two. Two episodes are shot in-game, the first in Situation: Comedy and the second in Night of the Raving Dead. The trailer for What's new, Beelzebub? seems to be videotaped over the trailer for the Midtown Cowboys movie.