Jay Jurden, Calvin Leon Smith & Nick Kroll on High Maintenance (2020)

The HBO series High Maintenance recently returned for its fourth season, as The Guy (played by Ben Sinclair) continued his marijuana business, crossing paths with various individuals across New York, providing a peek into their lives. Episode 2 had him making a delivery to Matthew (played by Calvin Leon Smith) who was preparing for a paid night of sex thanks to a dating app. His date Travis (played by comedian Jay Jurden) arrived and the two ultimately made it to the bedroom with their clothes coming off. Jay showed rear nudity for the lengthy bedroom scene. Nick Kroll also appeared in the episode playing himself, working on a set alongside Rebecca Hall (also playing herself) as they worked with another of The Guy's clients, a film set intimacy coordinator. Nick appeared almost naked as his pants were lowered. There was a bit more gay content in the episode as the coordinator also helped two actors (played by Ean Castellanos & Dominique Allen Lawson) with a love scene, leading to a rehearsed kiss.

Jay Jurden

Calvin Leon Smith

Nick Kroll

Ean Castellanos & Dominique Allen Lawson