Adam Sandler and David Spade got to know each other quite well while working on Saturday Night Live together. Their tenures overlapped, and the two frequently performed in sketches together. Along with Chris Farley, the trio played the three "Gap Girls" — superficial young ladies who hang out at the food court of the mall where they work, gossip, and harass other retail workers.

In 1995, the same year Sandler landed his first starring role in Billy Madison, Spade and Farley took their film careers up a notch with Tommy Boy, followed by Black Sheep. Farley's death in 1997 precluded that team-up from continuing, but Spade fell in with Sandler, who produced several of Spade's starring vehicles — Joe Dirt, The Benchwarmers, Grandma's Boy, Dickie Roberts: Former Child Star — and ultimately the pair shared screen time in both Grown Ups films, Jack and Jill, The Ridiculous 6, The Do-Over, and Sandy Wexler. Spade doesn't have a role in Hubie Halloween, but that could be because he was busy making another 2020 Sandler-produced project — he starred in The Wrong Missy.