Inspired by this thread, I was thinking about supporting cast members who seem to pop up together a lot. In that thread, it was noted that Vince D’Onofrio and Vince Vaughn seem to work together quite a bit.
One example is Steve Buscemi and Shawnee Smith- she was his bar date at the beginning of Armageddon and his live-in girlfriend in The Island.
Another was the Aliens crew (Paxton, Henricksen, Goldstein)- all of them were also seen in Near Dark and a couple of other films together.
Back in the day, many of MGM’s very best sissies (Franklin Pangborn, Eric Blore, Erik Rhodes, Edward Everett Horton) appeared with each other in various combinations in supporting roles. One of the best being Top Hat, which featured three of the four.