So, after some thought, and a little IMDb research for Tim and Janeane, I have found that you can make all these connections with really short chains. In fact, only one needed more than one actor in between. Here we go:
John Belushi was in The Blues Brothers with Paul Reubens (seriously, Pee Wee Herman was their wine steward at the fancy restaurant), and Paul Reubens was in Mystery Men with Ben Stiller.
Pauly Shore was in In the Army Now with Lori Petty, who was in Tank Girl with Naomi Watts (I love that movie).
Lucy Liu was in Charlie’s Angels with Drew Barrymore, who was in Whip It with Juliette Lewis, who was in Natural Born Killers with Woody Harrelson.
Tim Curry made a guest appearance on Criminal Minds which features the wonderful Kristen Vangsness, who is so good they put her in the new Criminal Minds; Suspect Behavior with Janeane Garofolo.
After BaseballChica’s revelation that the mean connection for people in Hollywood is four people, I can’t decide if I want to challenge myself to make all chains from now on in four people or fewer, or to find pairs that are waaaay far apart.