Time to Make Puns and Change Lives! Let's Play Callahan's Crosstime Saloon!

Well first is Bela Lugosi and 9 is Vincent Price, (I just looked for their names and probable rebuses for them,) Five is… Bernard Lawton? Don’t know what the Chicago train is, so not sure. 8, Pearl Gray and 10, Crazy Ray?

…This is hard because when I try to think of synonyms for these words my brain just translates them into Swedish, which, fyi brain, isn’t helpful. Also, I want to look up some of the actors I can’t remember the names off but that’d be cheating.