I think to just come up with a list of a couple of cigars isn't really productive. I think it all depends on the size you prefer. To me, the absolute must try cigars are Upmann Sir Winston's and RyJ Churchill's. Some people don't like cigars of that size as they take a long time to smoke. So here are some choices I would suggest in various size groups. I'll just kind of do small, medium, large and figurado.
Small cigars: Monte 4, Partagas Short, Bolivar PC and PLPC
Medium cigars: Bolivar Royal Corona, ERdM Choix Supreme, Punch Punch, Cohiba Robusto
Large cigars: Sir Winston (what else) RyJ Churchill, Trinidad Fundadore, Rafael Gonzales Coronas Extra
Figurado: Monte 2, Upmann 2, Bolivar Belicosos Finos
These are my suggestions. Some would agree, some would say WTF. It's all opinion. But if I were asked what you've GOT to try, these would by my suggestions.