By the way, mentioning the White Sox made me remember who they played in the WS that year. It blows the 04 WS out of the water. 88 years for the White Sox, never for the Astros, so from 65-05, another 40 years. 128 years combined without a WS title in the 2005 World Series matchup, just in case I'm not the only nut on here obsessed with bizarre stats and records like this.
Edit to add: after posting this, it then further dawned on me that I recalled in 2005 it was a huge deal the Astros had never made it to the WS. So turns out I can answer the second part of my question myself. Astros didn't appear in the WS until 05, so 65-05 = 40 years. White Sox last won the AL pennant in 59, so another 46 years. The World Series of 2005 had a matchup of two teams that had a combined 86 years without appearing in the WS.
This decade has been really pretty damn good to a bunch of teams that haven't had success. Much as everyone clamors about the Phillies/Yankees/Cardinals/Red Sox owning the decade, we've had the Diamondbacks, Red Sox, White Sox, Angels all winning either their first WS or first in nearly a century. Astros, Rockies, Rays, Rangers, Diamondbacks all making their first WS appearance ever. Thats pretty damn good for a single decade.