I don't know that I'd call these holy grails exactly but:
I'd been looking to add a card like this to my collection for the better part of a decade. I'd long wanted a Satchel Paige signed card but I wanted one that dated from his MLB days and ideally was signed while he was active. I finally got a 1953 postally used Paige signed Browns team issue PC.
Likewise I'd been looking for years for a good Connery signed item when this came up:
This card was a big deal for me for a very card-nerd reason: it proved definitively that the PC back cards were Exhibit issues due to the coupon on the card back: