First two are from Crusader Kings, which, as a EUII engine game has worse graphics than the EUIII and EU:R images that follow them.
In order from the top they are:
Duncan's character sheet showing how many Dukes (blue ribbons around portrait) he has as vassals.
The inbuilt bride-finder, for not all of your bride-finding needs (doesn't tell you if she is an heiress!).
I renamed the Azores 'Pimpland', the province produces Naval Goods.
The Black-Sea-hugging Rhoxolani chiefdom at it's greatest expanse during a game I was playing last year.