Is there a program or something of that sort that
lets you put the 5 people you talk to the most
just like the My Fav 5... or no? because that would be
kinda cool to have on my pearl :]

first off are you with tmobile, and secondly if you are yes there is a program my faves,except you dont get nights and weekends, if you do get the my faves something to think about.

i have my-faves and unlimited night an weekends together.

You have to manually put in the numbers for the Fav5. There is no "auto" feature on BB.

Plus, you are only allowed to change the 5 every 30 days, so your "most called people" can change too often for this type of feature to be practical.

is it a program i can just add on to my phone
like... through the DM... or do i have to get the
service?

You have to request the service through T-Mobile.