nice responses guys! thanks! i got the ripken around the time that the orioles stadium was being built and cal was still playing.....so its been a while, in addition to the letter, he also included a rubber stamped auto postcard, an orioles team sticker and a team schedule.
The coolest TTM I've ever got back had to be the typed letter and 1/2 signed cards from the one and only Michael Jack Schmidt. It was in the fall of 88 and my friends and I just got into the ttm autos that year. It took about 8 months to get back but man was it ever cool. It topped all other responses that I got including Ryan, Puckett, Brett, and Cory Snyder. In a funny note the two cards I sent were a 87 topps and an 88 fleer. My buddy Jeremy later had sent the 88 fleer and an 88 donruss. He didn't sign either fleer card.
A few years ago I sent to former reliever Dyar Miller for my Mets collection (this was in the middle of the Willie Randolph being fired in Anaheim fiasco).
He sent back my two cards signed and on the back of my request letter wrote a good sized note thanking me for being a Mets fan and also how he knew both Willie and Jerry Manuel and that Willie was a good guy and will get another shot at managing one day (which may happen this off season) and that Jerry would be a good manager for the Mets (He was a little off on this prediction). To me that was very cool.
I sent Lance Alworth a card to sign for my son (my name is Lance, son's name is Lance Jr.) and he sent the card back and a signed full sized football back as well...I thought that was just awesome of him to do, I took a pic of my son with the ball and sent it to him with a thank you card...put the ball up in a case so my kid can't destroy it, he can have it when he gets old enough to know better than to play with it when he can't find another ball lol.