Well I had a small pink bear that would squeek whenever you squeezed it. I believe I got it when I was a new born from a family friend.
But my favorite toy was a doll I recieved for christmas when I was around 7 or 8. It's a dark baby with a air bag sort of thing and I named her kimmy. I slept with that doll for the longest time. ( she's still on my bed )
I gave away a lot of my old stuffed toys and such. I think my oldest "toy" I still have (though they're technically pillows, but I see them as large plushies) are my digimon pillows Biyomon and Patamon. Even older than that might be my pikachu plushie I had laying around somewhere.