I've gone through a lot of plushes and stuffed animals, ahah. When I was like 2, I had a Big Bird ("B" because I couldn't say Big Bird) and then I remember I had Puppy, a big beanie baby, at 7. And like? In college, when the marching band went on long bus rides, I would bring my Simba. ...Yikes, I can't believe I have to say "in college" as a past tense thing.
Anyway, I don't really sleep with any plushes and haven't for years, unless I have a really bad night. I have a big Umbreon plush that I curl up with when my anxiety gets really bad. I have a lot of plushes even now, really, but I just don't sleep with them necessarily. I stopped making it a regular thing when I was like 10 probably. I do hold on to my pillow, though.