I usually wait a year or so, then try again. Worked with Robert Vaughn, Kevin Michael Richardson, Earl Holliman (he even wrote a nice letter saying he didn't know what happened to my first request), John Erwin...

The most I've written to the same actor is Peter Cullen (Optimus Prime). Wrote to him 3 times in 3 years, finally got a response back on the 3rd try.

[quote="mr2lou"]That's what I'm doing I normally leave it a year and half maybe more as I'm still getting requests back from around 15months ago! So yeah I leave it year and half maybe two :-)[/quote]
Yeah it all depends on who you are sending to for e.g. i sent to Mary Costa 1.5 years ago haven't heard back she is a very good signer she normally takes 2 months max to respond so i think i'll give her another go :)

I normally try around 5 times but it really depends how much i like the celebrity or how much i really want there autograph and if i don't hear back in 1 year i normally try again :)