Okay, thanks to you all for help! :)

Do not beat around the bush. Like Packrat said be honest :D Sometimes they will say sure but there is also that small chance they won't.

There's nothing the manager can do if the celebrity does not want to sign. It's considered bad taste (if not taboo) to send a letter to someone asking them to get an autograph for you from someone else.

[quote="zzublue"]2) I would just pretend you're writing a fanmail letter to the celeb and switch names around and stuff.[/quote]
Don't pretend anything. Always be honest and genuine in all your letters.

[quote="zzublue"]I'm going to write a letter to my favorite actress' personal manager to request her autograph, since she is known to sign rarely via her fanmail address. So, here's what I want to know:

1) Would writing a letter to a celeb's personal manager highly help getting his autograph if the celeb rarely signs via his agency?

2) What do I need to say? I know I should be polite but more specifically, how can I make a good impression that can make me seem like a true fan(and I really am!), not like a person who just wants her autograph?

Any comments will be appreciated! Thanks! :)[/quote]
1) Highly help, I don't know. But it's worth a try.
2) I would just pretend you're writing a fanmail letter to the celeb and switch names around and stuff. :/

I'm going to write a letter to my favorite actress' personal manager to request her autograph, since she is known to sign rarely via her fanmail address. So, here's what I want to know:

1) Would writing a letter to a celeb's personal manager highly help getting his autograph if the celeb rarely signs via his agency?

2) What do I need to say? I know I should be polite but more specifically, how can I make a good impression that can make me seem like a true fan(and I really am!), not like a person who just wants her autograph?

Any comments will be appreciated! Thanks! :)