Suck a golfball through a hose?

Well emailing a large file or movie to friends and family can be hard if not impassible, no I didn't mean impossible because I have a solution.

http://files2you.com/

This is a free service from the people who created the commercial product file catalyst.

Registered Max Filesize 200.00 MB - this is a little weak but not bad.

File types - All type allowed
Multiple uploads - 5 (not sure what this means)

Support for resuming downloads
Support for download-accelerators
100kb/s
Unlimited

You can use a service like file front and upload just about any size file as well as maintain a neat little web space if you do alot of this kind of thing. There are other faster and simpler solutions if you want to share passwords with friends or family you can just simply share free online storage space.

I recommend encrypting personal files that you might share using true crypt but your family will need to have true crypt and the password to decrypt the resulting file. This method you can encrypt a whole folder and move it as a file. You can do this with zipped archives as well. 7-Zip is a great free solution for this.