Asked a few times directly by email, as well as on Droid Forums, I figured, it would help to document some things on the site.

To transfer video files to the Droid, please visit this website for details

10 Steps:Transfer music files between Verizon Motorola Droid and PC | Verizon Cell Phones blog | Reviews,specs and tips & tricks.

While it is written in regards of transferring music files, the same principle applies to movie files as well.

Playback of video files is a bit different.

The build-in Media Gallery application can play video just fine, but unfortunately, it does not display movie titles or filenames.

If you have only one or two movies on your Droid, it isnt really a big issue, but if you filled it up with 2 seasons of Two and a Half Men, things are a bit different.

To be able to see titles/filenames of the files on your device, you will need to install a more featured video player application.

For the bare minimum, Video Player, by Jeff Hamilton, can be downloaded for free from the Droid Marketplace. Rather than just thumbnails, it actually shows the filename and the filesize of the video.

(note, the limitation on the screen resolution does not apply for the Motorola Droid, the Droid is perfectly capable of playback of the full-resolution video files created by DVD Catalyst)

If you want something more fancy, the (non-free) Act One video player provides a bit more control.

More info can be found here as well.

How Do You Sync Movies to Moto Droid?