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Short of the filetype (alot of what I have I don't believe is supported by either device) Do I need to convert movies specifically for them? Or can I load them as is?

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iTunes will convert some file types for you. For those you want to convert yourself (custom resolution, bitrate, etc) I like to use Handbrake. I'm also experimenting (right this moment actually lol) with AVIDemux.

But to answer your question, I guess it depends on what the original file type is. Here is the spec sheet from Apple.

Video formats supported: H.264 video up to 720p, 30 frames per second, Main Profile level 3.1 with AAC-LC audio up to 160 Kbps, 48kHz, stereo audio in .m4v, .mp4, and .mov file formats; MPEG-4 video, up to 2.5 Mbps, 640 by 480 pixels, 30 frames per second, Simple Profile with AAC-LC audio up to 160 Kbps per channel, 48kHz, stereo audio in .m4v, .mp4, and .mov file formats; Motion JPEG (M-JPEG) up to 35 Mbps, 1280 by 720 pixels, 30 frames per second, audio in ulaw, PCM stereo audio in .avi file format

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Try an app called OPlayer. It plays just about anything, straight from a webserver or iTunes file transfer.

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Converts videos specifically for iPhone/iPod.

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There is an iphone-app called yxplayer that can play many more video formats than are supported natively by iTunes/iPod/iPhone. However, playback often judders, the UI is quite minimalistic, and it does not remember last playback position etc.

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