| Background: Apple released the 5th generation iPod capable of playing videos on Oct 2005, evolving the portable music player of choice into a multimedia platform for everything from TV shows to music videos. The video iPod has a 320x240 pixel, 2.5-inch, 260,000 color display, and supports playback of H.264 and MP4.
What you will need
You can convert various video files to iPod for Windows with just one software, either Cucusoft iPod Movie/Video Converter or Cucusoft DVD to iPod Converter.
Cucusoft iPod Movie/Video Converter can convert almost all video format to MP4 or H264 which can be played on the video iPod, including AVI, MPEG, WMV, ASF, RM, RMVB, MPG, MOV, ASX, AVS, DivX, XviD.
Cucusoft iPod Video Converter + DVD to iPod Suite includes all functions of Cucusoft iPod Movie/Video Converter. Besides, It can rip DVD to iPod, AVI, MPEG, VCD, DivX directly. Recommend!!
Want to convert DVD to iPod for Windows? Guide is here.
To Mac users, try iPod video Converter for Mac
Procedure
1. Download Cucusoft iPod Video Converter + DVD to iPod Suite (Recommend!) or iPod Video Converter, install and run it.
Related download
To convert RM/RMVB real media files to iPod, Maybe need to install Realplayer
To convert WMV, ASF to iPod, Maybe need to install Windows Media Player
2. Load the video files you'd like to convert by clicking "Open file" button.
The iPod software supports many video formats, such as AVI to iPod, MPG to iPod, WMV to iPod, RM to iPod, RMVB to iPod, ASF to iPod, MPEG to iPod video...
3. Click "Output Folder" and choose the pathname where you want to save your video files. Click "Convert" to start converting video to iPod MP4 or H264 files.
Tips: Before converting, you can click 'Advance -> Video settings' to set 'Video format', 'Resolution', 'Framerate', 'Output Quality'. If you'd like to convert video to H264 .mov files, please set 'Video format' to 'H264(.MOV) FQ Variable Bitrate'. 'MPEG4(.mp4) FQ Variable Bitrate' is the default value. Certainly, you can also set 'Audio Bitrate', 'Channels', 'Sample Rate' and 'Volume' in 'Audio Settings' page.
4. After converting, you can open the output folder to check the MP4 or H264 .mov files.

5. Find the .mp4 or H264 .mov file that iPod converter created and drag it into your iTunes library, or select "Add to Library" from the "File" menu and select the encoded movies. Now, you can watch the movies with iTunes or Quicktime Player. Then, you can load the MP4 or H264 files to your video iPod by clicking "File -> Update iPod".
Tips: Download iTunes+quicktime Player from here.

Guide - How to convert DVD to iPod video?
If use the trial version of Cucusoft iPod Video Converter + DVD to iPod suite, a watermark will be displayed on the iPod video converted. To remove the watermark, please get the full version here.
If use the trial version of Cucusoft iPod Movie/Video Converter, a watermark will be displayed on the iPod video converted. To remove the watermark, please get the full version here.
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Cucusoft DVD Ripper - Convert DVD to MPEG4, AVI, DivX
Cucusoft MPEG to DVD Burner - Convert MPEG to DVD, MPG to DVD
AVI to DVD/VCD/SVCD/MPEG converter - Convert MPEG/AVI/RMVB/MOV/XviD to DVD
iPod Movie Converter for Mac - MOV, DivX, XviD, MP3, AAC, DVD, Vob, MPEG, AVI, WMV to iPod on Mac.
iPod Video Converter for Windows - Convert AVI, DivX, WMV, ASF, RM, RMVB, XviD, MOV to iPod Video files.
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