Download Handbrake.

Insert a DVD of your choice. If DVD Player opens, quit it.

Run Handbrake. Select Detected volume, as shown in Figure 1.

Figure 1. Selecting the video source in Handbrake

Click Open. Handbrake will detect all the titles on the DVD. If you’re ripping a movie, just select the longest title in the list. If you’re ripping a TV show or something with multiple episodes on one disc, then select the episode you want, as shown in Figure 2.

Figure 2. Selecting a title

In the Destination section, set File Format to MP4 file, as shown in Figure 3.

Figure 3. Selecting the proper file format

Set Codecs to MPEG-4 Video / AAC Audio, as shown in Figure 4.

Figure 4. Selecting the proper codec

For File, enter the full pathname where you want to save your movie, as shown in Figure 5.

Figure 5. Setting the output filename

In the Video section, set Quality to Average bitrate and enter 400. This can be as high as 768, but unless you squint you probably won’t see much difference. Higher bitrate = higher quality video = larger file size.

Figure 6. Setting the video quality

Optional - Under Quality, select 2-pass encoding, as shown in Figure 7. This takes twice as long to encode, but it improves the video quality and doesn’t make the file any larger.

Figure 7. Enabling 2-pass encoding

In the Audio section, for Language 1, select the audio track in your preferred language, as shown in Figure 8. Given the choice between MPEG and LPCM, choose MPEG.

Figure 8. Setting the primary language

The Sample rate is entirely up to you. Higher sample rate = higher quality audio = larger file size. The video iPod is compatible with any of the sample rates supported by Handbrake.

Figure 9. Setting the audio sample rate

For Bitrate, you can keep the default of 128, or select a rate up to 160. Higher rate = higher audio quality = larger file size.

Figure 10. Setting the audio bitrate

Click Picture Settings. In the Picture Settings dialog, decrease Width until either it reads 320. Handbrake will auto-adjust the height to match. For a full-screen movie, the height will end up at 240; for wide-screen movies, it will be lower.

Figure 11. Resizing the movie

Close the Picture Settings dialog and click Rip. Encoding time depends on the speed of your Mac, the length of the movie, and whether you selected 2-pass encoding. Handbrake will display a progress bar, as shown in Figure 12.

Figure 12. Encoding progress

When encoding is finished, quit Handbrake.

Run iTunes. Find the .mp4 file that Handbrake created and drag it into your iTunes library, or select Add to Library… from the File menu and select the encoded movie.