HandBrake

I apologize in advance if this is easily-found here, but I've been digging and haven't turned up anything yet...

I've recently decided to breathe some new life into my old iPod 5.5G. I tossed a new battery into it and installed a 256GB SD card kit. Now I'd like to rip my video library to this sucker. I do remember that the last firmware release for it (1.3) did a few things with the supported video formats that made things rather interesting. The 1.5Mbps H.264 maximum bitrate became a guideline rather than a rule, so you could conceivably put higher bitrate content on the iPod for better quality (although I do remember some fairly high bitrate content getting a little choppy). I swear I also read that the 640 width limit also became more of a guideline as long as you kept it under the maximum macroblock limit. As such, you could go wider than 640 pixels with widescreen content, but I also seem to remember there being a few gotchas with that process.

I've tried taking a widescreen video and getting the most resolution I can from it, but anything wider than 640 pixels refuses to transfer to the iPod, even though the video is under the macroblock limit. I've dug for articles from around that time to get more information, but I've come up largely empty. Can anyone shed some light here? Am I remembering this wrong or is there a hidden caveat that I'm not getting? Perhaps a setting in the anamorphic options?

This hardware is so old, we've pretty much given up on it - I certainly don't have one to test anymore.

... did you try anamorphic like how apple does it? 16:9 would be 640x480 custom anamorphic PAR 4:3(display might be automatic? if not put 853)... this assuming it supports anamorphic content

Yep, custom anamorphic at 640x480 works and looks correct on the iPod's screen and a TV. It seems a bit counter-intuitive as it's a widescreen movie and 640x480 is a 4:3 aspect ratio, but I suppose that's how some of the underlying bits handle anamorphic.