Depends what you mean. I don't have any experience with the .tivo files that come out of TivoToGo, so I cannot help you there. But if you get your videos via, ah, some other method, then it's extremely possible. On a Windows-based PC, I convert them to MPG using TyTool, then use Videora iPod Converter to convert to .m4v and load with iTunes. Works great.