How come this happens when i want to download a font?

I recommend you Altysoft DVD Ripper, it so easy to rip DVD to iPod.
If it is not under copyright then it's legal. Where is the file hosted? You can usually just use your web browser. For example, everything at archive.org is legal and you just select the file you want to download and save it.
I recommend you a free software which can help you convert Rip DVD and Convert Video to your iPod.

Mac Mod Converter is the easiest to use mod video converter on Mac OS.

It called "Next DVD Ripper". It is easy to use, you only need select "iPod Move" Profile, Next DVD Ripper will convert the movie to suitable format that can be played by iPod.
Next DVD Ripper is a free DVD ripper and video converter with easy-to-use graphical interface, fast converting speed, and excellent video quality. It can rip DVD movies and convert almost all video formats including DVIX, Xv iD, MOVE, RM, RM VB, MPEG, VB, DVD, MV, and AVI to MPEG-4 movie format for iPod, PSP, PS3, iPhone, XBox360, Zune, Apple TV, Archos, iRiver PMP, Epson Player, Creative Zen, Rubi Blue, Sony Walkman, Commodore PMX, Palm TX, Game Boy, SmartDisk, Windows Mobile Smart phone, Nokia, BlackBerry, Ketti, LG, Sony-Ericssonon, Samsung mobile phone, etc.

Tod converter for mac to play on iPod, iPhone, QuickTime, iTunes, iMovie, iDVD, Apple TV, iMovie etc.

Altysoft DVD Ripper can also rip DVD to other devices and video formats, such as: iPhone, PSP, Zune, Xbox, Nokia, avi, wmv, 3gp, mov, flv and more into avi, mov, asf, wmv, mp4, 3gp and others.
Altysoft DVD Ripper is a very easy and powerful DVD ripping software, which can convert DVD to various formats.
Altysoft DVD Ripper can help copy whole DVD to your hard diver, then you can burn them to blank DVD using burning software.

With TOD Converter, it is so easy to quickly and perfectly convert tod file.

Beside above-mentioned functions, it so easy to download YouTube videos from YouTube website, just specify the URL for the video you want to download.
Yes, it's legal.
As iPod accepts only MP4 video fromat, you need to convert DVD to MP4 video on your computer, then transfer it to iPod with iTunes.
Just google a DVD to iPod converter, or you can try cucusoft iPod converter, it's a professional dvd to ipod converter that can convert DVD movie to ipod nano/touch/classic/video.