There's good news and bad news. The good news is that there's a terrific free application for the Mac called Handbrake that makes the conversion of commercial DVD movies for either your iPhone or iPod a breeze. The bad news? It tends to make pretty darn big files by default, which might not be a problem if you have a shiny new 80GB iPod Video, but it definitely becomes an issue if, like me, you have a 4GB iPhone and each movie is 1-2GB in size.

Let me show you the steps involved with converting the delightful film Harry Potter and the Sorcerer's Stone (aka Harry Potter and the Philosopher's Stone, if you're in the UK) with Handbrake.

[Editorial note: I own this DVD and so while copying it onto my phone might technically violate copyright, I believe that pouring a movie onto a device I also own so that I can enjoy the movie on multiple devices is well within the intent of "fair use" laws. Nonetheless, I encourate you to please use applications like Handbrake appropriately and within the parameters of copyright law. I am most assuredly not a lawyer.]

Step one is to put the target DVD movie into your Mac. It'll automatically start up in DVD Player: watch a few seconds and then quit the program. Leave the movie in the computer, however, and start up the program and you'll see there are a zillion complicated options you can tweak:

Ignore them all and click on "Source" in the top left, then select the DVD disk itself. Now your options make a lot more sense:

Notice on the right side the slide-out drawer of presets. There are lots of options, but the three to be aware of are "iPhone", "iPod High-Rez" and "iPod Low-Rez". While we're talking about it, notice it can also create movies for your Sony Playstation Portable (PSP) if you've got one of those, and can convert movies into an optimal format for the AppleTV unit.

Anyway, I'll choose "iPhone" and press "Start" to continue. Now it's going to take a few hours on my MacBook Pro, starting with a progress bar:

About 90 minutes later, I got here:

Another ten minutes and we were "muxing" (though I have no idea what that means, truth be told):

Four minutes shy of two hours, Handbrake told me that it was done:

The result is splendid, as you can see in the [50% reduced to fit on the page here: click to see it at 1:1 size] screenshot of the movie playing on my MacBook in VLC Player:

click to see the frame capture at full size

The problem? That file, the conversion of a 2:32 movie, is a whopping 1.73GB in size. Way too big -- and at too high a resolution, frankly -- for the Apple iPhone, which has a far smaller resolution screen. The iPhone screen itself, according to Apple, is 320x240, but the Handbrake conversion is at 853x360. It's just too big (though it's splendid for watching on my MacBook Pro screen, I must say)

As an experiment, I also reencoded the movie using Handbrake in "iPod Low-Rez", which made it only 320x128 in size (e.g., tiny). The result is letterboxed, which is annoying, but still very watchable, and the iPhone lets me zoom in on the movie too:

It's better in size at 830MB, but that's still kinda big, all in all. When viewed on the iPhone itself, the smaller image is a little bit worse in appearance than the larger movie, but since I can actually use the iPhone for more than just one Harry Potter movie, the tradeoff of lower resolution to attain smaller file size is well worth it.

For comparison sake, I also converted Harry Potter and the Sorcerer's Stone using the CloneDVD Mobile commercial software I wrote about in How to put your DVDs onto your iPhone (it's Windows-based, not for the Mac) and it correctly picked 320x210 as the output resolution and the film - with indistinguishable quality versus the considerably larger Handbrake output - was only 542MB in size. My conclusion: I can use Handbrake if I need high quality output for my laptop, but for optimal compression for my iPhone, CloneDVD Mobile's the way to go. Sorry, Mac users. (actually, it works fine within Parallels too, from what I have found)

Now if I could only borrow Harry's wand, maybe I could morph my iPhone into one of the new 1TB iPhones coming out in 2014, in which case 1.73GB/movie won't be any sort of issue... :-)