I've been kicking around the idea of setting up a central media server for delivering content to various devices on my home network, and one of the primary functions would be the streaming of iTunes content directly to my TV. If this could work it would be ideal for my situation, but the various options I was finding for serving up media wasn't really impressing me. One particular option that looked promising was XBMC, but some of the other routes I pursued using Windows Media Player or just Windows in general was taking me far from the direction I wanted to go.
I own an Xbox360 so I started looking into that as a media extender and found that while it does support streaming content from a PC, that PC must be running Vista, Windows 7, or Windows Media Center, none of which do I own nor am interested in using. In addition, even if I did go that route, I couldn't find much concrete info on being able to stream .m4v files through Windows Media Player or the Zune software to the 360 and that is key for me (I am aware that generally you can rename .m4v files to .mp4 and then it works fine but I'm not interested in jacking with my library just to stream content to my TV).
So then I stumbled upon Connect360 by Nullriver Software, which in short, provides the ability for your Mac to share out your iTunes library (and iPhoto) with your Xbox360. Simple as that. The application costs $20 but has a free trial download for you to ensure that it will even meet your needs. It did mine. Connect360 is a very quick install which adds an additional pane to your System Preferences and an optionally additional icon to your menu bar. You can select which content areas to share out and limit access to devices on your network as well. Of course, the Mac and the 360 must already be on the same network. Once installed, turn on the sharing, then on your 360 go to your Music LIbrary, Photo Library, or Video Library, and you should see your Mac in the list. Select your mac to see your relevant content listed ready for viewing. The Music library has artists and genres and playlists, the Picture Library pulls in your iPhoto folders, and the Video Library lists all your video content for streaming (Tip: There's an option to filter out all video and audio podcasts if they are crowding your lists). In the trial version, it will only pick up one video, and a limited number of songs and photos. Luckily for me this was plenty. The one video it picked was an .m4v file which was again my primary concern. After an automatic prompting by the 360 to download the free plugin needed to play the special content, it played just fine, as did the music library, and the slideshow of the pictures library. I was even able to multitask the streaming by listening to my Eve Online soundtrack in my Music Library while watching a slideshow of my latest Eve screenshots in the Picture Library. Now that's just awesome.
I've already purchased a license for the application which is a painless process and so worth it IMO as opposed to the alternatives. It will definitely play a part in any future file sharing or media delivery I implement, and I highly recommend it to anyone who enjoys both a Mac and an Xbox360.
I'm Matt Hill, a Sacramento area application developer working with CF for close to a decade, and this is my personal blog. 
Mar 17, 2010 at 12:52 AM Connect360 is alright but it won't play all formats like MKV and HD. Also it seems to have finished, it hasn't been updated for 64bit. Vuze has an inbuilt media streamer/server and it's free. I went back to using Windows 7 as my streaming server (with the new divx codec), which was the best, until the trial ran out.
Mar 17, 2010 at 4:20 AM I'm kinda "meh" on Connect360 as well. It works... but the performance seems spotty at times. I've got an older PC I use just for SQL Server. On a whim I tried TVersity on it, and the performance seems to be better and it plays more formats.
Mar 17, 2010 at 8:52 AM @MrBuzzy: I don't have an HDTV yet and I'm not familiar with MKV so for me those aren't a concern. Though, I think I read some documentation about it not being able to serve up protected itunes content like what you'd buy from the iTunes store. I don't do that, so also not a concern, but worth noting for anyone else. Regarding Windows 7, I did read about the built-in media server software and that seems to work with the 360 out of the box, but I only have one Windows machine and its on its way out.
@Raymond Camden: I haven't had any performance issues (in the ya know 4 hours I've been running it) but if I encounter any, I'll post them here for anyone as a balanced followup.
Apr 14, 2010 at 6:21 PM I like it. The non 64 bit part sucks, but it was a pain free and inexpensive way for me to get my media files onto my HDTV using the equipment I already have.
Fresh of BT XViD encoded AVIs play without a hitch. As a matter of fact, the only reason I landed here was because I was trying to find a mention of a 64 bit version. This is the only real site that even mentions it.
Because it runs in the system preferences, and it's only 32 bit, it seems to make me want to relaunch the whole sys preferences panel whenever I run it. Not a game killer, but before this it was pretty set and forget....