A Great Collection; but outdated for 2010.
I should note upfront, I did not play Team Fortress 2, and I had previously played "Portal: Still Alive" so I did not play it here. I have only played Half-Life 2 and Episodes 1 and 2.
I first played Half-Life 2 on the original Xbox, and at the time found it to be a quality shooter. Fast forward probably 3 more years and I played it again on the Xbox 360. My first thoughts were that the graphics, while of course better than the original Xbox version, looked quite dated, and the game play style was from an older time. As I've noted before video games are in a not insignificant part, pieces of technology, and like all technology it can suffer from being out of date. If I were to be reviewing Half-Life 2 on its own I would probably not rate it all that high because of the fact it has been well and truly out dated. It is no surprise really, the game was originally made in 2004, and while I'm sure it has undergone so kind of updating to the 2007 version that was on The Orange Box, playing this game in 2010, it still unfortunately show its age.
However, when you combine this package with Episodes 1 and 2, you have to cut it some slack. So I have. I probably would not have ever played a Half-Life 2 for the Xbox 360 on its own, the reason I bought The Orange Box was to enjoy the Episodes; and I only played the original to re-familiarise myself with the story. As it turns out, enjoying the Episodes was no trouble. Episode 1 felt a lot like a basic extension of the original, with the most noticeable enhancement being I suppose the constant presence of Alyx Vance as an AI partner. Episode 2 I felt had a noticeable graphical improvement and the gameplay here felt refresher and set up a great third installment, which I know to this day has yet to be officially announced.
I feel that to have done right by the franchise I really should have played this game years ago. It is one of those things where once you play certain video games that have reached a certain technology level, games below that level look significantly inferior. These are old games, it is as simple as that. The Orange Box is best played as one of the first games you enjoy on your new Xbox 360, and not a game you play well into your ownership. It has some very outdated gameplay mechanics, such as limited health that requires health packs to regenerate, loading screens that stop the entire game to load, and outdated visuals.
Cutting it some slack though; it is a quality game for its time and can still be enjoyed even today. It is not as timeless as some video games that I suppose rely less on technology can claim to be, this game is very deeply rooted in cutting edge technology (at least for its time) and so it suffers from the scrutiny of technology when observed as something that is old and outdated.
Is it worth playing now? If it were any other game but Half-Life you would probably say, no.