If it seems odd to go back two generations, allow me to explain.
The Way It Was: XBox in the early 2000s
My history with the XBox starts when I lived up in Washington and worked for Microsoft. I won a contest testing employees' knowledge of EAI, and the prize was an XBox. I brought it home, along with several XBox games purchased at the Microsoft Employee Store. At the time, my girls were 6 and 4 and my son was an infant.
The games we found most compelling on the original XBox were Midtown Madness 3 and Indiana Jones and the Emperor's Tomb.
Our Favorite XBox Games
Midtown Madness became an instant family favorite. It has a lot more humor than most driving video games, and lets you drive around (or smash up) Paris or Washington DC in great detail, by yourself, with a second player, or with robot players. You can race, perform challenges, or just cruise around. It's a hoot.
Indiana Jones and the Emperor's Tomb is also great fun. Who doesn't want to be Indiana Jones? You go through a series of levels in the jungles of Ceylon, then in a castle in Prague, later to Istanbul, and finally to various parts of China. You fight, whip, explore, make discoveries, battle monsters, and have to solve puzzles. It's epic and captures the experience of being Indiana Jones very well. It took me 4 months of weekends to get through all of it, and I loved every minute of it.
Indiana Jones and the Emperor's Tomb
Aftermath: The Later Generations and No Backward Compatibility
As much as we loved our XBox, it eventually died. The logical thing to do was get an XBox 360, which is what we did. The 360 had some nice improvements, such as wireless controllers... but also one big, glaring flaw: it wouldn't run games for the original XBox! No Midtown Madness, no Indiana Jones and the Emperor's Tomb.
I was stunned. In the computer hardware industry, it's the norm to retain compatibility with earlier platforms so software applications will continue to work. Not doing so disrespects the customer's investment and doesn't give customers any incentive for brand loyalty. Microsoft certainly understands this principle well in general, but not at all in the XBox division.
There was some outcry about this, and Microsoft did institute a compatibility program where some games were updated to work on the XBox 360. But the games we loved were not included in this effort.
And so we bought some new games that worked on the XBox 360, but none that we liked as much as the original XBox games. The makers of Midtown Madness 3 did not come out with an XBox 360 version. The makers of Indiana Jones and the Emperor's Tomb had plans to come out with another Indiana Jones game title for the newer videogame platforms, but ended up scrapping those plans in favor of a Star Wars themed game.
Highly, highly disappointing. As years went by, my family continually reminded me of how they missed those original XBox games.
More recently, Microsoft announced their third generation gaming platform, XBox One. I paid much attention: would they change their tune about maintaining compatibility? No such luck: XBox 360 games do not run on the Xbox One, Microsoft had learned nothing. I decided then and there I wouldn't be getting an XBox One or any future Xbox platforms. It's bad enough to have been burned once.
Getting a Used Xbox: The Magic is Back
Recently, I had the opportunity to pick up an original first-generation Xbox -- and we love it. We're happily ripping up Paris again in Midtown Madness 3. I've been able to introduce my 11-year old son to Indiana Jones and we are now going through it together level by level.
Follow-up - 6/17/15:
It seems there's been feedback from enough people who feel like I do that Microsoft has decided to change its stance on backward compatibility. They have announced XBox 360 compatibility for the XBox One. This will only be for a select subset of titles, however, so whether your favorite 360 game makes the cut or not remains to be seen. There's nothing here for compatibility with original Xbox games.