In a lot of ways, it's an incredible game. It got out in 2003, same year as NFS: Underground and 2 Fast 2 Furious movie came to light, ergo the highest point of the street racing hype. MC2 and Underground were the first succesful big ones to ride that tide.
In my social circles, at the end it all came down to "which one of the two translates 'dat Fast and Furious feel' better". And this question is a bit trickier than it seems at first. While Underground got that slick visuals and style, bullet proof design (advanced tuning + short but intense races), not to mention being succesful reboot of the huge NFS name, Midnight Club 2 offered much more intricate approach to, well, racing. Which lead to constant creation of different "oh, ♥♥♥♥" moments and accidents. In my opinion, a lot of them added a bit more of the Fast and Furious franchise ferocity than an endless raw of drag racing showdowns from Underground.
Basically, every race in MC2 is a checkpoint rush. A twist - it all happens in a sandbox level. So your route from point to point doesn't matter while you've hit all of them and finished first. Throughout the game, this simple concept is being fumbled with constantly, presenting you each time a race with a slightly different freedom degree - from a "there's the only straightforward route you can take to win" to "here's a bunch of checkpoints on your map, clear them all as fast as you can, using any route or technique AND in any possible order". Dence traffic and AI racers (who also pick different routes) make sure that every race has some degree of chaos, typically. In general, that's it. And you'd be surprised how much fun it can deliver.
As I see it, there are two major additional points. First, semi-scripted events. Now and then, something happens: say, a truck blocks a way right after that checkpoint. It does that every time in the same way, but what do YOU do with that is, again, up to you. Evade? Drive under it? Make a U-turn and pick a neighbour street? Whatever, just finish first. That and some smart, tight level design (shortcuts, jump ramps etc.) and AI competitors together keep game's chaotic nature fit. No matter how good you know the map and that specific route, every time there's a chance something of the above will intervene, screw everything up and make you rethink your tactics. Such things also spawn those bright, memorable moments, like a car flying just over another car while jumping from the ramp - or crashing into each other and making a huge traffic mess.
Second, game has bikes and, subsequently, bikes-only and mixed "bikes-cars" races. They present a noticeable shift in gameplay mechanics, although it's more of an intermission for the main cars-only play. Still, bikes have their moments.
Sadly, openworld brings the most of MC2's cons, too. Naturally, it's just not that good-looking with all the resource hunger of the big spaces, especially placed near Underground (which is exactly the same age but looks way better). Also, more open space needs more complicated AI, therefore it will glitch, sometimes a lot. There are other problems (e.g. different vehicles are too similar to control, some arcade flicks like two wheels riding feel unnecessary and underbaked), but they are minor compaired to visuals and AI.
Still, in my opinion Midnight Club 2 is a decent game, that brought a lot of hours of fun to me more than 10 years ago. It's core gameplay is solid even now. And while its looks have aged not nearly as well, I absolutely advise to give it a chance. Doubt not, "she's still got it".
P.S. And yes, it works with Windows 7 just fine.