Exterior Looks
The Chrysler 300, unusual for cars of this type, looks very good. I love the aggressive yet restrained look of the grille/headlights combo, and the intimidating stance. It looks very gangster-esque. I imagine Al Capone would drive this if he were to stalk the streets of Chicago today. It compels you to drive it with just your left hand on the top of the wheel. The Cadillac Escalade does the same.

Interior Looks/Functionality
I will start this section of by saying the 300's interior does not stack up to some of it's German rivals. However, it is cheaper, with a starting MSRP of around $30,000. It doesn't have quite the same quality or gadgets as it's competitors. However, for the money, you do get a fairly nice place to be. The plastics are a bit scratchy, but I love the seats, and the 8.4-inch touchscreen system works surprisingly well. It took a few minutes to get familiarized with the system, but is very easy and simple to use. It is also the first car I've been in with an analogue clock. I thought it would look a bit cheesy and overdone, but it looks nice. However, the headlights are very strange, as the high-beams would only come on if you held the little lever down. Another minor issue would be the gear selector. It is too sensitive, and the space in between the P,R,N and D are so small you almost always end up going to far or too little. The interior could also do with a sat-nav, which is an optional extra.

Comfort
For a big car like this, you kind of expect a lazy, sloppy ride. But with the Chrysler, you don't get it. It was fairly comfortable, the driving position is good, and the rear seats have adequate leg room. The ride is a bit bouncier than say a Mercedes C-Class, but for the price this is a comfortable car. I did note that the ride in the back is a bit jigglier than in the front.
Driving Dynamics
This isn't a sports car. Nor is this base version a muscle car. The steering is a bit vague, and the front wheels are a tad disconnected. But as far as the engine goes, perfect. It offers adequate power with minimal fuss. The steering may not be as good as say a BMW, but again, you have to consider price.
Who is this car for?
I have just introduced this little section, which describes what kind of person I think fits this car best. The Chrysler is tough. I'm tempted to say it's good for a middle-aged dad who likes to ferry his kids around in an big, tough, muscle car. But the 300 is more than that. I think it works for two people. The aforementioned cool dad, and I think a retired person who loves big, luxurious American cars with looks and a good engine.
Update
Over the course of the trip, I have learned more about certain aspects of the 300. For instance, the gear selector is really an issue, it is far too sensitive, you almost always end up going past the gear you are looking for. Second, it makes a very irritating noise when you reverse, like a ghost howling. Finally, I have noticed something about the interior plastics. In the passenger seat, where my knee hits the center console, the black plastics have started to wear and become gray-ish. Further investigation reveals that if you so much as scrape your knuckle against the plastic, it leaves a white streak on the plastic. This may be fixed by simply wiping down the plastic, but I'm not so sure. This could leave the car looking very worn very quickly, considering this particular 300 only has 13,500 miles on the clock.
Conclusion
When I first got in the Chrysler, I didn't think I'd like it. I usually like little European cars with complicated interiors and great handling. But the 300 surprised me. I love it's looks, presence, touchscreen system and the general feeling that you are in a big, intimidating car. This isn't even the full-bore V8 300S, but even so, it's a great car.