Which is to say, not much, but why mess with success?
The Chrysler 300 was one of the coolest cars around when it launched. Its blocky styling and burly engine note made it super cool, even if some people accused it of trying to look like a cut-price Rolls-Royce Phantom. If you've seen the styling changes that Chrysler has made for the 2020 model, you'll note that although it looks more modern than the first generation, it still hasn't changed much.
Cars Evolution on Youtube noticed that too and spent some time drawing up each different iteration of the bulky luxury sedan while also highlighting some of the changes made beneath the surface.
As expected, the overall shape hasn't changed much, and neither have many of the smaller details either. Still, there was the interesting and powerful 300 SRT8, a car that we wish was never cut from the lineup. A performance-tuned Hemi V8 sounds a lot better to us than a chrome appearance package, and we'd only wish that FCA would put more love and attention into the 300. But despite the low volume in sales, it has been a consistent seller through the years, with little investment. Therefore, little risk.
Unfortunately, this is a car that was birthed at the height of the retro era. We had the Mini Cooper, the Volkswagen Beetle, and shortly before the 300, the Prowler. Yet the 300 has outlasted the Beetle and the Prowler, while the Cooper had to make major adjustments to see the future. Much like apex predators like the shark or crocodile, the Chrysler 300 continues to stand the test of time. At least, for now.
People still like retro styling - take the Dodge Challenger as a perfect example - but unless the Chrysler 300 itself is actually up to date with its modern counterparts, it won't sell. Where is the Hellcat engine, for instance? This could explain why the future of the 300 has been uncertain.