Every day When I have the time, I’ll pick a brand and choose one car I think represents the pinnacle of their design - not just the looks, but technology, engine, and desirability as well. The car had to be sold new in the USA.
My first thought for this one was “oh this will be easy - 1984 Minivan”. It saved the company, and it was a great vehicle at the time. Then I realized they were branded as Dodge or Plymouth, and not as Chrysler.
My second choice was Chrysler 300 - 2004+ models look awesome, they had some spectacular engines like what came in the SRT8 model, even the regular 5.7L Hemi was cool, and the plebian V6 model looked almost as good as the big brothers. But then I realized this would be cheating - while the engines were awesome, too much of this platform was pillaged from the MB E-class, and the car just wasn’t a real Chrysler.
So, that leaves me with the original Chrysler 300 - 1955 model, with a real HEMI engine, 331 cubic inches of American fury and ingeniousness, and a beautiful design. Some people don’t like the fact that a modern car like Lexus RC is a car made out other Lexus cars - front end is GS, middle is XE20 IS Convertible and the rear is XE30 IS, but Chrysler did it over 60 years ago. They took chunks from the Imperial, New Yorker, Windsor and made the 300, which is arguably the grandpa of all muscle cars of the 60's and 70's.
Chrysler flirted with bankruptcy plenty of times before - with the current FCA management, with no one buying large sedans, with Chrysler offering one current car, one dying car and one minivan - and Jeep is the only reason why they are not bankrupt again.