Need a "fancy" car model

Try a Packard. There are pictures and data on this page for 1950 models.

http://packardinfo.com/xoops/html/modules/modelinfo/index.php?mode=year&id=1950&ButtonYear=Go

Don't overlook GM's prestige model, the Cadillac, that was enormously popular in the post-WWII South.

*Ever heard of "fifth wheel" driving? Check out what was available for one's Cadillac in '50-'51... Here's the actual TV commercial...

http://www.youtube.com/watch?v=NSvQVaqIyOk

Given your setup, I might also suggest something like a big 1951 Chrysler. Maybe a convertible.

Like this: http://www.remarkablecars.com/main/chrysler/1951-chrysler.html

The nightclub would suggest some who was not from dullsville. The Caddy was, and still is, a corporate exec type car. The CHrysller was more of something for an insurance salesman. Hipsters would lean toward Buicks, Packards, and other cars with ig engines. If he was involved with Mafia types, then he might have had a Caddy. He he was not as wealthy as, then there were Chevy models that were almost as good as the Buicks, and there were some neat Pontiac models.

WHat kind of image do you want to create?

Playboy...if he is really hip, he might have a British convertable car like the Triumph, MG, or Jaguar.

Thothgaurd gave the other possibility. He might have had a sports car, but I think that the Packard would be at the top of the list. If he had a British sports car, then MG would be most likely. If he was cheap, then he might have had a Mercury, which was pretty hot.