Shelby GT 350 (2016-2017)
The infamous Shelby GT 350 has a base price of $64,000 USD new. That's not bad for a faster model of the Mustang GT. Since depreciation has hit, you can now find these for as low as $42,000 USD used. That's not bad for an American icon.
Polaris Slingshot (2015-2019)
This odd looking car with 3 wheels made by Polaris has a base price of $21,000 USD. However, the downside is that it would be a bad daily driver, due to its non-practical size. It can be driven even with a motorcycle license. They can be found for as low as $13,000 USD.
Chrysler 300 (2005-2019)
Often mistaken by non car enthusiasts as a Rolls-Royce or a Bentley, this American Luxury car has a base price of $29,500. For a more powerful version, I would recommend the SRT-8 variant, for more power and a more sporty look. For an earlier model, prices are as low as $6,000 USD.
Fiat 124 Spider (2017-2019)
Ever wanted an Italian sports car for under $30,000 USD? Then here's the Fiat 124 Spider. Although it is more of a show but no go car, it is still fun to drive. The styling is fairly similar to the '70's Fiat 124, but more modern. Used ones can go for $23,000 USD used.
Bentley Continental Flying Spur (2005-2008)
When you add luxury plus power, you get the Bentley Flying Spur. Made by the British car company Bentley, a new one can go for over $200,000 USD. But for older ones from 2005 to 2008 can go for as little as $40,000 USD! The downside though, is that most at this price have 70k or more miles on the odometer.
Mazda MX-5 (1990-2019)
One of the most recognizable Japanese cars today, the MX-5 is one of my favorites. This lightweight 2-seater has a new base price of $25,800 USD. Though the top speed isn't the best, the acceleration makes up for it. Ones from the '90's era can be found for less than $2,500 USD.