"Mid-life Crisis" Car Purchase

[Jrussblues]

I wouldn't say that I am actually having a mid-life crisis. I turned 50 in January and as some of you may already know from a couple of my other threads I'm about to be single again. I have been wanting a new car for a while now and since I will have no one else to please but myself I'm thinking about getting something more fun and interesting. With the exception of a '69 Dodge Charger that my parents bought me in the mid 80's, I have had nothing but inexpensive and practical cars my whole life. My current car is a 2007 Chrysler PT Cruiser. I got it because it was cheap and had plenty of room in the back to haul gear. Prior to that I had a Hyundai Elantra and before that a Dodge Caravan. Yawn!
Now I'm looking at modern muscle cars and since I'm a Mopar guy I'm leaning toward either a newer Challenger or Charger. The Charger is a bit more practical since it is a four door sedan but I really like the look of the Challenger. I'm going to check out the Camaro and Mustang as well. Whatever I get it will be used, probably in the range between 2012-2015 and I would like to stay in the low $20K range as my max price.
Curious who else has made a less practical car purchase and did you later regret it?
What are some other models I may want to check out?

Okay, something I actually know about.
My wife has a 2015 base challenger we bought new in feb of 2016 for 22500 which was 6k off of the sticker at the time.
1. I wanted the rt hemi, we drove it, it was awesome, but she found the large screen to be distracting and it wasn't going to be my car so I told her to get whatever she wanted . I was sad because it was 10k off of the sticker on the rt and it was loaded for like 31k.
2. On the plus side, the 3.6 6 cyl hauls a** but this is specific to 2015 and up. In 2015 they overhauled the interior and some of the exterior and put in a 8 speed auto trans. So while it's not a v8 it most definitely gets out of its own way. Additionally it gets 30 plus mpg on the hwy. So it's a trade off. Also, the 3.6 is still a 300 hp motor and if you dare you can add a mild supercharger to it down the line to produce 450 hp. I just did this in a couple of jeeps that use the same motor at the shop. Anyway...
3. Don't bother looking at anything before a 15' and I'm sure you can find one in the 20 k range.
4. The chargers are slightly faster than the challengers because they are actually smaller.
5. I have hauled a 6 space rack, pedaltrain in hard case, 2 basses and a smaller 115 in it plus my wife and I comfortably to a gig. Though the rear seat is a little more awkward to access in a coupe. Anyway, that's how much actual room there is in a challenger.
She has been very pleased with the car, she has wanted a challenger since they came out and after we got married last year and her Altima started to show it's age I was able to talk her into getting her dream car. It's pretty comfortable to ride in too, not like I thought a sporty car would be.