Just about every guy has said this at one point, "I should have kept that car." Unfortunately, hindsight is 20/20. Most of us don't have the room or the money to keep every vehicle we've ever purchased. And if you did, you could slide dangerously close to being a hoarder.

My first car was a 1976 Chrysler New Yorker. It was almost identical to this one, only my sweet brown Chrysler was a two-door. I wasn't very attached to that car at the time. It was just a big, old, ugly used car that leaked oil on the valve covers and guzzled gas. Fast forward to today, and a quick internet search shows similar cars for sale between $10k and $17k!   Ugh. I should have kept that pig.

Next car was a 1986 Dodge Charger that looked exactly like this. That little ride was relatively quick, with a 2.0 turbo and it was fun to drive.  I ended up hitting a patch of ice on a curve outside of Bozeman one afternoon and slid it right into the ditch at around 90 mph. Not sure how I didn't roll it. The accident totaled the suspension. No chance to keep that one.

The 1974 CJ5 Jeep was the one car I really wish I had kept. I bought it when I was around 19. I promptly took out a high-interest signature loan and dumped a bunch of money into a built V8. That beast had so much power, it would pop the front wheels off the ground when you romped it. It was a total money pit, horribly impractical for daily driving and I was in over my head. I sold it for a loss and bought a boring import sedan. Shoulda' kept it. The Jeep, not the boring import sedan.

Don't even get me started on my dad's list of "I wish I would have kept them" cars. He had some real beauties. A '65 Mustang, an Olds 442, a Chevelle, a Grand Torino and a couple other pretty sweet rides. Dang it, dad, you should have kept them.

Leave me a Comment on the car(s) you wish you would have kept.