As a devoted (read: clinically insane) automotive enthusiast, I spend most of my time on the internet perusing car-related sites and videos when I should be doing more productive things, like studying… or paying attention to literally anything else at all that isn’t car-related. But because I am afflicted with this car crazy curse, naturally I spend a significant amount of time on used car sites looking for enthusiast cars (read: unreliable and slightly one-off). And as I enjoy tickling the keys (read: blogging) every once in a while, I thought I’d turn my interest in internet window shopping into a series of posts for your enjoyment. Not that I expect you to enjoy any of this, because I totally will not be offended and cry myself to sleep if you do not.

So, without further ado, I present the first installment of the Common Gearhead’s weekly (if I have time) series: Heinously Unreliable Used Car Battle of the Week!

This week on HUUCBOTW (wow that doesn’t really roll off the tongue at all), we have a pair of European executive sedans. This class of automobile is ideal for those pesky 1-percenters that everyone’s always going on about. Big, comfortable land yachts that are as luxurious to drive as they are to be driven around in… if you’re into that sort of thing. But for us lowly, entry-level, cubicle-dwelling gearheads, they represent the biggest and best that luxury automakers had to offer about 10 years ago.

And since I’m on a budget, I’ve limited the price to $20,000 for both cars. Let’s see what our more sophisticated but less-showered neighbors from across the mighty Atlantic have to offer.

2007 Mercedes-Benz S550 4MATIC – $19,800

The Mercedes S-Class has been the pinnacle of luxury automobiles for its entire history. With each new S-Class, you can count on Mercedes to introduce several new technologies that you’ll be able to have in your new Kia in approximately 10-25 years. This is a dictator’s chariot. The closest thing you can get to a Rolls-Royce or a Bentley without looking overly douchey.

However, as well-built as Mercedes’ generally are, being a high-strung technical marvel means that this black beauty is no cheap date when it comes time to visit the mechanic. Don’t be caught off guard when you take it in to get the window switches fixed and the repair bill has more zeros than your stoner friend’s report card in high school. Also, avoid driving through wealthy zip codes, because with an old model S-Class, you’ll look like a down-on-her-luck middle-aged former trophy wife.

To find the cars.com ad for this car, click here.

2005 Maserati Quattroporte – $20,000

Italia! Molto benne! Fettuccine! Quattroporte! Words just sound better when spoken in Italian. Coincidentally, so do engines. This beautiful bella has a Ferrari-engineered V8 under the hood and she’ll swaddle your butt with Italian leather while you cruise in an interior fit for the inside of a Prada handbag. This is a car for the CFO who fancies himself a passionate man. I’m so passionate. Look at all my passion and chest hair. It’s Italian by every sense of the word. If that model from those Fiat commercials were actually a car, she wouldn’t be a dinky little 500, she would be a long, lean, and majestic Quattroporte.

Unfortunately, the Italian method of assembling automobiles seems to be as follows:

1. Put the parts you have in front of you where you think they’re supposed to go.

2. Go home early, drink Limoncello, and tell yourself that “Antonio will finish it tomorrow.”

So, unless your definition of passion includes fiery death, this may not be the executive sedan for you, Mr. Chest Hair.

To find the cars.com ad for this car, click here.

Which one would you choose?