I’ve been driving since 2005 and in October, 2017, I purchased my tenth vehicle. In those 13 years of motoring, I very nearly averaged a different car a year, but here’s the truth: some cars only lasted three months while others lasted seven years. Some were crashed and totaled – a consequence of my naive and exuberant youth. Others were sold, either due to boredom or necessity.

Looking at the list, there’s a clear pattern in my affinity: cumbersome, utilitarian four-wheel-drive “tractors” masquerading as passenger cars. I’ve owned five Subaru station wagons and three Jeep Cherokee XJs. The other two – the literal black sheep of the fleet – easily rank highest on the quintessential gearhead score card, but I never really mixed well with those types.

In ranking my past, I’m going to do so on two levels: subjectively, i.e. my personal favoritism, and  objectively, i.e. which cars were/are actually good. One was pretty easy to determine – the other not so much. What makes a good car anyways? Is it reliability? Value? Utility? Flexibility? Efficiency? Performance? Prestige? Aesthetics? The way I see it, looking at these cars objectively requires placing yourself in the minds and number crunching hearts of a Consumer Reports vehicle tester. Who’s your audience? The average consumer of course.

Obviously, subjectivity is more entertaining than an objective analysis, so without further adieu, here is the definitive, subjective ranking of the 10 cars I’ve owned – with a little objectivity thrown in for good measure.

10: 1996 Subaru Legacy L Wagon 2.2 AWD stick

Objective Ranking: 3

This was the second car I owned. It was purchased with 146k miles in 2006 right when I was entering college, for, I want to say, $4500 at a Subaru dealership. I called it Whitey with the intent of keeping it to the point where it would routinely break down, prompting me to be able to proclaim “Whitey keeps bringing me down.” (That’s truly genuine by the way). I liked it because it was my first, personal stick shift car, it was all-wheel-drive, it was a Subaru, and it was a station wagon. I took it to the Tail of the Dragon quite a bit, and was very sloppy and slow.

Overall, the car was remarkably reliable and care free in the nearly two years that I owned it. A bit bare bones, slow and numb to drive though, this is the car I routinely forget I had… except when I remember how I lost it. Here’s a tip for all you horny teenagers with cars – girls are much less impressed by Rockford turns when they end up with the car being totaled by a pole.

9: 2002 Subaru Legacy Outback 3.0 AWD automatic

Objective ranking: 10

This car was a selective lemon. Whenever I drove it, it overheated. When it was used for an extended period by both my mother and my roommate, it drove immaculately. I seriously think it hated me. When I sold it, I found out a year later it “blew up” on the person I sold it to. When it wasn’t overheating though, it was actually kind of nice. It’s responsible for the fastest time I have ever driven from Miami to Knoxville, Tennessee – 11 hours. The car even held the “max speed” record in my GPS – 111 mph. It was the first car I ever “buried” a speedometer on too – something past 120 mph. I got a speeding ticket for doing 92 in a 65 mph zone somewhere on Interstate 26 in South Carolina.

It was probably best I sold it.

8: 1999 Subaru Legacy Outback 2.5 AWD stick

Objective ranking: 6

I feel bad for what I did to this car. Thinking about it as if it were a girl, I basically used it as a rebound following the break up of a nearly five-year relationship. For what it was, it was really neat – a super well maintained classic Subaru wagon with a strong engine, slick drivetrain, and no rust. Really. None. It was a bit ugly though, I have to admit. It looked as if it had been painted for $5, the hood wasn’t original, and after further inspection, I’m almost positive it had been in a slightly more than minor front end accident. My girlfriend also didn’t like it and if I’m being honest, it was rather temperamental. I kept my engine scanner in the glove box to clear the various knock and O2 sensor codes, fought with it tooth and nail to relocated the knock sensor, and fought with it tooth and nail to install an exhaust header. After thinking I stripped an exhaust bolt thread, I found a helicoil where I was going to install a helicoil. I guess that wasn’t this car’s first barroom brawl.

7: 1986 BMW 535i 3.5 RWD stick

Objective ranking: 9

Ugh. I had this car for five months, it was one the road for four, and in that time, I got pulled over five times. It’s the first time I ever had my car searched. It was also the first time I ever thought I was going to get arrested after shifting into fourth gear – right foot flat to the floor – in a highly trafficked 35 mph zone. I later wrote a profile piece on the car for a college journalism assignment after finding out through a background check it had nine previous owners and an odometer that traveled back in time. On the driver side, the car was riddled with dents that had to have come from a baseball bat. It was truly self aware and murderous. I’m glad I sold it.

6: 2000 Honda Civic DX 1.6 FWD stick

Objective ranking: 2

This is the perfect car for today. People from the ages of 15 to 21 should be forced to drive this car: their sister’s 18-year-old Honda Civic DX, with manual windows, no central locking, a manual transmission and no tachometer, no rear doors (two door cars really are an inconvenience), less than 100 horsepower, and little tires all wrapped up in a less than 3,000 pound package that sits on one of the best front wheel drive chassis ever made. This is a fantastic learning tool for people to drive in the real world. Instead, we shower impressionable minds with safety blankets in the form of “safety-focused” driver aides. The higher we climb up the SAE Level of Autonomy latter, the further out of reach reality becomes. Driving is a privilege the deserves the same respect a firearm is due. This car forces you to give that respect, all in an easy-to-drive, fun-to-drive, 40 mile per gallon, bullet proof package.

As good as the car is, I’m not a teenager – I’m someone who has paid their driving dues and lives in upstate New York with a girlfriend with refined tastes. The Civic therefore had to go in favor of an all wheel drive “LL Bean” catalog on wheels.

5: 1997 Subaru Legacy Outback 2.2/2.5 AWD stick

Objective ranking: 8

This car. That’s the best way to sum up a nearly seven year relationship with a true Frankenstein. This car was self aware. My favorite memory was when it wouldn’t start while I was running errands with my dad. My dad, being who he is, got mad – adamant that it wouldn’t start – and walked away to eventually get home, get his truck, and come rescue the apparently dead car. A few moments later – while a few yards away – the car started as if out of spite. I owe this car so much. It got me through college and my first big move 1,000 miles away from home. It was the first car I swapped an engine into. My first time with a suspension swap. I beat the living hell out of this car and it never wanted to die.

Eventually, it got to the point of seriously diminishing returns. It was rusted and seriously questionable. So, I did the only honorable thing I could do, and parted it out. The engine – albeit the car’s third one – went into another Outback. The transmission and radiator went into a Forester. The suspension went to an Impreza. The exhaust, driveshaft, alternator and A/C compressor are still in my parent’s crawl space. The shell was sold to a wrecking yard which sold it again to another wrecking yard. I unknowingly stumbled upon it, really stripped apart and welded to some old steel wheels, one last time before it was crushed.

4: 1999 Jeep Cherokee Sport 4.0 4X4 stick

Objective ranking: 7

This was my first serious off-road project. I bought this as a stock Jeep in a crowded, gated lot near Homestead, Florida. The first time I drove it on the road as my own, I asked myself aloud, “did I just buy a lemon!?!” That question never really went away in the nearly five years I owned it. It went through three sets of axles and gear ratios(if you include the originals), a variety of differential configurations, including the much desired “locked/locked”, and seven different sets of tires across three different tire sizes. It was constantly morphing out of sheer curiosity. I wish I would have just picked a “phase” and left it alone, but I couldn’t, so I sold it. It was a frayed relationship and I didn’t want to spend the money to get it to the point of calling it finished.

I hope to own it again and get real serious with it as a trail rig spec’d to Ultimate Adventure qualifications. (Spoiler alert: this is happening!)

3: 1998 Jeep Cherokee Classic 4.0 4X4 automatic

Objective ranking: 4

This will always be the car I want back the most, because it was the first one I owned. At the time, I loved it. The first night I had it, I couldn’t sleep I was so excited. I only had it for five months, and I was 17, so I’m not sure how accurate my memories are, but I do remember it being a delight to drive. It was pretty cherry too – low mileage, dealer trade-in. This was back in 2005, so it really wasn’t that old. It fit right in at the time – it was a legitimately cool car to have in high school. I even took it offroad, got stuck, and went places that were really impressive to get a stock Cherokee through.

The day I wrecked it was one of the worst days of my life. It was only three days before Christmas, I was driving to see a girl I liked, and got t-boned by, at the time, the literal antithesis of my favorite vehicle – a Toyota Tundra. The Jeep was totaled. My heart was broken.

2: 2005 Subaru Legacy Outback 3.0 AWD automatic

Objective ranking: 1

Ah, good olé Planet Express Ship – the “objective best” on this list and my second-favorite. Since the last time it was discussed on this site, it got new suspension and skid plates. It became the true hero of Upstate New York adventures and dominated heavy snow falls like it was a snowmobile. The car grew on me too – it was sharper with the RalliTEK springs and Whiteline control arms, but it ultimately couldn’t over come it’s biggest flaw – something that’s not even the poor car’s fault. I blame Subaru of America every day for not offering this car with a manual transmission. In 2021, I sold it. Maybe one day it’ll come back into my life.

1: 1997 Jeep Cherokee 2dr Sport 4.0 4×4 stick

Objective ranking: 5

This is vehicle “number 10” – the one that made this list possible to begin with. It’s a manual transmission 4.0 4×4 Jeep XJ. It also has a factory applied stripe along the side – the first vehicle I’ve ever owned with graphics. Two years into owning it, I tried selling it because it was too good to keep. Then my better half learned how to drive a stick shift with it, fell in love, and it became hers. I’ve since rekindled my love affair with this thing and hope to hold on to it for a long time. But, more on that later.

Objectively though – how could a bare-bones two-door solid axle 4X4 from the late 20th century outgun a flat six Subaru!? Or be a better commuter car than a stick-shift Civic!? Or, be a nicer thing to own than its automatic four-door cousin with power windows!? And yeah sure, the 4.0 is an engineering marvel, but is it really more bulletproof than a EJ22!?

Come on now – we have other people to think about after all…

(yeah, right!?)