My Car History: Reilly Brennan

1986 Toyota Corolla LE: Bought off an exec at Federal Mogul for all $2000 that I had saved since my first holy communion.

1987 Volkswagen Jetta GL: White with black houndstooth interior and black plastic moldings. I modded it a bit with some Neuspeed parts and a Techtonics exhaust. My favorite car.

1981 Volkswagen Rabbit diesel: Bought for a few hundred dollars and stored in my friend Andy's mom's garage. It never ran. We drank beers in it and pretended we were on a rally somewhere.

1986 Alfa Romeo Spider Veloce: Bought in Florida from a retiree with a vanity plate on it. My dad and I flew down to Palm Beach with $6000 in cash in my underwear. Trouble free (honest).

1986 Volvo 240 wagon (245): Silver, manual, blue vinyl seats. Incredibly solid—like you read about. I miss this car. During a photoshoot before I sold it to my friends, I had a dozen skateboarders in Ann Arbor olly on, over, and off of it, terribly damaging its bodywork.

1977 Ford F100: Bottle green, rusty, barely ran. Bought for $500 and kept in my friends’ backyard along with #7-9.

1977 Honda Civic CVCC: White, adorable, reliable, and I’m really glad I owned it. (1974 Model shown here.)

1986 Chrysler New Yorker: Purchased from an Ann Arbor lesbian (the best kind) and never ran. Sat in the street until it was towed. No idea why I bought it. (1988 model shown—yes we know it has different headlights.)

1986 Chevrolet Celebrity Eurosport: Bought for $500 and run hard for about six months. One day Seyth (yes, Winding Road editor) and I were trying to drive it fast in reverse and I lost control and hit a tree. It caught on fire, the cops came, and I paid a towing bill higher than the price of the car.

1989 Range Rover County SWB: Bought in Vermont on eBay Motors and driven back to Michigan in the worst snowstorm of 2001. Engine was trouble free and I loved the brown/brown/brown colorway. Lots of broken interior bits and pieces, though, and had an interior fire (!) before I bought it for $2000.

1995 Nissan Pathfinder: I finally bought a car built in the 90s. 4000 bucks, crimson red, reliable, and one of my favorite SUVs of all time. Still miss this thing.

2005 Jeep Grand Cherokee: First year of the WK. I had been a GC fan boy for so long and this was the first new car I ever bought. Leased it for $249 per month because my friend worked at Chrysler. 2007 Jeep Grand Cherokee: The same exact car, just black. Love this era of GC despite the fact that nobody else seemed to think highly of it.

2009 Subaru Forester: Really my wife’s car. White, relatively boring, but I still liked something about it. I wouldn’t buy another from this generation, though. At least it had an automatic and not the CVT.

2009 Honda Fit Sport: Now that we're in San Francisco, the allure of 40 mpg on regular gas and a small parking footprint was too hard to resist. I went for my favorite small car from the brand that I feel makes the best small cars.