John is 40 and has never, ever bought a new car. He is still driving the faithful Corolla he had in college. But the time has come for a serious upgrade, and it must be something that his 4-year-old car addict son thinks is awesome. What car should he buy?

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John wants to foster a passion for driving in his kids now that he is ready to upgrade is trusty old Toyota to something a bit more interesting.

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Here is the scenario:

I’m an almost 40-year-old lawyer/father of 2 and have never purchased/leased a car in my entire life. My first car was the family ‘96 Corolla, which I drove through college and law school. Loved that car, until the transmission went out due to neglect. I met my wife in law school, who drove a ‘01 Corolla S (The S provided no actual performance advantage).

I continue to drive that Corolla to this day, and it has been a loyal and reliable daily driver for 15+ yrs. It has 3 huge scratches from my wife backing into concrete pillars, softball dents, and it was backed into by a garbage truck in Davis, CA. The windows, locks, center console, driver side handle, and cup holder don’t work anymore but it has had ZERO major issues and almost 200k miles. I drove my daughter home from the hospital in this thing and turned down multiple lowball offers from strangers at gas stations asking to buy it (all under $1k).

My kids are 4 and 6 now, and the 4 yr. old LOVES cars more than any human could love an object. He can name the make/model of practically every car we see, and his life goal is to own a Pagani. When we go to the airport, the only thing he wants to buy is a copy of DuPont Registry. So my next purchase will be just as much for him, as me. All my friends make fun of my car, but they can suck it because I have saved a lot of money driving my Corolla, and it has the same qualities I find admirable in people (reliable, trustworthy, safe).

I’m approaching mid-life, but this is not a mid-life crisis car. I don’t want a car that everyone else in the Valley has. I want something my son will think is cool and will be excited to drive in. This is a daily driver that I want to keep for a long time, that will retain its cool/retro charm like the NSX and 3000GT of yore. Price isn’t really an issue, and I could go above or below my range.

Quick Facts:

Budget: $40,000 - $50,000 but flexible

Daily Driver: Yes

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Average Miles Per-Week:

Wants: Reliable, unique, timeless, something that a little Jalop will love

Doesn’t want: The same old sports car that everyone in California has.

Expert #1: Tom McParland - Don’t Fight It, Embrace the JDMLyfe

John, so I’m going to take the cop-out approach and suggest two cars—but hear me out. The first thing you are going to do is go buy any nice Japanese sedan of your choice for around $25,000. It could be a Camry, an Accord, or a used Lexus if you are feeling fancy. This will take care of the four-door, reliable, safe, and able to carry two kids and two adults requirement.

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Because you have a nostalgia and an affinity for Japanese sports cars from the ‘90s, with the remaining balance you are going to buy yourself a JDM sports car. I would suggest an R32 Nissan Skyline GT-R. You can get something like this 1992 GT-R for about $27,000. Granted that specific car was sold, but there will be others. You can wait for just the right one because you have your reliable sedan to take care of your daily driving duties.

A JDM sports car will be way cooler and much more unique than whatever sporty German hardware is being leased in your neighborhood. Your son, because he is one of us, will go nuts over a GT-R. Imagine him playing Gran Turismo with his buddies and they select the iconic GT-R to blast around the Suzuka circuit. He can say “My dad has one of those!”

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You could hang onto it as a fun car to pass down to your kids, or enjoy it for a few years and probably sell it for pretty close to what you bought it for.

Expert #2: David Tracy - There’s A Reason This Car’s Such A Legend

Photo: Mike Boswell/Flickr

If you’re looking for something “cool,” the Datsun 240Z is the answer to all of your troubles. It’s arguably one of the most important Japanese cars in history, launching in the U.S. for 1970 with advanced tech that blew pretty much every other small coupe in that price bracket out of the water.

The thing came with a 150 horsepower overhead cam inline-six, a fully independent suspension (Chapmen strut in the rear, MacPherson strut up front), and a four-speed manual, all for the low, low price of $3,256. It was a superb handling car that Ben Hsu says in his book Classic Japanese Performance Cars “cemented the reputations of both Nissan and Japan as sources for superb performance cars.”

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The thing won SCCA Championships and rally races around the world. And that’s not even mentioning the car’s sleek, handsome looks. If you’re not convinced that Yutaka Katayama’s (the first president of Nissan’s U.S. operations) little sports coupe is cool, and that it has a “retro charm,” keep reading up on the 240Z. It’s a marvelous machine, and your son will love it.

They’re not all that expensive, either. You can find clean ones in your neighborhood for less than 10 large. But with your budget, you might want to pick up a pristine example.

Expert #3: Patrick George - Finally A Good Question

Oh, thank god! Someone with an interesting What Car Should You Buy? question. If I had to recommend the damn Mazda3 hatchback again I was going to swallow a bottle of pills.

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Anyway, John, you and your family sound rad. I’ll add that my first car was also a 2001 Corolla S (indeed, the S does nothing) and while it served me well with zero problems for close to a decade I couldn’t wait to get out of it and into something faster. I bought a Subaru WRX.

The good news is your $40,000-$50,000 but flexible budget offers a ton of flexibility. The bad news is you have homework to do, my friend. There are a LOT of fun cars in that price range I can recommend: a used Porsche Boxster, a gently used Corvette Stingray, a new Ford Mustang GT or Chevrolet Camaro SS, even that Lotus your son seems to dig.

It’s going to be on you to drive a bunch of stuff and buy what you like best! Get out there and do some test drives.

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But as I think about this, my mind wanders back to the post-Corolla choice I made—except you have a bigger budget than I did when I dumped the Toyota as a bored, under-employed 22-year-old. I actually think a brand-new Subaru WRX STI might be a great fit for you.

You’ll be getting your speed fix, for one. The STI’s 305 HP engine is old but it’ll still wail on a bunch of newer cars, and that’s before you start modding it, which you and the kids definitely should do. With its huge wing and bulging fenders and stick shift, the kids will love it, especially in that bright blue. As a sedan with a decent trunk, there’s few compromises in including them in your daily-driving. Plus it’s right in your budget.

As I understand it everyone in SoCal has a Tesla or a Mercedes. Here’s your chance to give them the middle finger, and your kids one hell of a ride they’ll always look back on fondly.

Expert #4: Raphael Orlove - Just Buy The NSX

All of the other cars suggested here are fine and good and wonderful. I myself am still holding on to a mental image from when I was a kid on a family trip of a man cutting through a rain-slopped Marin County two-lane in a Lotus Elise, wishing that I might someday have that steering wheel in my hands. An Alfa 4C would fill that niche, too, if you’re set on that idea.

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But I don’t think you need to tread into the skateboard-with-an-engine zone of sports cars. You already know what kind of car you want: one with a good reputation and classic charm but genuine reliability. Something like an NSX.

Just buy the NSX.

You can still find them for not-insane prices, they are easy to own (unlike, say, a Ferrari 456), and they are as good and as wonderful to drive as you think. Listen to your heart. Know it to be true.