Imagine this for a second. After working away for a number of years and reaching a moderate level of success, you’re hit with an incredible stroke of luck. Whether it’s the successful sale of the business you built up from scratch, a big lottery win, or the passing of a distant-yet-wealthy relative, suddenly the idea of having to maintain any kind of budget for anything has lost any relevance. So far, your lust for a performance car has remained mostly constrained to the relatively attainable Porsche 911 or maybe the new Corvette, but you’ve never thought about the many goodies that can be had if you bump the budget up closer to the $200,000 plus benchmark. Now that you have the means, the question is, where does one even start?

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In the upper echelon of luxury performance cars, the idea of the “apples to apples” comparison is often much less relevant than in any other segment. How fast a car can be stays relevant to a degree, but once you crest over the $200k mark, the most important question is what makes the car so special, whether in levels of craftsmanship or right down to that emotional level of what makes people gravitate to one particular high-end brand or another. With that in mind, I set out to get my hands on two of these premium GT cars—the Bentley Continental GT V8 and Aston Martin’s DB9—in order to get a better understanding of what has made them so successful at prying significant dollars from the bankrolls of the urban elite.

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While both the DB9 and Continental GT V8 make a significant statement with their exterior styling, they were clearly penned with two very different aesthetics in mind. Looking around the bold and imposing sculpture of the Bentley, I’m initially considering calling it conservative, but that isn’t an accurate definition. The Bentley’s coachwork is incredibly architectural, with every bodyline building on the next to create something quite stunning. The end result is a subtle coupe that passers-by will stop and stare at because of its shape, more than because of how fast they can imagine it going.

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The DB9, on the other hand, is chock full of styling details that speak to its ability to rocket off into the sunset. The first few clues around the exterior are the carbon fibre accents on the Aston’s mirror caps, front splitter, and rear diffuser. Every speed-freak on the planet seems to be in love with anything clad in carbon fibre, so these details will be quick to draw attention. Beyond the lightweight bits, the DB9’s sleek profile definitely looks like something penned with both style and good aerodynamic properties in mind. From its gaping front grille to the slight slope to its trunk lid, the DB9 does an interesting job of balancing form and function a touch more than the big Bentley offering.

The passenger cabins of both cars are very well executed to say the least. There is probably an entire heifer’s worth of leather in each cabin, and just about every knob and switch feels appropriately substantial given the price of entry. For fans of colour, Aston provides a plethora of interior options in which to deck out your interior. If you want the dash and door panels to be one colour and the seats to be another, but you want a third contrasting colour for the stitching, they would be more than happy to comply. On the other hand, Bentley has a handful of stitch patterns for the seats and leather trim that all look great; I’m rather partial to the black quilted leather found in our test car. Regardless of combinations I’d be quick to give the win to the Aston on this one. Even in its most conservative combinations the overall styling in the interior is simply top notch, right down to the acrylic layered buttons and the pen built into the dashboard.

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As in any segment, many buyers want the latest and greatest in terms of technology packed into their luxurious new ride. Fortunately for Bentley, their relationship with the Volkswagen Audi group means they have a slick and seamlessly functioning infotainment system that takes care of all things audio, navigation, and communication. I’ve been a fan of the system in VW and Audi’s product lines, and that has not changed with its integration into the Continental GT. As soon as I’d hopped in the car I had my phone connected, was streaming Bluetooth audio, and had punched in the coordinates to our hotel 20 some-odd miles away.

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My experience with the DB9 wasn’t quite so seamless. Whoever put together their user interface was either from another planet, oh was given a very interesting set of instructions. A number of buttons on the interface run dual-purpose, depending on whether you’re trying to control navigation or audio, and every time I thought I had the system figured out I managed to press the wrong button and was back to square one. My only speculation is that the system was purposely designed to be annoying in order to keep drivers focused on the important stuff: the car’s beautiful interior and the roar of the car’s 5.9L V-12 engine. To be fair, if I was shopping for anything in this category I really wouldn’t be letting infotainment capabilities sway my decision. There are so many strong points in the DB9 from tip to tail that as much as I got annoyed with the system I was more than happy to just not use it.

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The next step in our escapades with these two pieces of hot hardware was to hit the strip and see how they handle the urban jungle. When looking at high-power coupes there’s always a wonder as to how they handle being light-footed around town. This might not be one of the main criteria while being built, but almost every performance car will eventually be found cruising city streets at a pace slow enough to be sure that everyone sees it coming. We couldn’t help but capitalize on a bit of our time in Los Angeles to roll out and see if we’d be cursing either car in stop-and-go traffic.

Of the two cars, the Continental GT V8 really felt like it was right at home crawling around town. Being of the house of Bentley means the GT can be downright numb when the variable damping and chassis settings are dialled to the softer side. The throttle pedal loses any kind of abruptness and makes inching through traffic silky smooth. This isn’t the kind of ride I’m typically a fan of, but having the setting available the morning after a night of playing high-roller on the club circuit isn’t necessarily a bad thing. Given the option I was definitely more entertained by the other end of the spectrum, allowing the twin-turbo V-8 to unleash all hell and push 500 horsepower to four wheels as I blasted from traffic light to traffic light as quick as the law would let me. The Bentley may be considered deficient in this trim with its four missing cylinders, but there’s something really intoxicating about a 4.0-litre V8 with forced induction. I absolutely hate quoting marketing material but when Bentley says “…from the distinctive backbeat of its eight cylinders at idling speed to the glorious snarl of full-throttle acceleration…” they really hit the nail on the head.

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Oddly enough, the DB9 was also decent at taking things a bit slower. It’s still more high-strung in comparison to the Bentley, but there is still a level of smoothness from behind the DB9’s wheel, regardless of how enthusiastic you’re feeling. It is pretty quick to encourage its drivers to haul ass at every opportunity, mind you, but if you wind up elbow deep in gnarly traffic the DB9 isn’t tough to drive smoothly. The one thing to consider between these two cars is how much time you really plan on driving it in and around town. The Aston can easily handle it but it also has less ground clearance, which calls for added caution rolling in and out of driveways and over speed bumps. It is also a touch more tricky to park compared to the Bentley, even though both came equipped with parking sensors and a rear-view camera.

Although you wouldn’t guess it, both the Continental GT V8 and DB9 deliver a relatively comparable level of grin-inducing fun when driven at a leisurely pace. Sure, they have their glaring differences but when kept fenced within the boundaries of well-guarded public roads their differences in terms of performances are subtle. Not one to be content with “quick enough,” we set out for that sexy stretch of the Pacific Coast highway heading north from Santa Monica to give these two cars a proper shakedown. From the very first bend the Aston Martin started walking away from the Continental. What was once a duel of two dissimilar twins rapidly shifts into a tale of Billy and his adopted half brother. At the wheel of the Aston every corner has me picturing the notorious bends of the Nurburgring and eyeing up the apex. With an open road ahead there is no such thing as taking things lightly and being a Sunday driver. The world suddenly breaks down to a simple equation of you, twelve screaming cylinders, and as much tarmac as you’re willing to claw down before the day is done.

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The Continental GT V8 invokes a completely different set of ideals when the road opens up. Rather than turning the world into the Rolex 24h at Daytona, there’s a sense of boundless adventure that comes from the GT. Within the first few minutes, what were once grand machinations of a cross-country drive suddenly come back to me, and when we creep up on our turn-around point I start wondering how much further it would really be to push on to San Francisco. In a way, you could say that that the Bentley is more about the destination and the Aston is all about the drive. That’s not to say that you can’t bury your foot in it and be an all-out hooligan at the wheel of the Bentley and be quite satisfied with the result; it is able to deliver on that end of the spectrum but the more I look at it, the go-fast goodness is kind of like the icing on a very luxurious cake. In hindsight, this is very much in line with how the DB9 is able to be a civilized and easy-to-drive cruiser. That wasn’t the primary focus while building it, but it is a well-executed bonus trait.

Much like the world of fine food and wine, evaluating vehicles at the upper end of the register is brutally subjective. Sure we could nitpick away at performance stats, features-per-dollar, and all that other mind-numbingly rote information and boil it down into an equation of checks and balances; but by all accounts I’d much rather watch the polar ice caps melt. If you find yourself in a position of good fortune and it’s time to pick your new ride I’d start by hopping behind the wheel of a few of them and simply see which speaks to you. For me, it would be the DB9.