They sounded perfect, individually, each one producing a uniquely beautiful noise that echoed throughout the otherwise empty forest. But collectively they sounded like some kind of wild monster, howling its way through the woods, occasionally spitting flames, even, at anyone who got too close. Never before had the normally subdued confines of our test track sounded like they did on that day.

Then again, when a 458 Italia meets an F40 and an Enzo on straight-through pipes, the noise is going to be pretty spectacular, no matter what piece of road you choose to compare them on. Because these are surely the cars that define the way in which most of the world thinks about modern Ferraris. Between them they represent the evolution of the supercar itself: the F40 at one end of the timescale, the new 458 Italia at the other.

Of the trio, however, it's the Enzo that takes your breath away most obviously. It looks huge beside the others, for one thing, but it also seems the most contemporary in many ways, despite being almost 10 years older than the 458.

The dramatically long overhangs of its body and the very obvious central location of its passenger cell provide it with a unique profile template; you can tell it's an Enzo from hundreds of yards away if you see this car directly side on. The design of its rear light clusters and its extraordinarily distinctive nose, which thrusts its way into the airstream as if it were designed to split it in half, also distinguish the Enzo beyond any other car, let alone any other Ferrari.

Sitting next to it, the F40 clearly looks like it's from a different era altogether – which, of course, it is – but in its way so does the 458 Italia, mainly because it's both prettier and more classically proportioned than the angular, angrier-looking Enzo. Seeing them together for the first time, the F40 having been returned to its owner that very day following an exhaustive two-year rebuild, is not something any of us will forget in a hurry.

Why did we bring them together in the first place? Several reasons. One, because we could. Two, because the 458 is one of the most spectacular cars of this year, possibly even this decade, so to truly understand its meaning we thought we'd compare it with its most dramatic of ancestors. Three, by taking a look at how and where Ferrari's most iconic cars have progressed during the past 23 years, we might also get a glimpse into where it's heading in years to come. Four, any excuse to drive an F40 again, it being my all-time favorite car…

And so it was toward the disarmingly minimalist cabin of the 1987 F40 (RIGHT) that I headed first. After the 458, which I'd arrived in not half an hour earlier, the F40 appears vaguely comical inside in its lack of luxury. There's just a seat, albeit a heavily bolstered bucket item with a six-point harness to clamp you in place, a steering wheel and a gear lever, plus a brace of the plainest instruments you'll find in any sports car. It feels even more spartan inside than something like a Lotus Elise. The purity of purpose, therefore, is crystal clear from the moment you climb aboard.

And when you thumb the starter button and the 2.9-liter twin-turbo V8 catches, the whole car moves gently to the engine's rhythm. There's no sound deadening at all, and, to begin with, the throttle response seems peculiarly soft. It needs a surprisingly big prod on the pedal to dial up sufficient revs to get it going, and as soon as it moves, the steering, having felt ridiculously heavy when standing still, bursts into life. Same goes for the clutch, which is similarly meaty underfoot.

On the move there is tire noise, transmission whine and no real refinement to the ride, which is skateboard stiff. The brake pedal needs a heroically big shove before there's much response from the brakes, and the 5-speed manual gear change is monumentally more physical in its operation than the click-and-go dual-clutch system of the 458. To be honest, the F40 feels like a bit of a shed by comparison to begin with, or at least it does when it's just bumbling along.

You do not bumble about for long in an F40, however, and when you do find the room and courage to open it up properly for the first time, you need to be ready for what's next. Because when an F40 lets rip, the rest of the world goes into reverse rather quickly. And if you're not ready to go with it you'll end up facing the wrong way, wondering how and why it all went so wrong, so fast, in about half a heartbeat.

The thing to remember about this car is that it weighs just 2,425lbs. That's why it remains such a complete and utter lunatic in terms of its basic straight-line performance. Do the math and you'll note that despite being 23 years older, the F40 is massively more potent than the 458 where it counts. It has a power-to-weight ratio of 428hp per ton, versus 378hp per ton for the Italia. And that's before you even mention the fact that it has 426lb-ft of torque, which is way more than the 458 has (398lb-ft) before you take their wildly differing curb weights into consideration.

As a result, the F40's acceleration feels, and indeed is, in a totally different league from the 458's when you dip into the epicenter of its power band between 4,500 and 7,000rpm – yet the 458 is nothing less than one of the fastest cars we drove all year. When we road tested it in July the 458 recorded 3.3sec to 60mph and 6.9sec to 100mph, yet on a straight and level piece of road it can't get near the F40 for pure thrust, even if its snappier gear change and closer gear ratios allow it to live with the old timer in bursts.There are all sorts of things that you can learn, both about yourself and the car, when you drive an F40 with enthusiasm. But the one defining lesson that it continues to teach us, 23 years after its creation, is that weight – or the lack of it – remains such a crucial factor. You can tell as much not merely from the way an F40 accelerates, which is eyeball-poppingly obvious, but from its lack of inertia in general – the way it changes direction so cleanly, the way it stops so crisply as long as you lean on the pedal hard enough, even the way it turns in.

In all these areas, the F40 still outperforms its modern-day equivalent, and there has to be something that can be learned from this – even if there would be similarly little debate as to which car you'd take on a pleasure drive; namely, not the one with the tea-tray rear spoiler or the $30k see-through plastic engine cover.

Climbing into the Enzo after the F40 is like wandering from one room into another within the museum of supercars, except the dates seem centuries apart. The steering wheel is festooned with switches for things like the traction control and lights, and the center console is similarly space-age in its design. And this particular Enzo positively erupts into life when you press the starter button, mainly because owner Paul Bailey has removed the standard exhaust, cats and all, and replaced it with a set of straight-through Tubi pipes. This saves around 110lbs in weight and makes the 6.0-liter V12 (RIGHT) sound stark raving insane.

But maybe the most interesting thing to note, apart from the din it produces, is the extra weight the Enzo feels to carry beside the F40, and to a lesser extent the 458. On the move it feels big and impossibly intimidating, with super-quick steering responses and not a lot of throttle required to get it to go, and go hard. But it also feels clumsy in its reactions after the other two, as if it lacks the agility of its smaller brethren, which is a touch odd, given that it weighs 265lbs less than the 458. 

Its paddle-shift gearbox, even in Race mode, is also hopelessly slow-witted beside the dual-clutch system of the 458. You'd happily swap it for the F40's heavier but more precise 5-speed manual. And when you start to lean on it through corners, that big, long tail feels like it might ruin your day in a big way if you so much as think about turning in on a trailing throttle.

In its way, the Enzo feels every inch as barking mad as the F40, especially under full acceleration, with its V12 screaming into your right ear, exhaust crackling like a giant bonfire on the overrun. Except, of course, the Enzo is actually less rewarding/more scary even than the F40 in extremis, because it feels like it could get away from you far more easily. And again it's the extra weight that betrays it beside the older car, which, by the way, is some 580lbs lighter.

And what of the 458? In many respects, it represents the best of both worlds, combining the Enzo's often amazing noise and performance and its breathtaking atmosphere with a big slice of the F40's red-raw driver appeal to go with it. That it does so at a price several hundred thousand dollars below that of the Enzo, accompanied by a level of everyday refinement that makes the old timers feel just that, is, in the end, the reason why we rate it as highly as we do.

There's no doubt that it's an incredible car, the 458, and the reason why is because it comes from such an incredible company, rich with historical high achievement, as this triumvirate clearly shows.

If it weighed a little less – say, 300lbs more than an F40 – it would be yet more extraordinary than it already is. And that's precisely what Ferrari will be aiming to do in the months and years to come. That's right, it's about to get even better.

Steve Sutcliffe/Autocar