Successful pioneers are always quick to discover that imitation follows hard on the heels of flattery. These days the idea of giving something with more than two doors a lowered roofline and then claiming it is a coupe is no more radical or original than fitting it with a wiper stalk. It’s a trend that has inspired some truly horrendous-looking cars, several of which have worn Mercedes badges. Yet one glance at the first-gen CLS which kicked the thing off shows just how good the chop top can look on something long, low and sleek. It’s a genuine shock to realise that such a fresh-looking piece of design is on the cusp of its 20th anniversary.

Before anybody gets too het up, I appreciate that Mercedes didn’t pioneer this part of the market. At the original CLS press launch several British journalists demanded to know how Merc’s claims to be breaching a new segment squared with the fact Rover had done much the same thing with the P5B Coupe nearly 40 years earlier. The blank expressions on the faces of the Merc execs suggested they were entirely unaware of the Rover’s existence. But it is fair to say that, until Merc reanimated it, the idea had been in long-term hibernation.

While its innovative styling gives plenty of opportunity for black polo neck nerding, our Pill has been carefully selected for another very obvious point of appeal. It dates from the happy time when Merc was still putting big engines into cars without demanding buyers also went for an AMG version. So while most British CLS buyers opted for the V6 diesel, our Pill is packing the much more compelling option of the 5.0-litre ‘M113’ V8. This is in a relatively relaxed state of tune – making 302hp, and likely some muscular noises as it does so – and always suited the CLS especially well. Even after 18 years and 112,000 miles this one should still have most of that muscle left. For £4,500 it looks like excellent value compared to the dowdier Merc V8 alternatives for the same or less.

While the stylish exterior is entirely different, the C219 CLS has a very close relationship with the W211 E-Class under the surface. Mechanically they are pretty much identical, with the CLS sharing its dowdier sister’s wheelbase and sitting on the same floorpan, with common suspension components, engines and transmissions. So the good news is that parts supply for the oily bits is every bit as good as it is for the contemporary E-Class.

But there is a negative side to the shared heritage as well. Like the E-Class, the CLS is a product of Mercedes’s long era of shonkiness, the period throughout the late nineties and noughties when the brand gave up on solidity and reliability and to prioritize snazzy new technology, the ambition to fit this often running far in advance of the corporate ability to make it work.

Being a well-equipped CLS 500 our Pill is going to feature most of the available failure points, including both the Sensotronic electric brake booster that is infamous for expensive borkage as well as height variable AIRMATIC suspension. On the plus side, this is definitely working at present, the vendor demonstrating its potency by having selected the raised ride height setting, which is why there seems to be about two inches too much space at the top of the wheelarches. But AIRMATIC is also well-known for pricey pump failures. Squinting at the interior shots also suggests our Pill has the radar cruise control which would have been another £££ option at the time, as well as the bi-xenon headlights. It seems fully laden for a non-AMG version.

While the CLS was given keener chassis settings than those of the E-Class it was still much more of a cruiser than a bruiser, especially on air suspension. The driver’s seat position is indeed low and coupe-like, and from memory the C219 steered pretty nicely. Less impressive is visibility – hindered by the front pillars and pretty much wiped out rearwards by the letterbox rear screen. Legroom is respectable, pretty much identical to that of the E-Class, but the fashionable roofline means that taller occupants struggle to fit comfortably in the back. Which must have been inconvenient to any of the Russian gangsters drawn by the car’s visual menace and wanting to transport a full cargo of hefty henchmen.

Our Pill’s MOT history resembles the flag of Burkina Faso – near equal amounts of red and green. The good news for a Merc of this era is that there is only one reference to any kind of structural corrosion, which is reassuring given the C219 shares the tendency to rust as its less snazzy contemporaries. The single mention was an advisory for a grotty front sub-frame in 2020, this of the milder ‘not seriously weakened variety.’ Apart from that the only use of the c word in the online history has been in reference to brake pipes and exhaust brackets.

More concerning is a fail with an airbag warning light illuminated in 2017, one that hasn’t returned since, plus a ‘fuel system component leaking’ in 2020. Aside from those there have been several other flunks for worn suspension components – the C219 being well-known for the rapacious consumption of bushes and control arms – as well as mis-aligned and nonfunctioning lights. Keeping the suspension in fettle is likely to be akin to painting the Forth Bridge – as soon as you’ve replaced everything it will be time to start again.

Yet that need for care and attention is definitely priced into our Pill, which is just an ageless registration away from fooling Daily Mail caption writers into thinking it’s worth at least three times as much as it is. It certainly looks much fresher than any of the other Mercs you could buy wrapped around the same engine. In short, a very stylish way to get a dose of valedictory value fun.