The R231, which ran from 2012 to 2020, sits at the bottom of the heap for SL Mercedes for a few reasons. First, it’s just kind of awkward looking. Mercedes was going through this quasi-baroque styling period and some models wore it better than others. The model also wasn’t all that dynamically interesting. It was big and heavy, thus negating both the S (Sport) and L (Leicht or light) in its name.

It gets worse. This is the first SL since the introduction of the V12 to Mercedes lineup to not be available with that engine outside of AMG models. Also, the base V6 was a snoozer. Don’t get me wrong, this isn’t a terrible car on its own, but in the company of its kin, it comes off as the poor cousin.

R121

The 190SL feels like the 300SL equivalent of that meme where you ask your mom for something at the store and she tells you that you have it at home, only the one at home is bad. It takes all the best parts of the famous Gullwing and immediately disregards them so all you’re left with is a slow little convertible that almost looks like its big brother.

The R121 chassis, as it was known internally, debuted in 1955 and was powered by a carbureted 1.9-litre engine making 105 horsepower. Unlike the Gullwing, the 190SL didn’t have a cool spaceframe chassis, instead using a cut-down version of the W121 sedan. Despite that, it had a similar fully independent suspension setup and was a lot less expensive than its bigger sibling.

Ultimately, while this is a classic, and a handsome one at that, you can definitely get more SL for your money.

R230

The R230 was introduced at a rough time in Mercedes’ history. It was part of the new wave of Benzes that ditched the restrained styling and legendary build quality of the cars from the ’70s, ’80s, and ’90s in favor of dramatic lines and huge horsepower figures.

The R230, which ran from 2001 to 2011, did look cool and models like the SL55 and 65 still inspire folks to make questionable decisions today. The issue is that not only did they retain some of their predecessor’s (R129) bad habits, namely the ABC (automatic body control) hydraulic suspension system, but they also introduced new ones like brake-by-wire systems that just time out after a certain number of brake pedal depressions.

These cars are still pretty cheap and while keeping them on the road is expensive, in true SL form, they are awesome cars that offer real performance and superior comfort.

R232

The current R232 generation SL, introduced in 2022, is awesome. It’s super luxurious, comes with a couple of great drivetrain options (and one crappy one) and looks incredible. It’s also all-wheel drive only, super heavy, and cataclysmically expensive.

In many ways, the R232 represents a return to form for the SL line . It’s an instrument that’s been relentlessly engineered to be as good a grand tourer as Germany can possibly make and it makes it easy to forget the blandness of its predecessor.

All the nice things I just said pretty much go out the window, though, with the SL43 which is a very ill-conceived car that should not exist, and which waters down the SL’s place as a flagship in Mercedes’ lineup. Four-cylinder engines, especially obnoxious ones, don’t belong in SL-Class Mercedes.

R129

The R129 faced a nearly impossible task when it debuted. It had to help sell a very new and different face that Mercedes was trying to adopt to its most influential customers. Its predecessor defined the terms luxury and excess for 18 years and now this new, bigger-bodied, comparatively slab-sided upstart has to come in and redefine them. Not enviable.

Only, the thing is that the R129 (1989-2002) actually succeeded. It did such a good job that people still look at someone driving around in one and think, “Wow, they’ve done well for themselves.”

The R129 also marked the introduction of the V12 engine to the SL in the form of the SL600, and the V8 version, dubbed the SL500, was almost as good. These cars were sophisticated, understated and why don’t I own one now?

R107

With the exception of the 300SL, maybe, the R107 is the car many people think of when they think of Mercedes SLs. The car existed for 18 years with remarkably few changes aside from engines and that says something. The Paul Bracq styling is iconic and looks as good now as it did when it debuted in 1971.

Sure, the R107 is kind of slow even in its most potent Euro 500SL trim, and, sure, it’s very softly sprung and has a city bus-sized steering wheel, and, yes, it rusts like crazy. Still, this car did much of the work to build the reputation that Mercedes has today. These cars were built like bank vaults and the fact that you still see them regularly on the road in sunny environs is a testament to that.

W113

The second-generation SL got its nickname of ‘Pagoda’ from the way the hard top roof looks as you view it from the front, a bit concave. It’s also arguably from a golden era of Mercedes design when Paul Bracq was cranking out beautiful, elegant and understated cars like his life depended on it.

The W113 SL was available exclusively with inline six-cylinder engines, either carbureted or mechanically fuel-injected. It could be had with a four or five-speed manual transmission or a four-speed automatic, and while it was nothing like the SL that preceded it in terms of outright performance or exclusivity, it set the tone for the badge going forward.

The Pagoda SLs are still sought after today and easily rank among the prettiest cars from their era.

W198

There was never any other way for this ranking to end. The 300SL “Gullwing” has gone down in history as one of the world’s most desirable cars thanks to its combination of jaw-dropping styling, those iconic doors, and then-unheard-of performance.

The W198 Gullwing gets its performance from a few places. First is its engine, a mechanically fuel-injected 3.0-litre inline-six borrowed from the 300-series Adenauer limo. It was paired with a four-speed gearbox and produced 240 horsepower. That, coupled with a wildly unique, race-car-spec tube chassis and independent suspension meant that there was nothing on the road in 1955 that could keep up with the Gullwing.

These cars are worth millions of dollars in 2024 and given their history, their looks and their still-impressive performance, they seem worth every penny of that and more.

This story was first published on Robb Report USA