Rob’s Top 5 Rolex Watches EVER — The Best Of The Best

As far as contentious Top 5 lists go, this is about as divisive a topic as I can think of. My Top 5 Rolex watches EVER. And yeah, you really do need to SHOUT the “ever”. Why? Because if you go into a list like this half-cocked, you’re going to misfire. You have to be 100% convinced (and bloody-minded at that) to even pretend that you know what the Top 5 Rolexes in history are. Luckily for you (and for the activity in the comments section, no doubt), I am both those things.

The funny thing about anointing myself the international arbiter of Rolex watches is that I don’t actually own one. I never have. I’ve always wanted one, but these five watches are actually to blame for me never pulling the trigger. Why? Because when you’ve seen such wonder, held such beauty in your hands, felt the metallic kiss of perfection on your yearning wrist, dropping around 10k on a (barely available) lookalike just doesn’t wash. Not for me, anyway.

If I’d expanded this list by one more place, the bicolor 36mm Datejust would have made an appearance. That will likely be my first Rolex because of its blessed ubiquity. But forget that nonsense. There were only five slots. So here they are, in reverse order: Rob’s Top 5 Rolex Watches EVER.

5. Rolex Daytona 6240

Yeah, I know — a Daytona on the list and it ISN’T the Paul Newman. Big whoop. The “Newman” dials only got so popular because of a weird twist of fate that saw one of those initially unloved references land on Butch Cassidy’s wrist. Their scarcity (because they weren’t produced in great numbers) added fuel to the fire and here we are. Locked in the bizarro universe that treats a hammer price of nearly 2 million for a failed watch design as the norm. Go figure.

I’m a Speedophile…

Everybody with taste knows the 6240 era of Daytonas is the best. You can quibble over big text, small text, black dials, silver dials, retailer names on the dial as well or, in some cases, nothing but the word “Rolex” all you like. If you’re having that argument with someone, stop, buy each other a drink, and pat each other on the back. You’re both right. This here is the real legend among legends. Choose your flavor as you will, but the configuration is to die for.

I would accept one challenger (but only because I’m a Speedophile). If you threw an early reference 6239 in there with a black dial, white sub-dials, a steel bezel, and a pump-pusher case (which reminds me of my own Broad Arrow Speedmaster) I’d listen to your argument patiently.

Then I’d tell you to buy a 1998 Broad Arrow and a condominium in Tijuana instead.

4. Rolex Day-Date Reference 228235

I will admit that this is a ridiculous curveball, but please, hear me out. The Day-Date deserves to be on this list somewhere. Even Rolex describes is as its most “prestigious” wristwatch. That’s high praise coming from the Crown. And while the full yellow gold Day-Date is perhaps the classic in the range (and a wonderful, timeless choice should it be yours), it is not the best.

A lesser-known reference released at Baselworld 2015, it barely gets any attention.

I’ve been hung up on the Rolex gold and champagne dials for years. I was so obsessed with the combo I wouldn’t look anywhere else when trying to pick a Datejust for myself. And then I saw a “corrugated” face in RJ’s Pre-Owned Picks last week and it changed my life. I started looking for other Rolexes with this style of display or decorated with vertical lines. And I found one. Pinstripe perfection in rose gold, no less. The Rolex Day-Date reference 228235 is a killer. A lesser-known reference released at Baselworld 2015, it barely gets any attention. Don’t ask me why. I think it’s the fourth-best Rolex ever made…

3. Rolex Explorer II 1655

Okay, okay. I’m reining it in now. You must have expected the 1655 to pop-up on this list, no? Well, let’s face it, it’s either landing on a Top 5 or a Bottom 5. It isn’t exactly “middle-of-the-road” in anyone’s book.

I know it isn’t universally loved. Some people can’t stand the busy dial and think it is a headache incarnate. I think it is pure heaven. The diameter kicks the modern Explorer II’s bloated case to the curb. And that complex lume pattern? Well, it’s the stuff of dreams. Fever dreams, maybe, but this one will endure for many moons yet. Good luck getting one on your wrist if you happen to agree with me.

2. Rolex GMT Master 6542

Let’s go back to the beginning, all the way back to 1954 when Rolex launched the GMT Master line. Forget everything you know about the modern GMT Master II — the successor to this model. Forget it. Everyone has an opinion on that watch. A lot of those opinions are negative because it is the poster child for “managed scarcity”. It’s a bit of a sore point for many people who just want to buy a good watch with a nice red and blue bezel.

But imagine if you could step through a door to 1954 when the very notion of watches being luxury items was alien. Imagine you were looking at this object as a functional tool and nothing more. Truthfully, this watch is beautiful in any context or any scenario you drop it into. But I think it’s real majesty shines when you decouple it from the rampant BS that floods the watchmaking industry and you just take a step back and look it as a thing. It is a triumph of texture and color. It is the perfect marriage of form and function. And it has a bakelite bezel.

“Pussy Galore”

Better still? Its nickname is the “Pussy Galore”. This timeless moniker works on multiple levels. For those of us who remember the film, it makes perfect sense. But it also works for Gen Z kids that probably interpret it as a promise of things to come, should they wear this watch to the gym (or wherever it is they hang out these days… TikTok or whatever…).

1. Rolex Submariner 6536

For me, the Submariner 6536 from 1955 is the quintessential dive watch and the greatest thing that ever ticked. Enormous lume plots, a refined gold/white colorway on the black dial, slim, drilled lugs, a comfortable rivet bracelet, a no-nonsense bezel insert, and, best of all, no f—ing crown guards.

When you sit this beauty next to a modern-day sub, it is really, really easy to see how Rolex got its reputation. It is also fair to question, upon totting up the noticeable differences between the current model and 1955 version, whether the company’s modern products would be anywhere near as desirable as they are were it not for the existence of models like the 6536 in the back catalog.

…the greatest Rolex ever.

In the same way that the notion of a brand’s luxury can penetrate your subconscious through smart product placement, is our appreciation of modern Rolex watches ever entirely free from the memory of the brand’s glorious heritage? I’m not so sure it is. And, with a couple of notable exceptions, that’s why I’m looking to the past for my first Rolex buy.

The 6536 has a 6mm crown sitting there, proud as punch, on the side of the case. It gives the watch a much more natural character than the models polluted by crown guards. The 8mm crown of the 6538 is perhaps even more awesome, but borderline cartoonish. That and that alone handed the coronet to the 6536, the greatest Rolex ever. But what do you think?

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