About a decade ago, Apple ran a series of adverts featuring the comedians Mitchell and Webb, designed to highlight the difference between Macs and PCs. The ads didn’t bother explaining what the spec differences were, or even showing you pictures of the products they were advertising (Alan Sugar would have fired the bladdy useless lot of ’em on the spot). Instead, Apple’s whole purpose was to point out how much cooler its computers were compared with PCs.

On the left, David Mitchell was in full Mark Corrigan-mode as the PC, wearing a brown suit and explaining how family holidays are best represented in pie-chart form. On the right, Robert Webb slouched around with his hands in his jeans, breezily explaining how effortlessly creative he was as a Mac. It wasn’t a great advert series. It was smug. It was annoying. And it made you realise that Apple didn’t understand Peep Show. (People rooted for Mark, and Jez wasn’t cool. Super Hans using his MacBook to order psilocybin on the dark web would have been cool, although the Advertising Standards Authority might have had something to say about that.) But you accepted the point: PCs were stuffy, out-of-touch, virus-ridden machines suitable only for grey office drones to run spreadsheets on. Your dad had one, and it kept freezing whenever he tried to show you the email he had received saying he was due £5,000 compensation as the victim of a road accident. The Apple experience, on the other hand, was a constant dress-down Friday full of pictures, music and movies.

The reason Apple got away with this ad was because it was – undoubtedly – a very cool company. Throughout the 00s, it changed the way we consumed entertainment and shaped the ways in which we interacted with each other. What is more, it did so in the form of nice white curvy things that, compared with the grey/black boxy PCs, made the world seem a better place (if, by better, you mean a permanent episode of Black Mirror where we would sooner press handheld blocks of plastic than converse with our friends and family). Apple was so cool it had a quasi-spiritual air, with feverish launch events and a leader who singlehandedly pioneered normcore. Compared with all this, what did Microsoft have? Clippy, a crudely animated paperclip that was supposed to help you write covering letters.

The distressing news, then, for people who have spent approximately the economic output of Moldova on Apple products over the past two decades, is that Apple in 2016 no longer seems very cool. In fact, it now seems a bit of a mess, as out-of-touch and unfriendly as Mark Corrigan. Its products look increasingly samey or – worse – plain ugly. Its innovations, such as the Touch Bar, look like the kind of thing a toddler might come up with at an hour’s notice (“Put some iPad ... here!” *toddler points above the number keys on a nearby laptop*). It raised its already extortionate prices to cash in on Brexit (technically our fault that one, but still). And it seems to be on a mission to make everything as incompatible and user-unfriendly as possible. Currently, Apple is selling a whopping 17 different dongles for all the different bits its devices no longer serve properly. Meanwhile, its compatibility is a car-crash example of capitalism gone rogue: even the iPhone’s new standard Lightning headphones won’t connect to Apple’s latest line of laptops without an adaptor. It all points to a grand strategy whereby come 2036 you won’t be able to type at all without special gloves that have to be individually purchased to fit each finger, and then will only allow you to spell out the word “plonker”. Where once Apple had an app for things you didn’t imagine were possible, now it has a dongle for things that were perfectly possible before you needed a dongle.

Oh, and on top of all this, it has now got a CEO called Tim (embarrassing) who wears a fleece and doesn’t seem to think he’s Jesus. It’s all wrong.

But if Apple’s cachet is fading, who does that leave us with? Surely not Samsung – its phones literally blow up in your hands. Step forward ... Microsoft and Bill Gates! Once, he was derided as a squeaky-voiced billionaire who couldn’t possibly be as cool as that guy who tucked his roll-neck shirt into stonewashed dad jeans (weird times, looking back now). These days, Microsoft’s co-founder is doing some pretty cool stuff. Such as pouring his billions into philanthropic projects fighting malaria in Africa. And helping to eradicate poverty. Of course, ending life-threatening disease is only technically cool if you can make nice, shiny computers on the side, but Microsoft seems to be sorting that side of things out too. At a recent launch event, it turned its attention to the world’s “creatives” – tempting designers and musicians to cross the bridges and start taking a Surface Pro to their nearest organic coffee store. Is such a shift really possible? It could be. After all, even Clippy seems to have harnessed his valuable retro appeal of late, starring in memes with all the nonchalance of a piece of animated stationery who always knew he was about more than page indentation advice. Have the tables turned? Has Mark finally got the whip hand over Jez?

The ball’s in your court, Apple. You were cool once. But now you need to sort out your products and at least try to end measles. Failing that, how about making something we can plug a USB stick into?