Look right, I can remember retro g*mers making jokes about the Game Gear being 2big and 2heavy back in the day, probably in the 2000s. Classic Game Room watchers remember. Same for the Lynx. The Wii U's tea tray controller was derided for being beeeeg. I can also recall people saying that the PS Vita was kinda large back when it came out, which tbf it is pushing the definition of "pocketable" for the boys and takes up a lot of purse space.
It sort of felt like reality broke down in 2017. The first thing I did when the Switch was announced was make a joke about putting a Game Gear in your pocket, but suddenly nobody else gave a damn that the Switch is like ten inches long. Most dildos are not that long.... 
I get that it's a hybrid, but suddenly the dynamic shifted from "if it can't fit my dude pockets it's no good!" to "aw yeah bruh just get a hardcase and throw it in a backpack!" I do support backpack gang, but you almost may as well get a laptop at that point.
Handheld size has become progressively more comical over the years though, with my favourite example being the Steam Deck which is actually considerably longer than a Wii U Gamepad at an XL 13" 
Tell ya what, I couldn't fit that!!
I'm not really against the existence of larger handhelds on its own, I have long fingers and a DS Lite or PS Vita will give me handcramps sometimes. But it's like a weirder version of when all phones became "phablets" and impossible to use with one hand, suddenly all handhelds are as big as the Wii U pad. (Switch Lite excluded, though it's still larger than a Vita) It also seems like the PS Vita and 3DS primed everyone to accept hilariously short battery life? The PSP 3000/Go and DS Lite/DSi could get anywhere from 8 to 20 hours depending on your settings, that was awesome. The 3DS and Vita won't hold out for more than three hours under duress, though. Most modern portable PCs have worse battery than that, even...
I guess I'm just wondering wha happun??? I know there's a large contingent of people who never take handhelds outside the house anyway (based) and just use them on the couch, but I don't think the Deck would be much more pleasant to handle in an armchair or whatever. That's one thicc-ass boi.
Nintendo killed it
It may hurt to acknowledge this but nobody but Nintendo ever made a truly successful handheld game system
The PSP sold a cool 80 million units, which is why they made a PSP 2 =) PSP was such a banger, loads of cool games, Idk. I can agree that the GameGear and Lynx flopped tho...
I have a PSP, my original PSP-2000 from back in the day. I like my PSP. But it was up against the DS, the most successful handheld of all time. It was never really a threat to Nintendo's eternal domination of handhelds.
Which is too bad, really. It could have been literally the best gadget on earth if Sony hadn't hamstrung it with proprietary formats, a $200 smartphone in 2004.
True, Nintendo literally never faced stiff competition from anybody... Nerds were on GameFAQs and Neogaf talking about the PSP about to steamroll the DS... still, it was a pretty big hit for Sony.
Also Sony fuckin loooooves the proprietary way too much. They could have just used SD, and then Micro SD on the Vita, but weh. Also I think the cards offset the cost of the system somewhat fwiw...
Not just the cards, imagine the timeline with like UMD drives for PCs, ultralight laptops, etc.
UMD was funny but so pointless! Video format! lol
It could have been not-pointless if it were as versatile as DVD, if you could just buy burners and blank discs for it. There were some really neat japanese market only minidisc gadgets, micro-notebooks, media players, ereaders, all kinds of stuff that could have been even better with 1.8GB UMDs. From the day I bought my first PSP in 2004 I wanted a UMD burner for my PC but they refused to ever make one.
"""Universal""" Media Disc my foot.
Sony probably quaking in fear of potential piracy, really dumb...
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Sure, but it's not really properly a handheld. Yes, you hold it in your hands, but I agree with the premise here that handhelds should be pocketable.
Also, the Steam deck's total sales are closer to the N-Gage than the GBA.
Or at least fit in a purse, and I've had purses big enough to fit small laptops, that would not accomodate a steam deck