alt Hacker NewsI think what makes them work (for me too!) is that they're not simply random for the sake of being random. They're a oddball but there's clearly a shared theme/style and they're well-executed.
I'm not sure I'm interested in anything they're selling, but after what felt like 15 years of "young California hipster", I think this style catches my attention at least somewhat.
I remember reading somewhere that to target gen-z/alpha advertising shouldn't be direct or in your face but instead present things in an "organic" way that makes it seem cool, without the appearance of trying too hard to sell you something.
I guess the target audience they're going for is people who already have iPhones/iPads but would have bought a chromebook for school instead. This seems to be a reversal from their previous "what's a computer"-style ads that tried to sell iPads as the replacement for personal computing.