Last time we've seen a mask with a good design and a bad voice, and I couldn't choose a score for him. Now watch me do the same concept but flip it on its back. And that's because I'm incredibly biased.
Pineapple here is the first "object-head" we get on the Masked Singer - my top choice when it comes to anthropomorphizing non-living* beings, and one of my favourite character design ideas in general. He's got sunglasses with the colours of the sunset on the sea and a pet parrot I bet he takes VERY good care of, with plenty of space and proper enrichment. He's also got fake abs that don't even match with the rest of his yellowy skin and the biggest stupid grin ever. He's dressed with a Hawaiian shirt, swimming shorts, flip-flops, and has a huge straw (complete with paper parasol) stuck on one side of his head.
Pineapple is a beach bum, one of those jocks who can't wait for summer to play volleyball and attempt to surf on a beach where the waves don't get high enough to make surfing a viable thing, and I love that.
*well, pineapples come from plants, but that's a whole another can of worms we're not opening up today
Here's a heads-up: if you wanted to hear a powerful, heartrending version of I Will Survive, you won't find it here. Pineapple here sings exactly like the jock I described above, and he didn't go through High School Musical, exactly.
But oh lord look at that performance. Look at the usual beachy scene and then suddenly a hurricane appears and look at all the backup dancers going nuts while Pineapple doesn't give a single fuck and keeps on singing. But not even in the badass way. More like he isn't even aware of his surroundings (which, given costumes obscure so much of your vision, is probably true). It's such a fun performance, and Pineapple's (lack of) involvement into it makes it even more amusing.
As someone who grew up in a touristic area next to the sea, I can't help but feel close to "summery" and "maritime" themes. But to combine that with an object-head? That's a surefire way to make me like something.
A combination that's tropical storm-proof!