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A fantastic show in terms of both entertainment value and listening practice. Shirokuma Cafe manages to be extremely funny while also being very laid back and relaxing. The whole vibe is a lot more subtle than most comedy but clever wit and steady stream of gradually building running gags and character bits makes for some real laugh-out-loud moments (the panda family's stage play at the zoo is one of the most unhinged, hilarious moments in the entire series).
As far as language goes, this is a bit trickier than Teasing Master Takagi-San, but still very approachable. I was surprised I got some of the more fast paced rants and I'd say with the japanese subtitles on I probably got about 90% of what they were saying. As I approached the last quarter or so I did find my eyes leaving the subtitles a bit more frequently which is promising. One of the running gags is Shirokuma's love of dajare, a type of gag where someone says a word, and Shirokuma starts pulling out objects that vaguely rhyme with the word. I already had a familiarity with this type of gag from reading Super Mario-Kun so I knew what the bit was, but I had about a 50% success rate guessing the word (though it is kind of the in-universe point that the other characters also have to guess the word, so it's supposed to be a challenge). Those scenes are always a fun little brain-teaser. The only bits I completely failed to comprehend were the little post-credit stingers which tended to not only be very fast but also complete non-sequiturs so you don't really have as much context to go off of. I think there were maybe two I got without having to stop and pause.
The actual stories and characters are also great. It's sort of a chill hangout show where nothing important really happens, the humor just comes from the gradually growing cast of characters all interacting with and opining on various topics. My favorite has to be Penugin, he has the funniest voice and the most character growth. At the start of the show he seems like the straight man, but we gradually learn of his various quirks and eccentricities, from his chaotic dating life to his Squidward-esque taste in pretentious art. Every scene with Penguin is a treasure.
The other characters are a ton of fun, with their various oddities gradually coming to light. As the series progresses, the cast expands and each new addition is another great addition to the recipe. I particularly loved all the extra penguins, from the trio who tries to sell educational playing cards to the cute baby penguins who run around making train noises. You get the feeling that the show's world really is alive and seeing different characters cross paths and have their own little adventures and backstories really makes it all feel fleshed out.
Overall an extremely charming show and I'm actually sad it's over because it feels like the kind of thing where you could have twice as many episodes without it ever getting stale. I've heard the manga has a fairly different set of stories so I imagine I'll be reading that in the not too distant future to get more Shirokuma goodness.