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Man, why are there so many Kuroko's Basketball specials? Unlike the more popular DVD specials, Kuroko's Basketball: An Idiot Can't Win came with the 25th volume of the manga but adapts a story from the 5th volume. So we have a weird case where the special takes place way earlier in the chronology than where the actual anime series was.
The Seirin High basketball team is in trouble: ace player Kagami is so incredibly stupid that he's at risk for placing in the bottom 100 of the preliminary exam participants. But the preliminary exams don't actually affect grades. The problem? Students in the bottom 100 are forced to take a weekend study course that's conveniently scheduled during the inter-high basketball championships.
Thus begins the arduous task of getting a student who averages like 10% to be a top 200 student. The whole Seirin team volunteers to help tutor Kagami because they know they'll need him in the upcoming matches. Meanwhile, short scenes show Kise and Midorima's own problems with the practice exams.
So, as you can imagine this special doesn't elaborate on important relationships or past history like Tip Off or Can We Do That One More Time?. It's more of a comedy/slice of life thing, but the story premise is too shallow to be worthy of a full-sized episode. Primarily because the actual progression of the plot is obvious and redundant. Kagami's dumb and keeps failing at questions his teammates ask him, but we already know partially due to the time this was released and common sense that he overcomes it all in the end just in time. A lot of the same gags stretched out through the whole thing, character details we aren't interested in like which academic subject each one specializes in, and nothing relevant to the main storyline. Nothing likely to make you appreciate it more either. Seirin's team support helps Kagami pass but it's the main theme beaten down throughout the whole series in more substantial ways.
I really don't recommend this to anyone but the hardcore fans most desperate for any additional Kuroko's Basketball. It's not an embarrassingly humored watch or even that boring, just totally unnecessary. You'd need a very high attachment to the characters to appreciate it any more than that, and if you ask me the characters weren't a strong suit of the series. If you want to watch this, I recommend at least watching it when it takes place chronologically (after the match with Midorima), since that'll probably make it feel slightly more important to the overarching storyline. That'll make it an easier watch and some decent downtime between the next match.