There is a tendency for people to dislike successful individuals which is why we like to root for the underdog in many stories. If there are no obstacles for a character to overcome then there is a high chance for the narrative to feel stale. Haven't you Heard? I'm Sakamoto completely turns the underdog trope on its head by having a main character who can get out of any situation he finds himself in no matter what. I think what makes this work is the overall kindhearted nature of Sakamoto and the complete lack of seriousness in tone.
Sakamoto is the most popular student in high school and no matter what situation he finds himself in he always comes out on top. Of course, this makes him extremely popular with all the girls in his school and the boys hate him with a fiery passion. The way that Sakamoto solves problems is where the show is genius since it's always in a surprising and off-the-wall stylish manner. Some punks wanna dump a bucket of water on him while he using the bathroom? Well, too bad because he just so happens to have an umbrella on him. Someone stole his desk in his classroom? He lounges on the windowsill with the wind blowing through his hair and cherry blossom petals falling around him. You just can't beat Sakamoto, he's playing chess while these guys are playing checkers.
This series is only thirteen episodes, and to be honest, this concept would wear thin if it was any longer. The main meat of the series is how everyone else around Sakamoto takes inspiration from his optimistic outlook on life. He makes people want to be better and improve themselves. Even if they are consumed with jealously at first, they can't help but admire his resourcefulness and tenacity. For the most part, the tone is lighthearted but there are a few episodes that deal with a specific character that makes the stakes a bit higher. I found it to be slightly jarring, but the resolution ends up being just as hilarious as the rest of the show and even a bit poignant.
The animation from Studio Deen is average, but the character designs are great. It has a clean look to it and for some scenes they up the quality (mostly towards the end of the season). Yasuhiko Fukuda's compositions for the score are excellent--especially Sakamoto's theme that has a fantastic jazz/funk fusion sound to it. I also really dig the OP and the theme song Coolest by Customi-Z.
Haven't You Heard? I'm Sakamoto isn't your normal anime series but it's a super fun diversion from other generic high school shows. It definitely comes highly recommended.
-Michelle Kisner