It makes me wonder if Housei was very popular at school in his youth.
He was actually yeah. I'm in the process of trying to decipher some interviews he did which included these pics (trying to sort out my PC right now though). But from what I understand he said in the Kansai area, being the funny guy was admired. His school's annual festival would have a vote amongst students and he came first for 3 years. They coined a term for him "cuool" (kawakkoi or something like that), cute and cool put together (he laughs at it now). In the High School batsu he gets asked about his school days and mentions he had quite a few friends from the kendo club too. In some talk show, maybe Downtown DX, he said he was popular and I think he said he'd flirt by coyly kissing the back of his hand and glancing up at a girl (the girls on the talk show didn't appreciate it when he demonstrated though
After high school he started off in a duo which won a newcomer award, but his partner changed careers early on. Going solo he initially had a bit of an idol status with his "baby face" and such, he mentions that he received valentines chocolates from viewers. But as his comedy character gradually became more defined as the suberi-gei / hetare / aho (one who falls flat / loses / fool), he stopped getting valentines. In Japanese comedy I guess such a character is seen as a low rung on the ladder, it worried him a lot it seems until he got more confidence through rakugo. But Norman Wisdom described his comedy character Pitkin as "The Successful Failure" and Charlie Chaplin (who also played a bumbling fool) named him as a favourite. Lee Evans is also very popular and has a very frantic blundering style (e.g. pretending to turn up on the wrong stage and fumbling through the audience to get to the right one). I find such an act funny and endearing but they're all British comedians so maybe it's just my perspective.