this would definitely be the way to attract more lurkers, especially younger ones.
i hate the y2k shite as much as the next guy but right now (if not last year) is the perfect time to act on something like this as internet culture nostalgia amongst youngsters seems to be at an all time high.
people are more willing than ever to learn about the older ways and integrate themselves into it.

My stylistic suggestion would be to have a quick, easily sharable, eye-catching animation like the first video you linked followed by a cute oekaki drawing, akin to the infamous Heyuri-tan Dreaming Vidlii ad, to play the songs over.