This is a really interesting topic to me, because I've felt a pull toward things like this myself and seen it for decades. For example, the top of the README in my Zephyros project[1] was very playfully done, and very well received too.

People are naturally more lighthearted and organic than the sterile software and documentation we tend to write, and we're more social too, wanting to connect with others even if it means through a simple in-joke or catch phrase.

[1] https://github.com/sdegutis/zephyros