The trick is to do these things without coming off artificial. If Microsoft or Apple tried this, it would backfire, though Apple could do many things MS can't because of their known focus on the end user.
Memorable and authentic is a win. Memorable and fake is poison. Unmemorable is the dead pool.
The weird thing is that today I could far more easily believe Microsoft doing something like this than Apple. When I think of how present-day Apple conducts itself, I think of cleanliness and sterility all the way. Microsoft, on the other hand, has been trying to be a bit more "goofy" since around Windows 7.
Memorable and authentic is a win. Memorable and fake is poison. Unmemorable is the dead pool.