EDIT: I added a shadow under the characters, because, you know, only freaks don't cast shadows in late-afternoon lighting conditions.

Original vector sketch by :iconc-quel::iconc-quel::iconc-quel::iconc-quel: and can be found here [link]

I only did the shading and some slight vector sketch modifications... anyhow, the characters represented here are the old Microsoft family circa 1985. Left to right we have:
-baby Windows 1.0-chan
-1.0-chan's older sister, MSDOS-tan
-Xenix-sama, who's some kind of assassin/caretaker
-And finally, MSDOS-tan's twin sister, PCDOS-tan

Background by =Fairiegoodmother [link]