Pictures can expose gaps in representations. Painters sometimes playfully use these gaps to bridge and reveal ideas about what we cannot see. Gaps can offer a space for imagination, encouraging the viewer to create mental images and ignite pictorial innovations. Hell, purgatory, heaven, and life on earth (as well as in between these temporalities) are sometimes all represented in one picture, e.g. in the Coronation of the Virgin by Enguerrand Quarton (1453) or the Triptych of St. John the Baptist and John the Evangelist by Hans Memling (1479). Presenting these disparate temporalities in one space relies, in these works, on gaps. Images related to realms in the mind of the beholder of these pictures may close such gaps through imagination or expand them with thoughts and reflections. The surviving contracts and documents between patrons and painters are very explicit, yet they remain curiously silent regarding aspects of representation. Digging deeper into another kind of gaps, those linking images, imagination, and representational systems, will allow us to understand how late medieval painters paved the ground towards the early modern era.