Gestures of pain along with synonyms of that word, like agony or despair, were frequently used in the history of art. The very first examples come from ancient times, and while we do encounter them again in the Romanesque era, the Gothic and Renaissance period are the ones that have an ample amount of them. That is why the Gothic period is so important, it created a boom that got these gestures back in style. Furthermore, it did so through Biblical themes. From Giotto to Donatello we can observe how figures free themselves and transform, letting their pain finally come to life. The figures by themselves using certain types of gestures, like pulling hair, prove to us their agony. These gestures are mostly those of “passionate pain” where they are shown in a form of self-harm, but certainly, there are those relatively stable too. Motives of traditional suffering, popular in the Romanesque period, can also be seen in this period, but with some change in the gesture and mostly with side characters. In this work we shall offer insight on the development of this freedom of figures in painful themes, accompanied with even more distressing gestures. The themes will be taken from the Holly Bible, since those are the most recurrent displays throughout the age, especially containing a considerable amount of this symbolism.