Every form of art bears tracks from the artist’s real or fictive experience. Physical pain as an important human experience have been discussed, described and painted in many literary works. In addition, there are enough proofs to believe that toothache – a unique representative of bodily pains- is an old friend of humanity. Hence, it is more than natural to see the reflections of this symptom in the written literature. In this essay we are going to focus on two particular literary works of different genres; a novella and a fairy tale: Dostoyevsky’s ‘Notes from Underground’ and Hans Christian Anderson’s ‘Aunty Toothache’. These two authors and these two particular works have been studied in many different aspects. However, the place and importance of the concept of ‘Toothache’ was not investigated in previous analyses. Therefore, the subject of this paper is justified in one hand, original and unprecedented on the other hand. As it shall be seen, Dostoyevsky uses toothache as a tool to attack the basics of ‘Rational Egoism’ in 19th Russia and employs it to counter-argument against natural and historical determinism in favor of human’s free will. In the case of Anderson, toothache is an allegory about friendship and art in which toothache accompanies, and is compared with the pain of striving to produce a piece of art.