Upbringing and education are notions that are intrinsic to human cognition and the entire human life. Throughout history, there was not a single period or place in time where human race was not raised and educated. Every human being must go through the educational and developmental system. A point could be made that these two notions are the very basis of the human species and what distinguishes them from other living beings. In this paper we shall deal with the notions of ubringing and education, and seek the best possible methods in which to raise and educate children. How shall we go about it? By summarising the work of the three giants in the field of philosophy of education - Plato, J. J. Rousseau and J. Dewey. We shall present the main guidelines of their approaches, and, thorugh a critical representation from contemporary perspective, provide a personal opinion on the important elements of upbringing and education. In the conclusion, we shall give an overall view of the topics discussed, where we shall demonstrate the viewpoint we personally advocate, and the standpoint which is currently the most common and the most suitable. In such a debate it is quite difficult to separate the pedagogical aspect from the aspect of the philosophy of education, so we shall focus on the positions expounded earlier, by the three giants of philosophy of education, concerning the proposed aspects. Therefore, their positions shall not be considered separately, within the overview of the questions concerning konwledge or ethics, as a typical philosophical overview would, but rather highlighted in the pedagogical domain.