The truth and reality are two fundamental philosophical concepts upon which pragmatists have specific and important discussions. This paper compares Peirce’s and James’s ideas – both of which have proposed theories that challenge traditional metaphysics - on these two fundamental concepts in order to answer two questions of (1) why James has a wider reputation, his thoughts are more pursued, and is also called the founder of pragmatism, while Peirce is the founder of Pragmatism; and (2) whether the two philosophers’ pragmatism in the theory of reality and truth has been able to free itself from metaphysical philosophy? To answer these questions, this paper addresses these two philosophers’ point of views toward the theory of the truth. Although, it seems that the two concepts of truth and reality have clear meanings, there is a difference of opinion among pragmatist philosophers. Therefore, investigating the meaning, types, criteria, and position of the truth and reality in pragmatism reflects these philosophers’ opinions on these two concepts and also, answers the research questions of this paper. To answer the research questions, this paper applied a qualitative method, used a desk study, reviewed previous studies on relevant topics, and applied analytical arguments and interpretations. This paper shows that pragmatism is based on the pragmatic maxim that Peirce wrote and James also accepted. The overall criterion of this maxim is the practical impact that are reflected in propositions, believes, and notions to evaluate their practical consequences. In their views, although there are some literal dissimilarities between different believes, they have the same practical impact and address the same matter. Thus, they made a link between the theory and practice.  However, their views on traditional metaphysics make a distinction between these two philosophers. Peirce considers the pragmatic maxim as a logical principle, connects it to the theory of meaning, and offers different criteria - such as correspodence, compatibility, coherence, and consensus of scientific community – for evaluating the truth. Therefore, he gives a social character to the truth and takes the traditional metaphysics away from his philosophy. James, however, ties it with the theory of the truth that make it incompatible with the traditional metaphysics and Pierce’s criteria. These characteristics put James’ pragmatism at the top of the later pragmatist thoughts. In addition, this article explains that although both, Peirce and James, proposed new and effective views on the truth and reality and relations between them and they challenged some of the principles of metaphysical philosophy. Therefore, they did not think outside the framework of metaphysical thinking, could not withdraw this position, and did not propose totally novel ideas.