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A short but effective summarizing article on the work and life of Schopenhauer, the Columbia Encyclopedia's entry is a concise yet effective start to exploring the figure, perfect for someone with no familiarity. The article describes Schopenhauer's early life, his early essays, important works, and the basic thesis of his philosophy, though with little depth as to be expected from a more general encyclopedia.

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Schopenhauer, Arthur. (2018). In The Columbia encyclopedia. (Eighth edition.). Columbia University Press. https://search.credoreference.com/articles/Qm9va0FydGljbGU6NjA4NTQ5

A more extensive and specialized reference entry on Schopenhauer, the Stanford Encyclopedia is a good place to dive deeper without having to rush headlong into primary texts or more robust guides/companions. The website, by and large, is a more specialized digital encyclopedia dedicated to philosophy specifically and Schopenhauer's entry goes into many of the same pieces as the Columbia Encyclopedia but with greater depth, rigor, and heavy citations.

Stanford Encyclopedia of Philosophy

Wicks, R. (2024). Arthur schopenhauer. In E. N. Zalta & U. Nodelman (Eds.), The Stanford Encyclopedia of Philosophy (Spring 2024). Metaphysics Research Lab, Stanford University.
https://plato.stanford.edu/archives/spr2024/entries/schopenhauer/

Another Stanford Encyclopedia entry, this one on Immanuel Kant. Although not on Schopenhauer directly, Kant is best understood as Schopenhauer's immediate predecessor and principle influence. At minimum, Schopenhauer considered himself in the tradition of Kant, and although his philosophy is very much distinct, gaining  a strong familiarity with Kantian metaphysics is essential for understanding Schopenhauer's ideas. The Stanford Encyclopedia entry should serve as a good entry point for exploring Kant's metaphysics without immediately being overwhelmed by the Critique of Pure Reason. His entry contains similar information to Schopenhauer's own - biographical, philosophical, and contextual.

Stanford Encyclopedia of Philosophy

Rohlf, M. (2024). Immanuel kant. In E. N. Zalta & U. Nodelman (Eds.), The Stanford Encyclopedia of Philosophy (Fall 2024). Metaphysics Research Lab, Stanford University. https://plato.stanford.edu/archives/fall2024/entries/kant/

The first of our more dedicated introductory texts and by far the shortest, Julian Young is a generally regarded as a strong scholar on continental philosophy, the philosophical umbrella in which Schopenhauer generally falls. Schopenhauer acts as a comprehensive summary of the eponymous figure, primarily focusing on Schopenhauer's philosophical content, covering similar points to the Stanford Encyclopedia entry but with yet greater depth and a different, more unified perspective. 

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Young, J. (2005). Schopenhauer. Routledge.

The most singularly robust introduction/companion text on this list, the Cambridge Companion is a hefty text that dives still yet deeper into Schopenhauer's philosophical ideas. The text is divided into sections each focused on a specific aspect of Schopenhauer's philosophical thought and written by a different scholar. This would be an excellent text to gauge what specific aspects of Schopenhauer's ideas you want to engage with whether it be his notion of the Will, his understanding of the self, his ethics, his relationship to Indian philosophical thought, or his relationship with prior, contemporary, and subsequent philosophers. Furthermore, the text has an extensive dedicated bibliography and index to further act as a more definitive resource.

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Janaway, C. (Ed.). (2009). The Cambridge companion to Schopenhauer. Cambridge University Press. (Original work published 1999)

A text focused on Schopenhauer's seminal work the World as Will and Representation, Robert Wicks' introduction to the text is perfect primer for a notoriously long and dense work. For someone who is principally interested in Schopenhauer's most famous book, this is a piece of prerequisite or, at minimum, contemporaneous reading. Whereas the introductory texts provide a more broad-level lens at Schopenhauer the figure or larger ideas that may be found across multiple of his works, Wicks' book is restricted to examining the singular, eponymous text.

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Wicks, R. (2011). Schopenhauer’s The world as will and representation: A reader’s guide. Continuum.

The only primarily biographical work on this list, Schopenhauer and the Wild Years of Philosophy should give a very robust account of Schopenhauer's personal life while working on his philosophical content. It spells out his relationship with contemporaries, his familial connections, and in general provides a rich narrative context with which to understand his philosophy from a new angle. Furthermore, the Safranski goes a long way in depicting the world and culture that Schopenhauer exists within, something that might be easy to overlook or forget for a modern reader.

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Safranski, R. (1991). Schopenhauer and the wild years of philosophy (1. Aufl). Harvard University Press.

One of the few primary texts on the list not written by Schopenhauer himself, the Critique of Pure Reason is the principal metaphysical work of Immanuel Kant, a German philosopher of the 18th century famous for his deontology and metaphysical system known as "Transcendental Idealism." The Critique centers on the latter, sketching out a full schema for Kant's own metaphysics which Schopenhauer would build upon. The Critique of Pure Reason is considered by Schopenhauer himself to be an essential text to understand before moving into his own philosophy since his own philosophical notion of the Will is built off Kantian ideas and distinctions which are first laid out in this book. The text is notoriously dense and difficult to read, structured along two different editions often packaged together, and so the Stanford Encyclopedia entry on Kant is highly recommended to prepare the reader at least on a basic level.

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Kant, I. (2009). The critique of pure reason (15th printing). Cambridge University Press.

Wilhelm Halbfass was a scholar primarily interested in Indian philosophy, and his main book India and Europe details the history of contact between Indian philosophical and religious ideas and European thinkers from antiquity into modernity. Given Schopenhauer's admitted interest in Indian religion and philosophy - most prominently the Upanishads - India and Europe goes a long way in describing the context in which Schopenhauer came across Indian philosophical/religious ideas, and thus, how specifically they might influence his own intellectual work.

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Halbfass, W. (1988). India and Europe: An essay in understanding. State University of New York Press.

The first of Schopenhauer's own writings on the list and a work that began as his doctoral dissertation before its later revision, On the Fourfold Root of the Principle of Sufficient Reason is considered by Schopenhauer himself to be foundational to properly and robustly understanding the rest of his philosophical corpus. The text itself focuses on the titular "principle of sufficient reason" which is the idea that all things muts have a sufficient reason or cause for existing; every entity, event, proposition, and so forth must have an explanation. The "Fourfold Root" refers to what Schopenhauer believes as the four principal manifestations of this idea and is an idea essential to fully understanding his metaphysics as described in subsequent works like the World as Will and Representation.

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Schopenhauer, A. (1997). On the fourfold root of the principle of sufficient reason. Open Court. (Original work published 1974)

Generally regarded as Schopenhauer's seminal work, the World as Will and Representation is an extensive treatment of his metaphysics and general philosophical system. The most recent, expanded version of the work is published within 2 volumes, the first outlining Schopenhauer's system of thought as it concerns everything from epistemology to ontology to aesthetics, and ethics whereas the second volume acts as a supplement to the first, meant to expand and clarify upon the ideas developed therein. The book, as to be expected of a primary philosophical text, is dense and requires strong familiarity with Kant's Critique of Pure Reason and his earlier Fourfold Root while also benefiting from an understanding of the Upanishads and Plato.

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Schopenhauer, A. (1969). The world as will and representation (Vols. 1–2). Dover Publications.

A lesser essay of Schopenhauer's but one still interesting as it related to his greater system of philosophical thought. A short essay published in 1836, it primarily deals with  the confirmation - or at least what Schopenhauer considers to be the confirmation - of his philosophical system by empirical/scientific findings alongside other contemporary fields of study. The essay is interesting, thus, to see Schopenhauer's perspective on the relationship between other fields of knowledge and how it related to his own work.

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Schopenhauer, A. (2023). On the will in nature: An account of the corroborations received by the author’s philosophy since its first appearance from the empirical sciences (K. Hillebrand, Trans.; Second edition.). Rogue Scholar Press.

A collection of two essays in the field of ethics elaborating on Schopenhauer's view of morality. The two essays are focused on two primary topics in ethics: the question of free will/determinism and the question of the basis of moral action. Schopenhauer argues for free will's illusory nature and the determinism of action and argues for a metaphysical grounding of ethics in compassion.

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Schopenhauer, A. (2014). The two fundamental problems of ethics. Cambridge University Press. (Original work published 2009)

A short essay written toward the end of Nietzsche's career wherein Nietzsche reflects on his own time as a philosopher, especially looking back at his time as a young philosopher. Although named in honor of Schopenhauer, it is less directly related to his work or philosophy and more the way that Schopenhauer approached philosophy. In this essay we can see how Schopenhauer was influential on Nietzsche by implication on Nietzsche's self reflection; although Nietzsche considered his own philosophy to contrast as heavily with Schopenhauer as possible, he considers him an educator through his iconoclastic style.

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Nietzsche, F. W. (2014). Schopenhauer as educator: Friedrich Nietzsche’s third untimely meditation. (D. Pellerin, Trans.). Amazon Fulfillment.

A foundational text in Indian religion and philosophy originally authored in antiquity, this religious text covers a wide variety of topics including rites and rituals alongside more philosophical concepts like ontology and consciousness. Although there are over 108 Upanishads in total, the source provided only contains the most essential 13. Although less essential for understanding Schopenhauer's thoughts, the influences of the Upanishads and Indian philosophy in general is still relevant and a valuable angle to consider when studying the thinker, being among his own listed influences in the preface to the World as Will and Representation. 

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Mascaró, J. (Ed.). (1984). The Upanishads (Repr., 1. publ. 1965). Penguin Books.