Two modern commentaries on Kohelet (Ecclesiastes) take radically different approaches to illuminating this challenging biblical text's existential wrestling with faith and meaning. Fox's JPS Commentary emerges as the more accomplished work, masterfully balancing scholarly analysis with spiritual accessibility through its parallel presentation of Hebrew text and New JPS Translation, enriched by classical rabbinic interpretations. Through comparative analysis of the commentaries' interpretive approaches, organizational structures, and intended audiences, this review reveals how Fox's treatment proves superior in unpacking Kohelet's internal logic and philosophical development. While the Kravitz-Olitzky volume offers valuable contemporary Jewish perspectives and inspirational "Gleanings," its verse-by-verse format fragments the text's argumentative flow. Fox's commentary ultimately succeeds by helping both scholars and general readers navigate Kohelet's profound exploration of divine inscrutability and life's injustices while maintaining faith - offering a model for modern spiritual seekers facing doubt and uncertainty. The comparative methodology demonstrates how organizational choices and interpretive frameworks critically impact readers' ability to engage with this ancient text's enduring questions about meaning, justice, and belief.