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Best books by Shashi Tharoor

22nd Sep 2025
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Shashi Tharoor is a literary titan, a voice that resonates with sharp wit, profound intellect, and an unparalleled command of the English language. From searing critiques of colonial legacies to insightful explorations of Indian identity and the intricacies of global politics, his literary output is as diverse as it is impactful. Whether delving into historical narratives, crafting compelling fiction, or dissecting contemporary issues with an unflinching gaze, Tharoor's books offer readers a rich tapestry of thought-provoking prose and unforgettable characters. This list celebrates the very best of his remarkable literary journey, highlighting works that have captivated, challenged, and inspired countless readers. Now, it's your turn to weigh in! Shashi Tharoor's bibliography is extensive and beloved, and we want to know which of his literary achievements stand out most for you. Explore the titles presented here, reminisce about your favorite reads, and cast your vote for the books that you believe best represent his genius. Your selections will shape the ultimate ranking, creating a definitive guide to the Shashi Tharoor books that have left the most indelible mark on your literary landscape.

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Best books by Shashi Tharoor

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#12.

The Five Dollar Smile and Other Stories

12/16
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Shashi Tharoor's **The Five Dollar Smile and Other Stories** is a compelling testament to his multifaceted literary talent. This collection, marked by both poignant emotional depth and sharp wit, demonstrates Tharoor's mastery in exploring the human condition across a spectrum of relatable experiences. From the universal ache of longing in the title story, where a young Indian orphan's journey to America mirrors the anxieties of any child, to the playful, Wodehouse-inspired "How Bobby Chatterjee Turned to Drink," Tharoor seamlessly blends cultural observation with accessible narratives. The inclusion of stories reminiscent of O. Henry and Maupassant, such as "The Temple Thief" and "The Political Murder," further highlights his skill in crafting engaging plots with unexpected turns, while the college tales offer a delightful glimpse into youthful exuberance and burgeoning intellectualism. This collection firmly earns its place on a list of Shashi Tharoor's best books due to its demonstration of his foundational writing prowess and the early emergence of themes that would define his later acclaimed work. **The Five Dollar Smile and Other Stories** showcases not only his "daunting literary acumen" but also the "keen sensitivity" that allows him to tackle complex subjects like family conflict and mortality with both profound insight and entertaining flair. The self-aware humor found in "The Solitude of the Short-Story Writer," with its Woody Allen-esque introspection, reveals an early aptitude for nuanced character studies and thematic exploration, proving that even in his earlier writings, Tharoor was already a formidable voice capable of moving and engaging readers on multiple levels.
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#12.

The Five Dollar Smile and Other Stories

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Shashi Tharoor's **The Five Dollar Smile and Other Stories** is a compelling testament to his multifaceted literary talent. This collection, marked by both poignant emotional depth and sharp wit, demonstrates Tharoor's mastery in exploring the human condition across a spectrum of relatable experiences. From the universal ache of longing in the title story, where a young Indian orphan's journey to America mirrors the anxieties of any child, to the playful, Wodehouse-inspired "How Bobby Chatterjee Turned to Drink," Tharoor seamlessly blends cultural observation with accessible narratives. The inclusion of stories reminiscent of O. Henry and Maupassant, such as "The Temple Thief" and "The Political Murder," further highlights his skill in crafting engaging plots with unexpected turns, while the college tales offer a delightful glimpse into youthful exuberance and burgeoning intellectualism. This collection firmly earns its place on a list of Shashi Tharoor's best books due to its demonstration of his foundational writing prowess and the early emergence of themes that would define his later acclaimed work. **The Five Dollar Smile and Other Stories** showcases not only his "daunting literary acumen" but also the "keen sensitivity" that allows him to tackle complex subjects like family conflict and mortality with both profound insight and entertaining flair. The self-aware humor found in "The Solitude of the Short-Story Writer," with its Woody Allen-esque introspection, reveals an early aptitude for nuanced character studies and thematic exploration, proving that even in his earlier writings, Tharoor was already a formidable voice capable of moving and engaging readers on multiple levels.

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