15 Best O. Henry Short Stories You Should Read

In the vast literary landscape of short story writing, few names shine as brightly as O. Henry. Born as William Sydney Porter in 1862 in Greensboro, North Carolina, he went on to adopt his famous pen name in tribute to his prison guard while serving time for alleged embezzlement. However, the shadows of his personal life never dimmed the luminescence of his literary contributions. Instead, his experiences added depth, humour, and a unique perspective to his tales, making them rich tapestries of life’s intricate play of fate, love, and irony.

O. Henry’s tales are more than just stories; they are windows into the human soul. They reflect the hopes, dilemmas, aspirations, and challenges faced by ordinary people, often set against the vibrant backdrop of bustling New York City or the quaint towns of early 20th-century America. His stories weren’t merely observations but celebrations of life, highlighting its ironies and coincidences. The beauty of an O. Henry narrative lies not just in its plot, but in its ability to capture the essence of an entire lifetime within the confines of a few pages. It’s a journey where the destination often surprises the reader, thanks to his legendary twist endings.

What sets O. Henry apart from other writers of his era—and indeed, many who came after him—is his keen sense of observation, coupled with a profound empathy for his characters. Be they love-struck couples, weary travellers, ambitious young women, or mischievous children, O. Henry painted each character with such warmth and detail that they leap off the pages, becoming living, breathing entities. This characteristic storytelling brilliance makes narrowing down his vast oeuvre to a mere fifteen stories a challenging task. However, the following list attempts to encapsulate the quintessence of his storytelling magic.

1. The Gift of the Magi

In “The Gift of the Magi,” readers are introduced to Della and Jim, who despite their financial challenges, yearn to gift each other something special for Christmas. Their story is a testament to the selfless lengths couples will go for one another. However, O. Henry’s narrative takes a poignant twist when the sacrifices they make render their gifts pointless, beautifully illustrating that true love’s worth is immeasurable.

2. The Ransom of Red Chief

In the amusing tale of “The Ransom of Red Chief,” Sam and Bill’s nefarious plan to kidnap a boy for ransom is turned on its head. The boy’s mischievous antics reveal that even the best-laid plans can go awry. O. Henry skillfully weaves humour and irony into this tale, hinting that life’s unpredictability is its only constant.

3. The Last Leaf

The Last Leaf” offers a heartrending glimpse into despair and hope. Johnsy’s fragile state of health and her symbolic association with the falling leaves captivate the reader’s emotions. The elderly artist Behrman’s sacrificial act serves as a beacon of hope and underscores the indomitable spirit of humanity in the face of adversity.

4. The Cop and the Anthem

The Cop and the Anthem” introduces us to Soapy, whose winter plight leads to numerous schemes to get arrested. Yet, every attempt yields unexpected results. When a profound moment of introspection strikes Soapy, fate offers another twist. O. Henry brilliantly juxtaposes humour and irony to comment on the capricious nature of life.

5. A Retrieved Reformation

Chronicling the journey of Jimmy Valentine in “A Retrieved Reformation,” O. Henry delves into themes of love, redemption, and second chances. As Jimmy endeavours to distance himself from his criminal past, he is faced with a moral crossroads that will define his future. The narrative stands as a testament to the idea that love can indeed pave the path to redemption.

6. After Twenty Years

The emotional tale of “After Twenty Years” hinges on the reunion of two friends, Bob and Jimmy. Their long-standing pact to reunite takes an unforeseen turn, thrusting them into a moral quandary. O. Henry brilliantly navigates the intricacies of loyalty and duty, showcasing that sometimes, the lines between right and wrong can blur.

7. The Duplicity of Hargraves

Set against the backdrop of financial struggles, “The Duplicity of Hargraves” brings forth the tale of Major Talbot and his unexpected saviour, Hargraves. Their interactions present a heartwarming tale of pride, honour, and the lengths one may go to preserve another’s dignity, demonstrating the profound impact of kindness and empathy.

8. The Furnished Room

The Furnished Room” is a haunting exploration of love, hope, and despair. As a young man searches the labyrinthine streets of New York for his lost love, he stumbles upon chilling revelations. O. Henry masterfully crafts an atmosphere of suspense and melancholy, shedding light on the ephemeral nature of life and love.

9. The Green Door

Venturing behind “The Green Door,” Rudolf Steiner’s life takes a serendipitous turn. His unexpected encounter with a young woman in distress reveals that sometimes, destiny lies in the unlikeliest of places. O. Henry’s narrative serves as a poignant reminder of life’s unpredictable charm and the magic of chance encounters.

10. The Clarion Call

In “The Clarion Call,” Detective Barney Woods is thrust into a riveting moral dilemma when his path crosses with an old acquaintance, Johnny Kernan. As past debts and present duties entangle, the narrative unravels the complexities of honour and ethics, demonstrating that every choice comes with its own set of consequences.

11. The Cactus

The Cactus” offers a deep dive into the world of misunderstandings and lost opportunities. As Trysdale grapples with the aftermath of a broken engagement, a simple cactus stands as a symbol of unspoken words. O. Henry highlights the fragile nature of relationships and the perils of miscommunication, urging readers to cherish and understand their loved ones.

12. Mammon and the Archer

Mammon and the Archer” is a rich tapestry of love, wealth, and destiny. As Anthony Rockwall attempts to manipulate circumstances using his fortune, he learns that the heart operates on its own whims. O. Henry beautifully conveys that while money can pave the way, genuine connections are made in the simplest of moments.

13. The Caballero’s Way

The enthralling narrative of “The Caballero’s Way” transports readers to the Texas-Mexico frontier, where passion and danger intermingle. The infamous ‘The Cisco Kid’ and his tumultuous romance with Tonia Perez unfold a tale of love, trust, and betrayals, reminding readers of love’s unpredictable nature.

14. The Skylight Room

Through the lens of “The Skylight Room,” O. Henry presents Miss Leeson’s dreams juxtaposed against stark realities. Her undying optimism in the face of adversity is both heartwarming and tragic. As her world darkens, a glimmer of hope shines through, underscoring the profound impact of unexpected kindness.

15. Conscience in Art

Conscience in Art” delves into the psyche of Tim Lacy, an artist torn between commercial success and artistic integrity. As he stands at the crossroads, the narrative offers a profound exploration of the constant tussle between conscience and compromise. O. Henry’s tale resonates with anyone who has ever grappled with maintaining authenticity in a commercial world.


O. Henry’s tales are more than just stories; they are a tapestry of human emotions, intricacies, and ironies. With each narrative, he painted vivid pictures of life’s complexities, always with a twist that left readers in contemplation. His stories, drawn from everyday encounters, carry universal truths that resonate even today. From tales of sacrificial love to profound moral dilemmas, each story serves as a reminder of the unpredictability of life and the enduring spirit of humanity.

O. Henry’s masterful storytelling, replete with wit and warmth, ensures that his legacy as one of the greatest short story writers remains undiminished. For readers, both old and new, his tales are an everlasting treasure, offering both entertainment and profound insights into the human heart.

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