Winnie-the-Pooh, the beloved bear created by A.A. Milne, marked his 100th anniversary this October, an occasion marked by widespread recognition including a week of programming on BBC Radio 4, a set of Royal Mail postage stamps, and a commemorative Google Doodle. First published in 1926 and illustrated by E.H. Shepard, the character quickly became a cultural icon, selling 150,000 copies in the United States alone within its initial months.

Despite its enduring popularity, Winnie-the-Pooh’s legacy is complex. Milne himself expressed ambivalence, feeling the character overshadowed his work as a playwright and humorist. His son, Christopher Robin Milne, who inspired the stories, later described the bear as having interfered with his own childhood. The character has also faced literary criticism for being overly sentimental; notable authors such as P.G. Wodehouse and Evelyn Waugh were less than impressed. Nonetheless, children's affection for Pooh has never waned—he was ranked seventh in a 2003 public poll to identify the nation’s favorite book character.

Pooh’s status as Britain's quintessential bear faces competition from Michael Bond’s Paddington Bear, introduced 32 years later in 1958. Both characters emerged in the wake of major wars, with Pooh representing an escapist retreat from the First World War’s devastation and Paddington inspired by the experiences of evacuees during the Second World War. While Pooh inhabits the tranquil Hundred Acre Wood, Paddington’s story unfolds amid the bustling environment of London’s Paddington Station. The bears have both been embraced by the British royal family; however, Paddington was notably invited to tea during Queen Elizabeth II’s platinum jubilee celebrations, reflecting his association with more contemporary Britain.

Paddington’s cultural relevance has been enhanced by three successful films and a popular stage musical, casting him as a symbol of modern British values. In contrast, Winnie-the-Pooh is often seen as emblematic of a more genteel, nostalgic past. The bear’s presence in popular culture has been varied: Disney’s 1966 animated adaptation drew criticism from Shepard, who deemed it a “complete travesty,” and more recently, Pooh has appeared in unexpected contexts such as the 2023 indie horror film "Winnie the Pooh: Blood and Honey."

Pooh has also assumed a unique political role in China, where President Xi Jinping has been compared visually to the bear since 2013, sparking protests in Hong Kong that adopted Pooh symbolism to express dissent. Additionally, a Canadian medical journal proposed that many of Milne’s characters represent different mental health conditions—Tigger as ADHD, Piglet as anxiety, and Eeyore as depression—though the article may have been partly tongue-in-cheek. Author Matt Haig has described Winnie-the-Pooh as “the ultimate self-help book,” highlighting the enduring comfort the stories provide amid the pressures of modern life. The simple, whimsical world Milne created remains a source of solace, where a boy and his bear can continue to play undisturbed.