During the period known as the ‘Phoney War,’ the comedic song ‘The Biggest Aspidistra in the World’ became a significant cultural reference point in the UK, along with its singer, the renowned Gracie Fields. This was a notable achievement given the shifting public tastes within the country during a period of widespread uncertainty and transformation. However, despite the song’s wartime popularity, it has received little scholarly attention. This paper traces the rise and fall of ‘The Biggest Aspidistra’ in the UK during the Phoney War, exploring its impact through an analysis of the national symbols in its lyrics, its comedic delivery by Fields, and its collaborative musical approach. By bridging musicology and cultural history, this paper clarifies the importance of comprehensive song analysis to Second World War studies and underscores the role of humour in bolstering wartime morale.