Beggars On Horseback is an evocative novel that was originally published in 1924. The book describes the social commentaries and superficiality of the Jazz Age which is mostly termed as the post-World War and majorly known for its dynamic culture, and changes in overgenerous life. The story of the book describes the narrative of a protagonist who is quite a talented and struggling artist amazingly known for his romantic interest towards Pamela Thursby. Along with this, the novel assists in exploring the themes of materialism and invidious conflicts between art and commerce people who have been facing moral dilemmas and changes in society. The book Beggars on Horseback describes gentle pursuit to metaphor suggesting artistic creativity and social status. The characters grapple in the novel to make choices in a world of finances and creating integrity appears to be odd. Jesse offers a commentary on the effects of putting material achievement before artistic passion by combining drama, humour, and symbolism to analyse the values of the day. The book, which perfectly captures the spirit and paradoxes of the Roaring Twenties, is regarded as a classic of social satire.