In the "Roaring Twenties", Wall Street was experiencing a Bull Market, where stocks just continue to rise based on optimism and investor confidence. Most of these stocks that continued to rise were over-valued, which caused the market to drop and crash. This crash not only caused many to lose money, but it caused America to lose hope, seeing past the facade of economic prosperity.
Many who had invested in the stock market in the 1920's were blinded by the false prosperity of the time, thinking that they could make it big if they invested money that they did not really have. Though only 1.5 million of 120 million Americans were investors, the crash greatly impacted the American psyche, crushing hopes and dreams for prosperity. The economic turmoil caused by this great financial loss ushered in the Great Depression, and would go down in history for that reason.
This political cartoon represents the Stock Market Crash of 1929. The roller coaster represents the Bull Market. The drop off along with the little bit of remaining supplies is symbolic of the crash, for the businesses were so optimistic regarding the extravagance of their roller coaster, but they lacked the resources to make their expectations a reality. The man waving his hand and talking is the businesses, explaining the crash to the investors, who is represented by the man staring up at the unfinished coaster. The title speaks truth, for throughout the "Roaring Twenties", the stock market led people on quite the ride, until it came to a crashing halt in 1929.