Dow Jones Industrial Average
1896-20091929 Wall Street Crash
1930's Great Depression
1950-1960's Post-WWII Baby Boomer Generation
1973 and 1979 Oil Crisis and Stagflation
1987 Black Monday
2000-2002 Dot-com Bubble Collapse
2007-2009 Global Financial Crisis
1995-2000 Dot-com Bubble
1930's Great Depression

The Dow Jones fell from a high of 386.10 on 3rd September 1929 to a low of 40.56 on July 8th 1932, a massive nominal drop of 89.5% and 87.5% inflation-adjusted. The market would not recover to nominal 1929 prices again until the 1950's, some 25 years later. In inflation-adjusted terms, the market price of an average investment made in 1929 would not break-even again until 1960, some 31 years later.