East St. Louis was named an All-America City in 1959, having retained prosperity through the decade as its population reached a peak of 82,295 residents. Through the 1950s and later, the city's musicians were an integral creative force in blues, rock and roll and jazz. Some left and achieved national recognition, like Ike and Tina Turner, and jazz great Miles Davis, who was born in nearby Alton and grew up in East St. Louis. Many were featured on the PBS series River of Song in 1999, covering music of cities along the Mississippi River.
The city was dramatically affected by mid-century deindustrialization and restructuring. As a number of local factories began to close because of changes in industry, the railroad and meatpacking industries also were cutting back and moving jobs out of the region. This led to a precipitous loss of working and middle-class jobs. The city's financial conditions deteriorated. Elected in 1951, Mayor Alvin Fields resorted to ill-judged funding procedures to try to buy the city out of its financial morass. The scheme increased the city's bonded indebtedness and the property tax rate. More businesses closed as workers left the area to seek jobs in other regions. Crime increased as a result of poverty and lack of opportunities. The city is also left with expensive clean-up of brownfields, areas with environmental contamination by heavy industry that makes redevelopment more difficult.
Street gangs such as the War Lords, Black Egyptians, 29th Street Stompers and Hustlers appeared in city neighborhoods. Like other cities with endemic problems by the 1960s, East St. Louis suffered riots in the latter part of the decade. In September 1967, rioting occurred in the city's South End. Also, in the summer of 1968, a still-unsolved series of sniping attacks took place. These events contributed to residential mistrust and adversely affected the downtown retail base and the city's income.
Construction of freeways and urban sprawl contributed to East St. Louis' decline as well. The freeways cut through and broke up existing neighborhoods and community networks. The freeways also made it easier for residents to commute back and forth from suburban homes, so more were inclined to move to newer housing. East St. Louis adopted a number of programs to try to reverse decline — the Model Cities program, the Concentrated Employment Program and Operation Breakthrough. The programs were not enough to offset the industrial restructuring.
In 1971, James Williams was elected as the city's first black mayor. Faced with overwhelming economic problems, he was unable to stop the city's decline and depopulation. By the election of Carl Officer as mayor (the youngest in the country at that time at age 25) in 1979, many said the city had nowhere to go but up, yet things grew worse. Middle-class whites and African Americans left the city. People who could get jobs simply went to where there was work and decent quality of life. Because the city had to cut back on maintenance, sewers failed and garbage pickup ceased. Police cars often did not work, and neither did their radios. The East St. Louis Fire Department went on strike in the 1970s.
Before Gordon Bush was elected mayor in 1991, the state imposed a financial advisory board to manage the city in exchange for a financial bailout. State legislative approval in 1990 of riverboat gambling and the installation of the Casino Queen riverboat casino provided the first new source of income for the city in nearly 30 years.
The past decade can be characterized as one of redevelopment and renewal. In 2001 the city completed a new library. It also built a new city hall. Public-private partnerships have resulted in a variety of new retail developments, housing initiatives, and the St. Louis Metrolink light rail, which have sparked renewal. Access to the Metrolink from the East Side has become a controversy in the Saint Louis Metro Area, as a 2008 article in the Riverfront Times stated that it has resulted in skyrocketing crime rates on the west side of the River in affluent suburbs. 
The city, now small in terms of population, is still one of the prime examples of drastic urban blight in the country. Sections of "urban prairie" can be found where vacant buildings were torn down and whole blocks became overgrown with vegetation. As East St. Louis has suffered from white flight and disinvestment for many years already, much of the territory surrounding the city remains undeveloped to this day, bypassed for growth in more affluent suburban areas. Thus, many old, "inner city" neighborhoods abut large swaths of corn and soybean fields or otherwise vacant land. In addition to agricultural uses, a number of truck stops, strip clubs, and other semi-rural businesses surround blighted areas in the city as well.