Mama says to Walter, "You ain’t satisfied or proud of nothing we done. I mean that you had a home . . . that you don’t have to ride to work on the back of nobody’s streetcar." Is Walter’s life likely to have been better materially or politically than his parents’s?

Reading or viewing A Raisin in the Sun from the perspective of the 21st century, we have the advantage of knowing what changes occurred in the United States since the mid 1940s–late 1950s, when the play is set. Lorraine Hansberry wrote it in 1958. Walter Younger, Jr., is 35 years old in the play, so he was already an adult when many of those changes happened. One interesting aspect of Hansberry’s play is that the characters do not neatly fit into generations. Beneatha is 15 years younger than her brother, and there are clear differences between them. In many ways, she has more in common with her nephew, who is only 10 years younger than she is.
While many of the major advances of the Civil Rights Movement happened in the 1960s, they did not come out of a void. In her mention of no longer sitting in the back of the streetcar, Mama is referring to the many boycotts held in the 1950s, most notably the Montgomery, Alabama bus boycott of 1956. The landmark US Supreme Court decision in Brown v. Board of Education, officially ending school segregation, came in 1954. Particularly relevant to the play’s events, as Lena purchases a home in a white neighborhood, are the changes in laws about housing segregation. Years before he argued for Brown before the Supreme Court, attorney Thurgood Marshall was one of the attorneys who successfully argued against covenants, which permitted segregation, such as in the 1948 landmark case of Shelley v. Kraemer.
The social changes that came more slowly than legal changes would affect people Walter’s and Ruth’s age, as well his sister and his and Ruth’s children. Many barriers to employment and social relationships, including interracial marriage, persisted, but attitudes were changing.
Massive participation in the Civil Rights Movement incorporated people of all ages. Martin Luther King, Jr., born in 1929, would be about Ruth’s age, while Representative John Lewis, born in 1940, who was Chairman of the Student Non-Violent Coordinating Committee during the early 1960s, would be about Beneatha’s age. College students like her played major roles in the Freedom Rides and the Summer of Freedom actions for voting rights. A huge number of demonstrations and marches occurred between 1962 and 1965; many claim the August March on Washington was the culmination of those efforts. Travis, age 10 in the play, would be graduating high school and registering for the draft eight years later, and he would most likely serve in Vietnam. And the new baby would be only a year or two older than future president Barack Obama, Jr., born in 1961.
https://www.history.com/topics/civil-rights-movement/naacp