Brown was born in Mineola, a small segregated town in east Texas marked by racial tensions, to Minnie Collins Boyd and Lewis Brown. Brown was the fourth of five children. During Brown's childhood, mob violence periodically erupted in Mineola, keeping African- Americans from voting. His first job was a shoeshine boy in a whites-only barber shop.

In 1995, Brown ran for Mayor of San Francisco. In his announcement speech, Brown said San Francisco needed a "resurrection" and that he would bring the "risk-taking leadership" the city needed. Brown placed first in the first round of voting, but because no candidate received 50 percent of the vote, he ran against incumbent Frank Jordan in the December runoff. Brown gained the support of Supervisor Roberta Achtenberg who had placed third in the first round of voting. Brown campaigned on working to address poverty and problems with Muni. He called Jordan the "inept bumbler" and criticized his leadership. Jordan criticized Brown for his relations with special interests during his time in the State Assembly. Brown easily defeated Jordan in the runoff.  Brown's inaugural celebration included an open invitation party with 10,000 attendees and local restaurants providing 10,000 meals to the homeless. President Bill Clinton called Brown to congratulate him, and the congratulations were broadcast to the crowd. He delivered his inaugural address without notes and led the orchestra in "Stars and Stripes Forever". He arrived at the event in a horse-drawn carriage. According to the New York Times, Brown was one of the nation's few liberal big city mayors when he was elected in 1996.  In 1996, more than two thirds of San Franciscans approved of Brown's job performance. As mayor, Brown made several appearances on national talk shows. Brown called for expansions to the San Francisco budget to provide for new employees and programs. In 1999, Brown proposed hiring 1,392 new city workers and proposed a second straight budget with a US$100 million surplus. He helped to oversee the settling of a two-day garbage strike in April 1997. During Brown's tenure, San Francisco's budget increased to US$5.2 billion and the city added 4,000 new employees. Brown tried to develop a plan for universal health care, but there wasn't enough in the budget to do so. Brown put in long days as mayor, scheduling days of solid meetings and, at times, conducting two meetings at the same time. Brown opened City Hall on Saturdays to answer questions. He would later claim of his mayorship that he helped restore the city's spirit and pride.  Brown's opponents in his 1999 mayoral reelection campaign were former Mayor Frank Jordan and Clint Reilly. They criticized Brown for spending the city's US$1 billion in budget growth without addressing the city's major problems and creating an environment in city hall of corruption and patronage. Tom Ammiano was a late write-in candidate and he faced Brown in the runoff election. Brown won reelection by a 20 percent margin. He was supported by most major developers and business interests. Ammiano campaigned on a promise that he would raise the minimum wage to US$11 per hour and scrutinize corporate business taxes. Brown repeatedly claimed that Ammiano would raise taxes. President Clinton recorded a telephone message on Brown's behalf. Brown's campaign spent US$3.1 million to Ammiano's US$300,000. The 1999 mayoral race was the subject of the documentary See How They Run.

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