Publisher Tim Keck (b. 1967) started the paper with the proceeds from the sale of an alternative paper in Madison, Wisconsin, and with a loan from his mother. Early circulation was disappointing, but when Keck began covering the cultural scene on Capitol Hill, the paper took off. The success of The Stranger was a major factor in The Weekly moving to free distribution in 1995.
By 1998, 60,000 copies of The Stranger were being distributed each week.