No large cities are located in the Bootheel. Sizable towns include Kennett, the birthplace of singers Sheryl Crow, David Nail, and Trent Tomlinson; and Sikeston, the birthplace of professional athletes James Wilder Sr., Brandon Barnes, and Blake DeWitt. Sikeston's city limits fall within both Scott County and New Madrid County. Cape Girardeau and Poplar Bluff are often considered to be part of the Bootheel due to the influence the two cities have had on the development of the region, but neither is located within its geographic boundaries.