Born Webb Parmelee Hollenbeck, Webb was born in Indianapolis, Indiana. According to city directories of the period, all of Jacob and Mabel Hollenbeck's residences were in the heart of Indianapolis. In 1886 and 1887, Jacob G. Hollenbeck was at 40 Windsor Block. In 1888, he resided at 135 E. Vermont Street. In 1889 and 1890, Jacob and Mable lived at 305 N. Mississippi Street. In 1891, they lived at 74 W. New York Street. In 1892 and 1893, they lived at 229 N. Pennsylvania Street. Webb was the only child of Jacob Grant Hollenbeck (1867 – May 2, 1939), the ticket-clerk son of a grocer from an Indiana farming family, and his wife, the former Mabel A. Parmelee (aka "Parmalee" or "Parmallee"; March 24, 1869 – October 17, 1960), the daughter of David Parmelee, a railroad conductor. The couple married in Kankakee, Illinois on January 18, 1888, and separated in 1891, shortly after their son's birth. According to Marion County, Indiana, Marriage Records, they married in Indianapolis on January 18, 1888. According to Illinois State Archives, they married on January 1, 1889.
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