The Gentry Brothers Circus was developed by four Gentry brothers from Bloomington, Indiana and was probably the greatest dog and pony show ever developed in the United States. The brothers father was Richard Henry Gentry - number 202 in the 1909 book on the family. Richard Henry Gentry was born in Stokes County, North Carolina, September 23,
1825; moved to Indiana with his father William when he was a child, and later married Frances Umbarger. The children of this marriage were Wallace, Henry, William, Frank, Lillie, and Jesse. Henry B. (H.B.) Gentry was the moving force among the brothers.
1899: Bought the elephant Pinto.
1900: acts using humans and elephants were added to the program.
1902: the Gentry Brothers Circus switched from a car show setup to flat cars. Twenty baby elephants were purchased in this period which allowed a distribution of five for each of the units. An elaborate route book for 1902 was published which listed a total of 72 railroad cars, 22 elephants, 12 camels, 12 sacred cattle, and 50 big horses.
1910: the Gentry Brothers Circus was considered the largest traveling show in the U.S. It had 7 elephants and 4 camels.
1915: The Gentrys lost control of the show.
1916: the circus had new owners: Ben Austin and J. C. Newman, operating as Gentry Brothers Circus (Austin and Newman).
1922-23: James Patterson purchased the circus during the winter and operated it as the Gentry-Patterson Circus to 1925.