Edward D. Gentry was born in October 1865 in Kansas or Indian Territory to Eli Gentry (1841–?) and his wife Lucy (1842–?). His parents were termed "mulatto" in Census records and "colored" in Denison City Directories.

In Edward's teen years, his father operated a saloon on South Austin Avenue, organized a black minstrel touring group, had frequent brushes with the law, and participated in lodge activities in the African American community. Edward's mother Lucy was a laundress or stayed home raising the children. In January 1880, the family mourned the death of a small child.

In 1887, the Denison City Directory listed Edward as a barber at Thompson & Lott, operated by two African Americans, Joseph Thompson and Sylvester Lott. This business, billed as “barbers, shop and bath rooms,” occupied space at 104 West Main Street. This was the heart of the action around the Union Depot.

In 1891, Edward was a barber with Eugene Lafon at 111 East Main Street. He was rooming with another "colored" barber, Jesse A. Coleman. Jesse's barber shop shared a location at 209 South Austin Avenue with Eli Gentry's nightclub.

In 1891, Edward married Susie, a black woman born in October 1862 in Tennessee. In October 1892, they would have a daughter, Bernice.

Five years later, Edward had his own barber shop at 109 East Main Street, close to the Union Depot and in a prime location to catch travelers tired after loading commodities onto trains or emerging at their destination after long train rides. Working the barber shop with Edward was another African-American barber, James S. Love.

Edward continued to upgrade his enterprise, which was located on the second floor above other businesses and offered hot baths in addition to shaves and haircuts. The 1898-1899 City Directory called it the Palace Barber Shop, and Eddie's former employer, Sylvester Lott, worked there, as did Peter Williams and Sherley O. Platt. At this time, Edward Gentry and his wife had taken up residence at 627 West Bond Street. Platt lived a block away at 527 West Bond.

Through 1905, Edward remained at the same location and lived at the same address. Then he moved his business to 107 West Main in 1907. Around this time, the interior of his shop was featured in Industrial Denison, a high-quality pictorial book advertising Denison's most impressive homes and businesses.

Eddie passed away on July 14, 1908, and was buried in Denison's Oakwood Cemetery. As a fixture in downtown since his childhood, he seems to have been a great favorite of town leaders, who helped his surviving wife and daughter.

As the widowed mother of a school-age daughter, Susie took in laundry. But by 1911, she had the prestigious position of matron at the Union Station. Bernice completed her education and by 1913 had become a teacher at Anderson School, the African-American school near her home. The two women continued to live at 627 West Bond.