Gentry began as a rural Ozark agricultural community named Orchard City. Located in Western Benton County, it was known for its apple orchards and other produce. The town began to grow when the Kansas City and Southern Railroad constructed a railroad through the town. In 1894, residents of the community petitioned the county to officially incorporate, and the city's name was changed to Gentry, after an official in charge of the construction of the railroad.
The railroad proved important to Gentry and by 1903 the town had grown to a population of 1,000.
The railroad company built a new depot in Gentry in 1926-1927. It was known as one of the nicest depots on the railway line. A banquet was held for the grand opening and railway officials arrived on a special train to commemorate the event. Four to six passenger trains a week came through Gentry until passenger service was discontinued in 1964.
In 1946, the City Council voted to buy a water tank for $1,650 from the War Assets Corporation in Kentucky. In 1948, the city held a special election to issue bonds to install larger water mains and additional fireplugs. In the 1950s, the city purchased its own water company. At the beginning of the 21st century, Gentry was expanding water lines into rural areas surrounding the community.
Using donations, local businesses built the first auditorium at the intersection of Main and Collins Streets. The building now houses the city's police department and courtroom.
In the 1960s, when agriculture was no longer the economic base it had once been for the city and the railroad, the train depot was torn down.
The next decade saw the beginning of the construction of a power plant by Southwestern Electric Power Company (often known as SWEPCO). The plant is a coal-fueled electric generating facility called Flint Creek Power Plant. Today SWEPCO continues to provide electrical power, and SWEPCO Lake is used for fishing and recreation. To ease traffic through down town, a new Arkansas Highway 12 bypass was built on the southern edge of town.
In 1983, the McKee Foods Corporation (then known as McKee Baking Company) opened its manufacturing facility in Gentry.
The city celebrated its centennial in 1994 and held a 110th Birthday Bash in 2004.
According to the United States Census Bureau, the city has a total area of 2.4 square miles (6.2 km²), all of it land.
There were 842 households out of which 35.6% had children under the age of 18 living with them, 54.6% were married couples living together, 13.8% had a female householder with no husband present, and 27.9% were non-families. 25.3% of all households were made up of individuals and 13.2% had someone living alone who was 65 years of age or older. The average household size was 2.57 and the average family size was 3.06.
In the city the population was spread out with 29.1% under the age of 18, 8.8% from 18 to 24, 29.0% from 25 to 44, 19.7% from 45 to 64, and 13.4% who were 65 years of age or older. The median age was 34 years. For every 100 females there were 90.4 males. For every 100 females age 18 and over, there were 83.9 males.
The median income for a household in the city was $31,765, and the median income for a family was $37,569. Males had a median income of $27,361 versus $20,875 for females. The per capita income for the city was $14,309. About 11.7% of families and 13.2% of the population were below the poverty line, including 15.0% of those under age 18 and 17.6% of those age 65 or over.
Gentry's largest employer is McKee Foods Corporation, maker of the famous Little Debbie and Sunbelt snacks. McKee foods celebrated 20 years of manufacturing in Gentry and dedicated a 40,000 square-foot expansion to the existing plant in 2002. The company thrift store is located on the corner of Arkansas Highway 59 and Main Street. Visitors come from about a 100-mile radius to take advantage of the discounted cookies and cakes.
Many small, family-operated businesses reside in Gentry as well, most notably Sullivan's Barber Shop and Pioneer Pizza.
Tufco Flooring is also based in Gentry. It was started back in the 60's by Paul, Donald, and Frank Cox. It now has franchises all over the U.S. with 3 in Gentry alone. Arkotex Inc., Tufco International, and Tufco Great Lakes. They are the industry leader in industrial flooring.