It was once a railway town and had long been a center of cotton culture, which is still an important commodity crop in the rural area.

It was once considered the second-largest city in Washington County in 1920 due to its rapid growth of residents, businesses, and schools.

[4] Other agricultural companies in the area are Lauren Farms BASF Stoneville Cotton, Bayer Crops Science, GreenPoint Ag, Azlin Seed Service, Corteva Agriscience, Pettiet Agricultural Services, Inc., Nutrien Ag Solutions, K-I Chemical U.S.A., Greenland Planting Company, Ayers-Delta Implement, Edward's Flying Service, Essie Patterson Farm Trucking, and Southern Seed Association.

Leland is the burial place of the folk artist and blues musician James "Son" Thomas, who lived for many years near the railroad tracks.

Zion Memorial Fund, to which musician John Fogerty of Creedence Clearwater Revival was a yearly contributor.

[10] The community is the childhood home of puppeteer Jim Henson, who was born in nearby Greenville, but raised in Leland.

[13] The territory that the town was built on was first settled on in 1834 by Samuel and Susan Jones, Mary Neely, and Malinda Breeland.

There was even a drawbridge that wad built by Leland settlers to be more closely connected with the people of Stoneville.

[14] Years later, the Buckner and Connerly families moved away and sold their land to Judge James Ruckus and William Yerger.

In 1869, their heirs quit claimed the land for release mortgages which passed to the hands of the Bank of Kentucky.

After seven years, Mississippi native Captain James Alexander Ventress Feltus (1840–1908) bought the 900 acres of land for $12,000.

[14] Captain James A. V. Feltus built his home at the “Three Oaks” and deeded a 100-foot right-of-way on the land to the Memphis and Vicksburg Railroad Company; however, no railway was built until 1885, when the right of way was given to the Louisville, New Orleans and Texas Railroad Company.

Leland was one of two cities considered for a terminus of several railroad lines, most notably, the Louisville, New Orleans & Texas Railway.

[14][16] It would seem that both accounts state that both men asked Captain Feltus to name the town in her honor.

[18][19] As the town continued to progress, it established its first newspaper publication, The Leland Record,[20] and businesses were established, including retail, banks, law firms, other railway companies, grocers, innkeepers, landlords and more.

In the scene, the three escaping convicts try to jump aboard a freight train only to fail and catch a handcar driven by a blind old man who makes wild predictions about their future.