Cheatham was born in Nashville, Tennessee on a plantation called Westover, which in its prime consisted of three thousand acres (12 km2).

His mother was descended from General James Robertson, the founder of Nashville and "father" of Middle Tennessee, who came from Virginia.

The Cheathams had been in middle Tennessee for two generations and become established as plantation owners, lawyers, doctors and mayors of the city.

In December, Cheatham and his division received the thanks of the Confederate Congress "for the desperate courage they exhibited in sustaining for several hours, and under most disadvantageous circumstances an attack by a force of the enemy greatly superior to their own, both in numbers and appointments; and for the skill and gallantry by which they converted what at first threatened so much disaster, into a triumphant victory."

Cheatham was promoted to major general, on March 10, 1862, and was appointed commander of the 2nd Division, First Corps, Army of Mississippi.

At the latter battle, Cheatham performed sluggishly, ordering piecemeal assaults; observers claimed he had been drinking heavily and was unable to command his units effectively.

They had five children together: Benjamin Franklin Jr., Patton Robertson, Joseph Johnston, Medora Cheatham Hodgson, and Alice.

During his tenure in the latter position, he supervised landscaping improvements to Arlington National Cemetery, including restoration of the Lee Mansion and the building of the Tomb of the Unknowns.

He was an unsuccessful candidate for the United States House of Representatives in Tennesse's 1872 at-large congressional district special election, in which former President Andrew Johnson, after seeing that the Democratic nomination for the district would likely go to Cheatham, ran as an independent, throwing the election to Republican Horace Maynard.