Part of a prominent family, he attended local schools. He went to West Point in 1833. Graduating in 1837, he ranked 18 out of 50 in his class. He fought in the Seminole War, then resigned from the service to become a lawyer and legislator in Rocky Mount, Virginia. While he voted against secession in the state convention of 1861, he chose to join the state forces in Lynchburg when
Virginia seceded, and was commissioned as a Colonel in the 24th Virginia.
After Virginia's official secession, Early joined his regiment in Manassas Junction. He commanded troops at Blackburn's Ford, then served under Brigadier Gen. P. G. T. Beauregard at the battle of 1st Bull Run. His actions at 1st Bull Run impressed his superiors so much that he was appointed a Brigadier General.
After taking part in the battle at Cold Harbor, he led his troops across the Potomac River and score a victory, probably the most important of his career, at Monocacy. Nevertheless, Early's operation there alerted Union forces in the Washington area, forcing Early to abandon his plans to attack the capital. Along his retreat, he took part in the burning of Chambersburg, in revenge for the Union's destruction of the Shenandoah Valley. Early went on to lead troops against Major Gen. Philip H. Sheridan at Fisher's Hill, Winchester, Cedar Creek, and Waynesborough.
After the Confederacy surrendered, Early traveled to Texas in disguise, then went to Havana, Cuba and Toronto, Canada. While in Canada, he wrote "A Memoir of the Last Year of the War" in 1867, then returned to Lynchburg in 1869 and resumed his law practice. He refused to accept the Confederate defeat graciously, unlike many of his Confederate colleagues.
Later in life, he supervised the Louisiana State Lottery, and was the first president of the Southern Historical Society. He revised his memoir and published it as "Autobiographical Sketches" in 1912, exhibiting his defiance toward reconstruction.
During the war, Early was a profane and cantankerous fighter.