Vail Pittman was educated by private tutors and in the public schools until he attended Sewanee Military Academy.

He then attended the University of the South and Brown's Business College, but returned to Lake Providence in 1903 to manage the family cotton plantation after Vail Montgomery's death.

He sold the coal business in 1907, and subsequently engaged in a variety of occupations, including undersheriff of Nye County, sergeant-at-arms of the Nevada Senate, and partner in a mining company.

[3] Pittman was also involved in several civic and business organizations, including the good roads movement and the local chamber of commerce.

After his brother Key's 1940 death, Vail Pittman unsuccessfully sought the governor's appointment to his U.S. Senate seat.