Academically trained, Clark first attended University of the South in Sewanee, Tenn., on a Wilkens Scholarship, the highest academic honor awarded to incoming students. The prerequisite art courses were waived due to the level of work he demonstrated upon entry into the college. Clark managed senior level courses as a freshman and was into his independent studies at the end of his first year. He finished his Bachelor's of Fine Art degree at Florida Atlantic University in Boca Raton.

Since elementary school he drew horses. Clark’s love affair with horses began at an early age growing up in San Diego. Around the time Bobby was 10 years old his family moved to a 200-acre cattle farm in Henry, Tenn. More interested in playing baseball than rural living, the move proved to be a tough transition for the young Clark, but once the family picked up a horse, country living improved dramatically.

For an artist who had received awards in every juried gallery show entered, it was a humbling experience when in 1984 at his first selling show in Louisville, Kentucky; he took 30 pastels of horses and brought all but one home. The state tax collector looked at his one lonely receipt and waived the sales tax saying, “Kentucky can get by without the $6.”

During the same Kentucky trip, Clark headed to Lexington in hopes of being able to photograph the champion horses of esteemed Claiborne Farms. Seabiscuit was born at Claiborne where 6 of the 11 Triple Crown winners were conceived. Over the phone, Clark was informed by the farm that they no longer allowed artists to use their horses as models. He still made the pilgrammage to Lexington. Almost by accident, he happened upon Claiborne and gathered his portfolio and some courage; Bob walked in to present his artwork. The farm manager gave Clark's work a rave review and ordered a private photography session with the horses including: Secretariat, Spectacular Bid, Mr. Prospector, Conquistador Cielo, Tom Rolfe, Riva Ridge, Nijinsky II. Bob was then directed to the old Spendthrift Farm to photograph Seattle Slew and Affirmed.