In August 2015 Hollywood was featured on the BBC genealogy documentary series Who Do You Think You Are? The programme revealed that his grandfather Norman Harman, who served in the Army during World War II, saw action in the Tunisia Campaign and at the Battle of Anzio and that his great-great-grandfather, Kenneth MacKenzie, had been a policeman in the City of Glasgow Police in the 1850s. Hollywood's great-great-great-grandfather, Donald MacKenzie, had been a crofter in Poolewe, Wester Ross. Donald had also been the post-runner between Poolewe and Dingwall, where he delivered post on foot over a distance of 60 miles (97 km). He covered this distance every week, during his forties, on foot for over a decade. He lived into his 80s.
In 2015 Hollywood began his racing career, making his debut in the Beechdean AMR Aston Martin Vantage GT4 with Andrew Howard, founder of Beechdean Dairies. The pair qualified second in the Britcar Trophy Championship's first round at Silverstone taking second in class in both races. He also competed at Le Mans in 2015 in the Aston Martin festival. Hollywood has also competed in GT Cup with Jonny Adam and finished first in class. He entered the British GT championship in 2016 and competed in the last three rounds with Jamie Chadwick as his driving partner. In July 2017 he came first in class at the Dunlop endurance race at Silverstone in an Aston Martin GT4, and in November 2017 he raced in his first 24 hr race at Circuit of the Americas coming second in class in an Aston Martin GT8.