In 2022, rapper Jack Harlow approached Churchill Downs three weeks before the Kentucky Derby and asked to film a video for his collaboration with Drake, “Churchill Downs,” on Derby day. He was named Grand Marshal of the event, brought both Drake and influencer Druski with him, filmed the video during the race and was carried across the track to avoid dirtying his shoes.
According to Ramage, the Derby’s TikTok following increased 700% after Harlow’s appearance, inspiring the Derby to focus on its TikTok and Instagram presence each year since. It also helped it focus on its ties to fashion, inviting more designers to the race and creating the Derby’s first style guide with journalist Zanna Roberts Rassi and partners including Vineyard Vines, Longines, Radley London and Brackish.