Social media A video of Rolling Ray negatively reviewing
Popeyes'
chicken sandwich in 2019, in which he called it a waste of his money and said, "It's not even giving what y'all said it was supposed to gave," went viral online and coined the popular online phrase "
it's giving". Rolling Ray also coined the term "purrr" in a 2020 YouTube video, a variation of the term "
period" which saw widespread usage as slang to express approval, particularly on
TikTok. By 2021, he had become popular through his
Instagram account, @iamrollingray, where he had more than 445 thousand followers by 2025. In 2019, Rolling Ray appeared on the "Harper vs. McCormick" episode of the court show
Divorce Court, then hosted by
Lynn Toler, with his high school boyfriend, Christian McCormick, whom he insulted in the episode as "really terrible". In 2022, Rolling Ray hosted and executive produced the
Zeus Network reality dating show
Bobby I Love You, Purrr, in which contestants competed to become media personality Bobby Lytes's boyfriend. Rolling Ray and Lytes had previously appeared in a 2021 episode of the Zeus Network series
The Conversation focused on a social media feud between them. Mike Therkelsen of
Instinct noted that the series was "the first gay dating show in a long time" by 2022. He modeled in
Telfar and
UGG's ad campaign for their Krinkle collaboration in October 2023. ==Personal life and public image==