Bobay originally gained a following on Vine and was known for his Nailed It series on the app. Before Vine shut down, Bobay garnered more than 700,000 followers. He would move to other platforms and as of May 2018 he had 262k followers on Instagram, 166k followers on Twitter, and 279k subscribers on YouTube. He started his YouTube channel in February of 2014 and his video topics include reactions, music, vlogs, skits, and more. Bobay's most popular videos include "RECREATING CRINGY RELATIONSHIP MUSCIAL.LYS!!!", "REACTING TO F**K GIRL MUSICAL.LY (CRINGEY!)", "GIRLFRIEND DOES MY MAKEUP | Conner Bobay", "Storytime: I ATE A TAMPON *Not Clickbait*", and "Conner Bobay - 10 Racks (Official Music Video)."
Bobay started dating Karlee Steel in 2016 and they have a joint YouTube channel together that is named Karlee and Conner. Their videos include pranks (some of which involve bodily fluids) and vlogs. As of May 2018, they had over 1.4 million subscribers.