Rachael and comedian Ry Doon, drink cocktails and chat about everything from the life of a comic, how Ry became one of the biggest Vine stars and the one time that he got recognized by a homeless man. Ry discusses how he started in the business, how he developed his crazy arsenal of characters. Ry first became well known for his Jay-Z impressions as well as Vines where he creates pandemonium on the streets of Boston. He posted his first couple of Vines on February 21, 2013, a month after the app was introduced. He would become one of the earliest, most successful personalities on the app. He surpassed the 3.4 million followers on Vine.