At age 17, Volodymyr Zelenskyy joined the local KVN, a comedy competition team and was soon invited to join the United Ukrainian team, Zaporizhia-kryvyi Rih-Transit which performed in the KVN’s major league and eventually won in 1997.
That same year, he created and headed the Kvartal 95 team which later transformed into the comedy outfit Kvartal 95. From 1998 to 2003, Kvartal 95 performed in the major league and the highest open Ukrainian league of KVN, the team members spent a lot of the time in Moscow and constantly toured around post-soviet countries.
In 2008, Zelenskyy starred in the feature film, Love in the Big City, and its sequel, Love in the Big City 2. Zelenskyy continued his movie career with the film, Office Romance. He was also a member of the board and the general producer of the TV channel Inter from 2010 to 2012.