While Chikkanna was a part of a television show on Udaya TV, he was noticed by actor Yash, after which he was offered his debut movie Kirataka in 2011. Although he was cast in supporting roles in Raja Huli (2013) and Adyaksha (2014), he won immense praise for his comedy performances, which helped him win the SIIMA Award for Best Comedian. Some of his other movies include Ranna (2015), Rathavara (2015), Sharpshooter (2015), Masterpiece (2015), Nanna Ninna Prema Kathe (2016), and Kotigobba 2 (2016). In 2017 Chikkanna was associated with hit movies like Raj Vishnu, Hebbuli, Raajakumara, Bangara S/O Bangaradamanushya, Sathyaharishchandra and Mufti. In director Naresh Kumar H.N`s comedy-drama, Raju Kannada Medium (2018), Chikkanna acted alongside Gurunandan, Ashika Ranganath, Achyuth Kumar and Avantika Shetty. Other acting credits include Dalapathi (2018), Amma I Love You (2018), Raambo 2 (2018), Odeya (2019) and French Biryani (2020). In 2021, he appeared in films like Pogaru, Roberrt and Krishna Talkies, a horror-thriller movie directed by Vijayanandha.