Shashi Kumar's first released film was Chiranjeevi Sudhakara starring Raghavendra Rajkumar. In 1989 he became popular with Yuddha Kaanda starring V. Ravichandran and Poonam Dhillon and acted in key roles in big films like C.B.I Shankar and Sangliayana 2. Two successful 1990 films Rani Maharani and Baare Nanna Muddina Rani established him as a top hero of Kannada cinema. Shashi Kumar and Malashri, who acted together in several hit films together are considered one among the all-time great pairs of Kannada cinema. He was also paired with other popular actresses like Sudha Rani, Tara, Soundarya and Sithara.