His first released film was Chiranjeevi Sudhakara starring Raghavendra Rajkumar. He became popular by the movie Yuddha Kaanda in 1989 which starred V. Ravichandran and Poonam Dhillon. Later he starred in some unsuccessful films like Baa Nanna Preetisu, Gandharva and Kollura Kaala. The 1990 film Rani Maharani made him a successful star. Further, he went on to become one of the most sought after stars. Shashikumar, along with fellow South Indian actress Malashri, have been known as all-time greatest pairs in Kannada movies. Other actresses Sudha Rani, Tara and Shruti were also paired with him in many films.
He has also acted in many Tamil and Telugu films. The prominent one is Rajinikanth starrer Baasha.
At the peak of his acting career, he suffered a drunken-driving accident near the Bangalore Turf Club. Ensuing surgeries changed his looks. Consequently, he was no longer considered for leading roles with the huge banners. This also pushed him to take the plunge into politics. After a long gap, he has made a comeback to cinema and has acted in supporting roles in multi-starrer films like Yajamana, Habba and Yaarige Saluthe Sambala.