Sukumar and Toleti began their career as writers in Telugu cinema and worked as writers for a few films. After writing three scenes for Jayanth C. Paranjee's Bavagaru Bagunnara? (1998), they were summoned by the college to help them in recruiting students. They walked out of the film on moral grounds. Due to lack of earnings, Sukumar briefly continued to teach students, earned money, and returned to film industry. He worked as an assistant director for Manasichi Choodu (1998). Sukumar later assisted Editor Mohan for Kshemamga Velli Labhamga Randi (2000) and Hanuman Junction (2001). Before making his directorial debut, Sukumar worked under V. V. Vinayak for Dil (2003) as an assistant director.
In most of his films, Sukumar's protagonists are shown to be characterised with grey shades. Y. Sunita Chowdary of The Hindu commented that Sukumar "revels in giving a slight twist to his protagonist, in his background and character" and leaves the audience to understand him as he "unties the knots during narration and justifies his behaviour and makes us root for him". Karthik Keramalu of CNN-IBN, in his review of Kumari 21F, stated that Sukumar's lead characters are "psychologically wired differently", adding that at least one of the characters in his films "behaves in a way that will amuse the audience and the other characters present in the film". Regarding the same, Sukumar said, "We all have a lot of emotions and we suppress most of them fearing rejection. Instead we sport a smile and move on in this world. Problems arise when we don't enjoy all feelings like jealousy, selfishness and don't express them. To achieve something, there must be a driving force and that could be jealousy which you term as negative".
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