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Bobby Simha was born in Hyderabad, Andhra Pradesh and then brought up in Kodaikanal and notes that he considers the latter as his native place. He subsequently completed his schooling there and then attended college in Coimbatore. In 2005, he participated in a Coimbatore-based event called Naalaya Natchathiram, where chief guests Sundar C and E. Ramadoss suggested that he should attempt to become an actor in Tamil films. Simha stated that he received an offer to feature in a TV serial in Chennai and only after making the journey from Coimbatore, did he realise he had been conned. Simha subsequently finished his degree and came back to Chennai to pursue a career in acting but ended up working in different industries including marketing, insurance and business process outsourcing to fulfil his financial needs. He subsequently got acquainted with short film maker Manikandan, who introduced him to his friend, another short film-maker Karthik Subbaraj. The pair subsequently made a series of short films together, with Subbaraj giving Simha a role in his directorial debut Pizza, too. Balaji Mohan, who too was short film-maker, gave Simha a small role in his first feature film, Kadhalil Sodhappuvadhu Yeppadi. Both ventures became critically acclaimed and amongst the most profitable of 2012.

Simha then appeared in Soodhu Kavvum (2013) portraying the role of Pagalavan, and played the antagonist in the bilingual Neram, his performances in both films were received well. In 2014, he was seen in the role of an ageing Madurai gangster in Jigarthanda  with his portrayal winning him critical praise. In an interview he said that in order to get into the character, he had interacted with real gangsters to learn their behaviour and nuances. To tan his skin, he stood in the sun at noon wearing only his shorts. The film opened to positive reviews in August 2014, with The Hindu writing that it had achieved "cult status" within a week of its release. Simha won positive reviews for his depiction of Sethu, with Rediff.com noting that Simha "steals the show. He is chillingly menacing at times, while completely hilarious in others, but equally convincing in both", stating it is "a truly remarkable performance". A critic from Sify.com delivered a similar verdict, writing "truly the film belongs to Simhaa. He is electrifying especially in the first half, where he brings out the viciousness and violent streak of the character along with that eerie laughter." After Jigarthanda he played a lead role in the Malayalam film Beware of Dogs, while in Aadama Jaichomada he played Bhoominathan, a "serious, intelligent cop but with a comic touch". Simha's upcoming films, the anthology horror film Aaaah, the action-thriller Urumeen  and Karthik Subburaj's next Iraivi, will all feature him in lead roles.