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He subsequently appeared Bardaasht and Naach, both of them being box-office duds.
His first relatively successful lead role occurred in the widely panned sex-comedy Kyaa Kool Hai Hum with Tusshar Kapoor.
He married Genelia D'Souza, his co-star from Tujhe Meri Kasam, Masti and Tere Naal Love Ho Gaya on 3 February 2012.He has an elder brother named Amit and a younger brother named Dheeraj, both of them politicians.Deshmukh studied at G D Somani Memorial School and earned an architectural degree from Kamla Raheja College of Architecture, Mumbai.In 2008, he played a lead role in De Taali, in which his performance was praised, and later in Chamku, both of which performed poorly at the box office.In 2009, his first release was Aladin, co-starring Amitabh Bachchan, Sanjay Dutt and Jacqueline Fernandez. He then played a supporting role in Ram Gopal Varma's Rann, again co-starring Amitabh Bachchan, Paresh Rawal and Rajpal Yadav. U., in which he played the role of Bajirao, a fake college principal.