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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.
The film received negative response from critics, though it performed well commercially. It proved a commercial hit despite being a shoestring budget.
He then starred in a sequel, Housefull 2, which released on 6 April 2012 and was a huge success like its predecessor.
Housefull 2 has been marked as Ritesh's biggest success to date.
Ritesh, by now had earned a strong foothold in the Bollywood film industry via his comic roles He appeared in Malamaal Weekly and Apna Sapna Money Money apart from Bluffmaster! He appeared in the comedy Dhamaal which was a semi hit.
(2005), Malamaal Weekly (2006), Heyy Babyy (2007), Dhamaal (2007), and Double Dhamaal (2011) – and achieved further success with starring roles in several top-grossing comedy films, including Housefull (2010), Housefull 2 (2012), Grand Masti (2013), and Housefull 3 (2016).
In 2014, Deshmukh received critical acclaim for his performance as a serial killer in the top-grossing thriller Ek Villain that earned him several awards and nominations.
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.