He then played a supporting role in Ram Gopal Varma's Rann, again co-starring Amitabh Bachchan, Paresh Rawal and Rajpal Yadav.
In 2009, his first release was Aladin, co-starring Amitabh Bachchan, Sanjay Dutt and Jacqueline Fernandez. 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. He appeared in the comedy Dhamaal which was a semi hit. Later that year, he appeared in Sajid Khan's directorial debut Heyy Babyy, co-starring Akshay Kumar and Fardeen Khan, which was a huge hit. He was seen in guest roles in Ram Gopal Varma's Darna Zaroori Hai, and then Namastey London, which was a box office hit. He appeared in Malamaal Weekly and Apna Sapna Money Money apart from Bluffmaster! with Abhishek Bachchan in the lead. Ritesh, by now had earned a strong foothold in the Bollywood film industry via his comic roles. While the film was reviled by critics, it was appreciated by audiences and declared a moderate success at the box office. His first relatively successful lead role occurred in the widely panned sex-comedy Kyaa Kool Hai Hum with Tusshar Kapoor. He subsequently appeared Bardaasht and Naach, both of them being box-office duds. He gained fame after his performance in Masti, which earned him two minor awards. Regardless, the film performed well at the box office. In his third film, Masti, a comic thriller, his role was widely disparaged. Riteish made his Hindi film debut with the 2003 romance, Tujhe Meri Kasam opposite Genelia D'Souza. The following year, he made his acting debut in Marathi cinema with the action film Lai Bhaari (2014).
Apart from Hindi films, Deshmukh has made his debut as a film producer with the Marathi success Balak Palak (2013). His highest-grossing releases came with the thriller Ek Villain (2014) and the comedy films Housefull (2010), Housefull 2 (2012), Grand Masti (2013), Housefull 3 (2016), Total Dhamaal (2019), Housefull 4 (2019) and Marjaavaan (2019). Subsequently, he starred in several commercially successful comedies including Masti (2004), Kya Kool Hai Hum (2005), Bluffmaster! (2005), Malamaal Weekly (2006), Heyy Babyy (2007), Dhamaal (2007) and Double Dhamaal (2011). Īfter making his acting debut with the 2003 drama Tujhe Meri Kasam, Deshmukh gained praise for his performance in the 2004 comedy Masti. He was ranked third in The Times of India's Top 20 Most Desirable Men of Maharashtra in 2018. Riteish Vilasrao Deshmukh (born 17 December 1978) is an Indian actor, television presenter and film producer known for his work in Hindi cinema and Marathi cinema.