- He belongs to a family of political lineage with Indian National Congress, as his father, Late Vilasrao Deshmukh, served as the Chief Minister of Maharashtra, twice. His brothers are also associated with the Indian National Congress and he also is a loyal campaigner of the same party.
- He is a qualified architect and started his career in the same field in New York City.
- His perfect comic timing in the adult comedy ‘Masti’ (2004) established him as an actor.
- His first film in a villainous role was Sidharth Malhotra and Shraddha Kapoor starrer ‘Ek Villain’ (2014), for which he grabbed many awards.
- He has designed the interiors of the office premises of Shah Rukh Khan’s production house ‘Red Chillies Entertainment’, and Karan Johar‘s house at Union Park (Bandra).
- He loves number 1 so much that all his cars have the number 1.
- He appeared in the comedy Dhamaal which was a half-hit.
Deshmukh began his film career with the 2003 novel, Tujhe Meri Kasam, opposite Genelia D'Souza. Later, he appeared in Out of Control, which reported a relatively moderate performance. In his third film, Masti, a comic thriller, his role has been widely disparaged. Regardless, the film performed well at the box office. He became famous after his performance at Masti, which earned him two minor prizes.
He later appeared Bardaasht and Naach, both of whom missed out on the box office. Her first relatively successful lead role was in the Kyaa Kool Hai Hum sex comedy with Tusshar Kapoor. While the film was criticized by critics, it was appreciated by the public and reported moderate success at the box office. Ritesh now has a strong presence in the Bollywood film industry thanks to its comic roles
He appeared in Malamaal Weekly and Apna Sapna Money Money outside of Bluffmaster! with Abhishek Bachchan in the lead. He was seen in guest roles in Darna Zaroori Hai of Ram Gopal Varma, and then Namastey London, which was a box office success. In 2007, Cash followed. Later that year, he appeared in Sajid Khan's first film, Heyy Babyy, with Akshay Kumar and Fardeen Khan, which was a huge success .
In 2008, he played a leading role in De Taali, in which his performance was praised, and later in Chamku, both of which had poor box office results.
Deshmukhwith co-stars Jacqueline Fernandez and Amitabh Bachchan , in 2009.
In 2009, his first release was Aladin, with Amitabh Bachchan, Sanjay Dutt and Jacqueline Fernandez. He was in the multi-starcast, Aladin. He then played a supporting role in Rann's Ram Gopal Varma, again with Amitabh Bachchan, Paresh Rawal and Rajpal Yadav. His last film of 2009 was Do Knot Disturb with Govinda, Sushmita Sen, Sohail Khan and Lara Dutta.
In 2010, he worked with Sajid Khan on Housefull comedy with Akshay Kumar, Deepika Padukone, Lara Dutta, Arjun Rampal and Jiah Khan. The film received a negative response from critics, although it did well on a commercial level. His first release of 2011 was F.A.L.T.U., in which he played the role of Bajirao, a fake college director. His second release of the year was the comic double Dhamaal. Both were above average sizes and very successful.
In 2012, he appeared for the first time in Tere Naal Love Ho Gaya in which he is paired up against his real wife Genelia D'Souza. It has proven to be a commercial success despite a limited budget. He then plays in a suite, Housefull 2, released on April 6, 2012 and is a huge success as its predecessor. Housefull 2 has been marked as the most successful Ritesh to date.