He starred further in several commercially successful films including Nandhi (2002), Kiccha (2003), Swathi Muthu (2003), My Autograph (2006), No 73, Shanthi Nivasa (2007), Mussanjemaatu (2008), Ee Shathamaanada Veera Madakari (2009), Just Maath Maathalli (2010), Vishnuvardhana (2011), Kempe Gowda (2011), the Telugu-Tamil bilingual Eega (2012), Maanikya (2014), Ranna (2015), Kotigobba 2 (2016), Hebbuli (2017), The Villain (2018), Pailwaan (2019), Telugu-Hindi bilingual Rakta Charitra and the Hindi film Dabangg 3 (2019).

[7] He won the Filmfare Award for Best Actor – Kannada for three consecutive years for his films Huchcha, Nandhi and Swathi Muthu.

Sudeepa made his debut in Telugu cinema in 2012, with S. S. Rajamouli's Eega, a fantasy film in which he portrayed an industrialist who, on falling for an NGO worker (played by Samantha Ruth Prabhu), kills her alleged lover, who begins to haunt him in the form of a housefly.

[14] He frequently sings in his screen roles, including Vaalee (2001), Chandu (2002), Ranga SSLC (2004), Nalla (2004), #73, Shaanthi Nivaasa (2007), Ee Shathamaanada Veera Madakari (2009), Kempe Gowda (2011), Bachchan (2013)[15] and also for others movies such as Mandya to Mumbai (2014), Ring Road Shubha (2014) and Raate (2015).

In 2019, Sudeepa was seen in the Hindi film Dabangg 3 where he played the archenemy of Salman Khan's Chulbul Pandey.

From then he has directed many Kannada films like No 73, Shanthi Nivasa, Ee Shathamaanada Veera Madakari, Just Maath Maathalli, Kempe Gowda and Maanikya.

[19] He owns a film production company named Kiccha Creations, which is credited with My Autograph (2006), No 73, Shantinivasa (2007), Jigarthanda (2016), Maanikya (2013), Ambi Ning Vayassayto (2019).

He was roped in to play the main host of the reality show Pyate Hudgeer-Halli Lifu, aired on Suvarna,[21][22] which was an immediate success.

[40] In 2014, he was appointed as the Brand Ambassador for Intex Technologies (India) Mobiles & Paragon Footwear.

[41] In 2013, on World AIDS Day, Sudeepa teamed up with Vijay Raghavendra and other actors to record voiceovers for the TeachAids interactive software, developed at Stanford University.

[44] In 2022, he was appointed brand ambassador of Karnataka Animal Husbandry Department's cow adoption programme.

[45] On 13 June 2021, Sudeep along with Sajid Nadiadwala and Nikhil Kamath, Chief Information Officer and co-founder of Zerodha, cheated during the online charity event against five-time world chess champion Vishwanathan Anand.

[48][49] On 6 April 2023, at a press conference held in Ashok Hotel, Bangalore, Sudeepa openly declared his support for the then incumbent Chief Minister Basavaraj Bommai and the BJP in the 2023 Karnataka assembly elections.