Subsequent success and acclaim (2014–present)
Deshmukh started 2014 with a triple role in comedy Humshakals, opposite Bipasha Basu. The film failed at the box office and received negative reviews from critics. Following this, he played a serial killer in the thriller Ek Villain, opposite Aamna Sharif. The film was a box office success and the ninth highest-grossing film of the year and earned him the IIFA Award for Best Supporting Actor. Rajeev Masand stated that Deshmukh springs a surprise and was appreciative of him delivering a "compelling performance". Sweta Kaushal opined that he "steals the show with a stellar performance". He then expanded to Marathi films with Lai Bhaari. and then did a cameo in Entertainment. Lai Bhaari saw him play twin brother and emerged as the seventh highest grossing Marathi film ever. Mihir Bhanage found Deshmukh's Marathi debut "simply astounding".
Deshmukh's only release in 2015, was Bangistan, which was a commercial failure. He started 2016 with the sequel Housefull 3, where he played a car racer opposite Lisa Haydon. It became the seventh highest-grossing film of the year. After two cameos in Kyaa Kool Hain Hum 3 and Mastizaade, he appeared in another sequel Great Grand Masti opposite Puja Banerjee. Unlike the prequels, it failed at box office. His last release of the year was Banjo opposite Nargis Fakhri, where he played a local goon and band member. Tatsam Mukherjee found him to be "pretty entertaining".
Deshmukh then appeared in the 2017 film Bank Chor opposite Rhea Chakraborty, which was a commercial failure. In 2018, he first appeared as himself in Welcome to New York. He then played twin brothers in his second Marathi film Mauli opposite Saiyami Kher. Nandini Ramnath of Scroll.in stated, "Deshmukh, an affable presence whatever the role, is a stretch in the action sequences." It was a box office success.
Deshmukh had two commercial successes in 2019, which broke his box office failure since Housefull 3. He first appeared in the comedy sequel Total Dhamaal, which became a box office success. Ronak Kotecha was appreciative of his comic timing and character. He then played dual characters, one of a classical dancer and other a modern boy in Housefull 4 opposite Pooja Hegde and Kriti Kharbanda. It later became the seventh highest-grossing film of the year and Deshmukh's highest grosser till date.
Later the year, Deshmukh played a dwarf goon in Marjaavaan, which became an average grosser and had a cameo in Dream Girl.
Deshmukh had only one release in 2020, in Baaghi 3, where he played a fearful police officer opposite Ankita Lokhande. Despite mixed reviews, it became the second highest-grossing film of the year.
Deshmukh firstly had two cameos in 2022, in Ek Villain Returns and Marathi film Adrushya. This was followed by two streaming films, Plan A Plan B opposite Tamannaah Bhatia, and Mister Mummy opposite Genelia D'Souza. While Mister Mummy received negative reviews, for Plan A Plan B, Archika Khurana took note of Deshmukh's portrayal of the "cynical character". Deshmukh then reunited with D'Souza for the Marathi film Ved, also his debut as a director. He played an ex-cricketer forcibly married to his neighbour and later coaches his ex-lover's daughter. A commercial success, it became the fourth highest-grossing Marathi film of all time. Mayur Sanap opined: "From grief and anger, to frustration and cynicism, Riteish expresses a gamut of emotions in a fine performance." He earned a nomination for Filmfare Award for Best Actor – Marathi.
With no film release in 2023, Deshmukh started 2024 with Kakuda opposite Sonakshi Sinha, playing a ghost hunter. Deepa Gahlot noted, "Riteish plays Victor with such relish that without him, the film would have deflated quickly." He then played a pilot opposite Priya Bapat in Visfot. Devesh Sharma of Filmfare stated, "Deshmukh adds significant depth to Akash, skillfully conveying both vulnerability and inner conflict." These two films were followed by his streaming series debut, with Pill. Deshmukh played a man fighting corruption in Pharma industry. Shubhra Gupta was appreciative of his ordinary man portrayal that made the series engaging.
Deshmukh started 2025 with Raid 2, where he played a corrupt politician. Saibal Chatterjee was appreciative of his "solid performance", but criticised the character. The film was a commercial success at the box office. Deshmukh next played one of the primary character in Housefull 5 opposite Sonam Bajwa and Nargis Fakhri. The film was released in two versions, titled Housefull 5A and Housefull 5B, each featuring a different climax and murderer. Rishabh Suri opined that he "anchors" the film but is let down by weak writing. A commercial success, it emerged as one of the highest-grossing film of the year. In his final release of the year, Deshmukh appeared in the sequel Mastiii 4.
In 2026, Deshmukh directed and act in the Marathi–Hindi bilingual Raja Shivaji, which emerged as the highest-grossing Marathi film of all time. He also has Dhamaal 4 in the pipeline.
