[3] In his teens and early twenties, Kapoor developed obesity and approximately weighed 140 kg; he later said that due to his condition, he used to be "sloppy, grumpy" and "under-confident".

Later, he signed on to debut with the company's romantic drama Ishaqzaade (2012) opposite Parineeti Chopra, which tells the love story between a son and daughter of a Hindu and Muslim political family, respectively.

[16] While filming a running sequence for the feature in Barabanki, Kapoor suffered a spasm in his hamstring muscle, though he finished the scene after resting for five minutes.

Marking the directorial debut of Atul Sabharwal, it co-starred Prithviraj Sukumaran, Jackie Shroff, Rishi Kapoor and Amrita Singh; he portrayed two estranged twin brothers, Ajay and Vishal, who end up in each other's places as part of a huge conspiracy to overthrow their biological father's empire.

Saurabh Dwivedi stated that Kapoor "shows his pain through body language but falls short in some scenes opposite his co-actor Ronit Roy."

[23] His last release of 2014 was Homi Adajania's adventurous satire Finding Fanny, which co-starred Deepika Padukone, Naseeruddin Shah, Dimple Kapadia, and Pankaj Kapur and the movie follows the lives of five dysfunctional people in search of a titular woman.

[24] In 2015, Kapoor featured in his father's second younger brother Sanjay's first production Tevar, a remake of the Telugu film Okkadu (2003), in which he co-starred alongside Sonakshi Sinha and Manoj Bajpayee as a Kabaddi player.

[26] In 2016, Kapoor served as the host for the seventh season of Colors TV's reality stunts-performing series Fear Factor: Khatron Ke Khiladi.

[27] In the same year, he starred opposite Kareena Kapoor Khan in R. Balki's satirical comedy-drama Ki & Ka, based on the content of gender stereotypes.

Writing for India Today, Ananya Bhattacharya gave the film a negative review and wrote that Kapoor "looks like a mouthing sharp".

[29] The Mohit Suri-directed teen romantic drama Half Girlfriend was Kapoor's first film appearance of 2017, which served as a retelling of Bhagat's novel of the same name.

In 2018, Kapoor starred in a spin-off to the romantic comedy Namastey London (2007), named Namaste England, helmed by Vipul Amrutlal Shah.

"[32] 2019 to 2023 proved to be disappointing years in Kapoor's career, as these films he starred in were major commercial failures, except his OTT releases.

In 2019, his first release, the crime drama India's Most Wanted directed by Raj Kumar Gupta, he essayed the role of an agent who is given a secret mission of tracking a terrorist.

[33] His second screen appearance occurred in Ashutosh Gowarikar's big-budget period drama Panipat alongside Sanjay Dutt and Kriti Sanon.

His third appearance in the horror comedy film Bhoot Police co-starring Saif Ali Khan, Jacqueline Fernandez and Yami Gautam.

[40][41] In 2023, his first appearance in Aasmaan Bharadwaj's directorial debut Kuttey alongside Tabu, Radhika Madan and Naseeruddin Shah was released on 13 January.

[51] Kapoor is an endorser for various brands and products, and was the co-owner of the ISL team FC Pune City before it was dissolved in 2019 due to financial and technical difficulties.