Born in the Deol family, he made his on-screen debut in 2005 with Imtiaz Ali's romantic comedy Socha Na Tha.

Deol had his biggest commercial success in Zoya Akhtar's ensemble film Zindagi Na Milegi Dobara (2011).

"[5] Deol made his film debut in the 2005 Imtiaz Ali's Socha Na Tha, a romantic comedy where he starred opposite Ayesha Takia.

[10] Deol had two more releases in the year, the crime film Ek Chalis Ki Last Local and the thriller Manorama Six Feet Under.

was met with critical acclaim, but suffered heavily because of the timing of its release, a day after the 2008 Mumbai attacks, leading to widespread fear of crowded places.

[13] Deol's breakthrough role came in 2009 when he portrayed the titular character in Anurag Kashyap's 2009 neo-noir film Dev.D, a modern-day adaptation of Sarat Chandra Chattopadhyay's classic Bengali romance novel Devdas.

The idea behind the film was conceived by Kashyap during a conversation with Deol where the latter spoke about a man frequenting a Los Angeles strip club like a "modern day Devdas".

received widespread attention for its distinct visual style, experimental soundtrack, and innovative narrative structure which was unprecedented for any Bollywood film.

[15] In a 4 out of 5 star review for The Times of India, Nikhat Kazmi deemed Deol's performance in the film as a "class act".

[16] Deol made a cameo appearance for an Item number in the movie Tera Kya Hoga Johnny in 2010.

[18] In 2010, he portrayed Arjun Burman, an investment banker opposite Sonam Kapoor's eponymous lead in the ensemble romantic comedy Aisha, which also starred Ira Dubey, Cyrus Sahukar, Amrita Puri, Anand Tiwari, Arunoday Singh and Lisa Haydon.

[2][33] He appeared on several magazine covers including the Man's World and the Time Out Mumbai, with titles such as "The New Face of Indian Cinema".