Abhay Deol

Deol made his film debut in the 2005 Imtiaz Ali's Socha Na Tha, a romantic comedy where he starred opposite Ayesha Takia.[6][7] The film garnered mostly positive reviews from critics and was an average grosser at the box-office.[8] Deol's performance in the film was well received. His second film role was 2006's romantic drama Ahista Ahista opposite Soha Ali Khan. Deol's first 2007 release was the ensemble comedy drama Honeymoon Travels Pvt. Ltd. which emerged as a box-office success.[9] Deol had two more releases in the year, the crime film Ek Chalis Ki Last Local and the thriller Manorama Six Feet Under. The latter won the Best Film at the Mahindra Indo-American Arts Council Film Festival in New York City, and Deol won the Best Actor Award.

Deol's sole release of 2008 was black comedy film Oye Lucky! Lucky Oye!. Directed by Dibakar Banerjee, the film had Deol portray a compulsive thief, Lovinder Singh a.k.a. Lucky, and the film's plot follows his exploits.[10] Oye Lucky! Lucky Oye! 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.[11]

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".[12] Dev.D. received widespread attention for its distinct visual style, experimental soundtrack, and innovative narrative structure which was unprecedented for any Bollywood film.[13] 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".[13] Deol appeared alongside Tannishtha Chatterjee in Road, Movie.[14] Deol made a cameo appearance for an Item number in the movie Tera Kya Hoga Johnny in 2010.[15] In 2009, Deol launched a production company Forbidden Films, with Junction being the film to be picked up by the banner.[16]

Deol promoting Zindagi Na Milegi Dobara at a UTV event

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. In 2011, Deol starred in Zoya Akhtar's ensemble comedy-drama road film Zindagi Na Milegi Dobara alongside Hrithik Roshan, Farhan Akhtar, Katrina Kaif and Kalki Koechlin. The story follows 3 friends, who have been inseparable since childhood, had him play the role of Kabir, an architect. They set off to Spain on a bachelor trip for Kabir who is set to be married to Natasha, an interior designer played by Koechlin.[17] He trained to be a deep-sea diver for the film which was filmed in Spain.[18] The film opened to high critical acclaim and grossed ₹1.53 billion (US$21 million) worldwide, surpassing Dhoom 2 in the worldwide gross, becoming the ninth-highest worldwide-grosser of all time for a Bollywood film, at the time of its release. Zindagi Na Milegi Dobara won Best Film among other awards, and Deol received a nomination for Best Supporting Actor for his performance in the film.[19][20]

Deol had two releases in 2012, both of which were political thrillers– Dibakar Banerjee's Shanghai and Prakash Jha's Chakravyuh. In the latter, Deol starred alongside Arjun Rampal as a police informer, but later gets involved in a Naxalite movement.[21] The film received mixed reviews from film critics.[21] Shanghai co-starring Emraan Hashmi and Kalki Koechlin was based on the French novel Z by Vassilis Vassilikos.[22] The film opened to positive reviews and Deol's performance as a bureaucrat/IAS officer garnered much acclaim.[23] Raja Sen of Rediff.com applauded Deol writing, "he wears his inscrutability thickly and delivers a strong performance".[22] The film was a surprise hit and went on to gross over ₹200 million (US$2.8 million) in India.[24][25]