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Khan began networking and met writer-director Abbas Tyrewala, who gave him the lead role in Jaane Tu... Ya Jaane Na (2008). After producer Jhamu Sugandh suffered with financial difficulties, they gave Aamir Khan, who agreed to finance the film, to finance it. The romantic comedy received raves and was a commercial hit, with total sales of 830 million (US$10 million) around the world. Critics applauded Khan's portrayal of Jai Singh Rathore (Rats), a young boy who does not believe in violence. "The company belongs to debutant Imran Khan, who delivers an effective and restrained performance," Khalid Mohammed said. CNN-IBN's Rajeev Masand called him "the best young actor" of the time, describing his appearance as "unconventional and vulnerable" and revealing that it left "a lasting impression." Khan received the Best Male Debut at the 54th Filmfare Awards, sharing the award with Farhan Akhtar.
Jaane Tu... Ya Jaane Na, Khan appeared in Sanjay Gadhvi's thriller Kidnap, directed by Ashtavinayak head honcho Dhilin Mehta. He was portrayed by Minissha Lamba and Sanjay Dutt respectively as Kabir Devendra Sharma, a kidnapper who kidnasss a girl to settle an old score with her father. The actor was initially reluctant to play the role (calling it "tricky and tough") because he couldn't relate to the character; according to him, he would not have been able to do it without Gadhvi's help and assistance. Khan listened to metal and rock music for a year in preparation for his role. Although the film was a critical failure, critics generally praised him. "Imran Khan is a good abductor who is always two steps ahead of his adversary," Gaurav Malani wrote in a piece for The Economic Times. However, the natural actor could make his lip movements that seem synthetic at times." Kidnap was also a commercial failure.
Khan's latest film in Soham Shah's 2009 action thriller Luck starred Dutt, Shruti Haasan, Mithun Chakraborty, and Danny Denzongpa. Khan appears in a scene with Dutt, Shruti Haasan, a middle-class man in dire need of money and willing to do something about it. In an interview, he said that the stunts (and the "unusual" interpretation of human betting) inspired him to sign the film. When shooting the climax scene, he raked his eyelashes. It was a commercial disappointment and attracted critical attention from critics, as did Khan's performance. Raja Sen of Rediff.com said that the results lacked the spark of his previous ones.
Khan received fewer film opportunities after Kidnap and Chance's demise, until Karan Johar approached him for the lead role in I Hate Luv Storys (2010). The romantic comedy, written and directed by debutante Punit Malhotra, stars Jay "J" Dhingra, a young Casanova who does not believe in the notion of love and romance. Critics generally gave the film favourable feedback; Khan's role was generally well received. "Imran Khan is endearing and does well for a small piece of the film," Komal Nahta wrote. But he does have to improve in emotional situations. In the light scenes, [he] is liberated and lovable. I Hate Luv Storys was a huge success for both domestic and international box-offices, grossing 75.2 million (US$9.1 million). Khan expressed his admiration for Johar's giving him the opportunity. In Danish Aslam's coming-of-age romantic drama Break Ke Baad, he appeared for the first time. The film (and his appearance) received mixed reviews; while Namrata Joshi of Outlook characterized his role as "earnest," Anupama Chopra said.
Khan received raves for his role in Abhinay Deo's English language black comedy Delhi Belly in 2011. Tashi, a journalist caught up in a diamond hunt in Delhi, was mistakenly taken by him and his roommates (Kunaal Roy Kapur and Vir Das). The film opened with critical acclaim and was a commercial success, with domestic sales in excess of 550 million (US$6.9 million). A review in Mid-Day characterized his work as "refreshingly fine," and The Times of India's Nikhat Kazmi said it was his best work to date. "I have always wanted to do this film, and it's very different to what has been seen in Hindi cinema before." Khan appeared in Ali Abbas Zafar's romantic comedy Mere Brother Ki Dulhan later this year. It received mixed feedback, but it was a box-office hit, with domestic sales of over 500,000 dollars (US$7.2 million). Ali Zafar and Katrina Kaif respectively played Kush Agnihotri, a man who falls in love with his brother's bride. Critics lauded his achievements; Sonia Chopra of Sify described him as "instantly likeable" after his appearance;
In Shakun Batra's debut film Ek Main Aur Ekk Tu (2012) with Kareena Kapoor, Khan starred Rahul Kapoor, an uptight architect. The romantic comedy, which is set in Las Vegas, is the story of two strangers who get married one night after getting inebriated. Khan referred to his image as "a man who lives his life according to his parents' wishes." The film's critical reaction and appearance was encouraging, with Rajeev Masand predicting that "Imran Khan slips gracefully into his role." "Imran Khan is a marvelous actor, and he doesn't let down," Mumbai Mirror reporter Karan Anshuman writes. His body language slackens in transition as the script dictates, and he's absolutely on target for his comedic timing." Ek Main Aur Ekk Tu was a modest commercial success, earning a total of 530 million (US$6.6 million) in India and abroad.
Khan appeared in three films in 2013, the first being Vishal Bhardwaj's Matru Ki Bijlee Ka Mandola, a political satire set in Haryana's rustic countryside. Khan co-starred Pankaj Kapur, Anushka Sharma, and Shabana Azmi. Hukum Singh Matru, an educated community activist and Kapur's right-hand man, appeared on Pankaj Kapur. He lived in Delhi for three months and learned to speak Haryanvi from Act One, a theatre company. Critics and observers alike wrote about the film (and his appearance), but it was ultimately poor in terms of potential box-office income. "Imran Khan goes red in the face trying to muster up a Haryanvi accent and act tough," Reuters' Shilpa Jamkhandikar said. You can even see the effort in his performances, which is why it jars all the more." It's best to say that it was a good attempt, at least. In "Chaar Dina Ki," Khan also performed for the film's soundtrack.
In Milan Luthria's period romantic-drama Once Upon A Time, Khan's next film role was alongside Akshay Kumar and Sonakshi Sinha. (A sequel to 2010's Once Upon a Time in Mumbaai). The film and Khan's portrayal of a gangster was mixed. Although Shubhra Gupta of The Indian Express found him unconvincing, NDTV's Saibal Chatterjee said, "He demonstrates that he can perform a wider variety of roles than he is expected to play." He appeared alongside Kareena Kapoor in Punit Malhotra's romantic comedy Gori Tere Pyaar Mein, a social and commercial failure earlier this year.
Khan appeared in Nikhil Advani's romantic comedy Katti Batti in 2015, opposite Kangana Ranaut. The film opened to mixed reviews and was yet another box-office tragedy for him; it was his last release to date.