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Later that same year, Kapoor collaborated with Priyanka Chopra on Anand's Anjaana Anjaani, a comedy-drama involving two strangers who vow to commit suicide on New Year's Eve.
The film was a moderate financial success, but garnered little praise from the critics.
His most widely seen film in this period came with the political drama Raajneeti (2010).
The romantic drama Rockstar (2011), in which he played a troubled musician, and the comedy-drama Barfi!
Ronnie Scheib of Variety praised Kapoor for successfully channeling Chaplin in "tone and affect", and Raja Sen of wrote that "he does very strongly indeed with this Chaplin-tribute role, bestowing his character with heart every step of the way".
Kapoor achieved further success in 2013 when he reunited with director Ayan Mukerji for the romantic comedy Yeh Jawaani Hai Deewani co-starring Deepika Padukone, Kalki Koechlin, and Aditya Roy Kapoor.
The film was his first commercial success, in which his role was that of a womaniser who is romantically involved with three women, played by Bipasha Basu, Minissha Lamba, and Deepika Padukone, at different stages of his life. In Dharma Productions's Wake Up Sid, a coming of age film from director Ayan Mukerji, Kapoor portrayed Siddharth "Sid" Mehra, a rich, lazy teenager whose life undergoes a series of changes after interacting with an ambitious journalist (played by Konkana Sen Sharma).
When Mukerji narrated the then-untitled script of the film to him, Kapoor came up with the title himself.
In an interview with the news and entertainment portal Rediff.com, Kapoor stated that his character was written as a tribute to his grandfather's iconic roles as a tramp.
Directed by Anurag Basu, the film (set in the 1970s) tells the story of its titular protagonist (a deaf and mute man, played by Kapoor) who falls in love with a woman who is already engaged (played by Ileana D'Cruz) and later, an autistic girl (played by Priyanka Chopra).
In preparation, Kapoor observed the work of actors Roberto Benigni, Charlie Chaplin, and his grandfather.
Rajeev Masand noted that Kapoor "struggles with a badly-defined role" and NDTV's Anupama Chopra concluded: "Ranbir tries hard to salvage the film, dropping his shirt several times but even his lovingly shot chest can’t save the film." Following an item number in the children's film Chillar Party (2011), Kapoor took on the role of Janardhan "Jordan" Jakhar in Imtiaz Ali's Rockstar, a drama that follows the journey of an aspiring musician from a humble background to international stardom.
In preparation for the role, Kapoor lived with a Jat family in Pitam Pura and studied their mannerisms. Kapoor is the recipient of several awards, including six Filmfare Awards.