Starting off his career by working in music videos and advertisements, Shahid Kapoor made his Bollywood debut as a background dancer in Subhash Ghai's Taal (1999). Four years later, he made his debut as a lead in Ishq Vishk (2003) and won a Filmfare Best Male Debut Award for his performance. Following through with acclaimed performances in films like Fida (2004) and Shikhar (2005), he had his first commercial success with Sooraj R. Barjatya's Vivah (2006), and followed it up with Jab We Met (2007) and Kaminey (2009) which are also his biggest commercial successes so far.
Before starting off his career as an actor, Shahid worked in several music videos and ads, including the Pepsi commercial with Shahrukh Khan, Kajol and Rani Mukerji post Kuch Kuch Hota Hai (1998). While doing so, he decided to join the Shiamak Davar Institute for the Performing Arts (SDIPA), where he was later seen in Subhash Ghai's film Taal (1999) as a background dancer in the song Kahin Aag Lage Lag Jawe along with actress Aishwarya Rai and in Dil To Pagal Hai (1997) of Yash Raj banner with actress Karisma Kapoor.
In 2003, Shahid played his first leading role as Rajiv Mathur, a carefree young man in Ken Ghosh's moderately successful love story Ishq Vishk. Appearing opposite Amrita Rao and Shenaz Treasurywala, the film was well received by audiences and Kapoor's performance earned him a Filmfare Best Male Debut Award. Film critic Taran Adarsh from indiaFM wrote, "Shahid Kapur is an actor to watch. He has all the qualities to hit the top slot. Not only is he good looking, but he is an amazing performer as well. Very original as a perormer [sic], the youngster has handled the dramatic and emotional moments with flourish. He is an exceptional dancer as well. All he needs to do is pick and choose his forthcoming assignments with care, so that the journey to the top slot is minus hiccups."
The following year, Shahid joined once again with director Ken Ghosh in the thriller Fida, where he co-starred alongside Kareena Kapoor and Fardeen Khan. The film failed to do well at the box office, yet Shahid 's performance was praised. The Tribune concluded, "...Shahid Kapoor shines in his role. He looks fresh. As an impulsive emotional and innocent guy, who is sucked into crime because of these very qualities, he manages to evoke your sympathies." He then appeared in the romantic comedy Dil Maange More opposite Soha Ali Khan, Tulip Joshi, and Ayesha Takia. His performance opened to mixed reviews; Rediff.com wrote that "Shahid tends to imitate Shahrukh Khan a lot. He does it well in some scenes, overdoes it in others..."
Featuring in three more films in 2005, success continued to elude Kapoor. However, his performance as Jaidev Vardhan, a man who is sucked into the world of money and greed in John M. Matthan's drama Shikhar was critically acclaimed, earning Shahid his first Star Screen Award for Best Actor nomination. According to IndiaFM, "Shahid Kapoor is only improving with every film. He matches up to Ajay in almost all sequences."
In 2006, Shahid starred in 36 China Town. Revolving around the story of seven individuals and a murder, the film became a moderate success despite receiving mixed reviews from critics. Shortly after the release of the film, Shahid 's second release of the year, Priyadarshan's comedy Chup Chup Ke, followed. The film became a moderate success at the box office.
Shahid 's last release of 2006 was Sooraj R. Barjatya's romantic drama Vivah, a film depicting the journey of two individuals from engagement to marriage. Co-starring alongside Amrita Rao, the film was received favourably by most critics and became one of the highest grossing films of the year as well as Shahid 's second biggest commercial success to date. Shahid 's performance earned his second consecutive nomination for Best Actor at the Star Screen Awards. Taran Adarsh wrote, "Shahid Shahid performs like never before. If he was super-cool in Ishq Vishk and showed flashes of brilliance in Fida, you've to watch him in Vivah to see his growth as a tremendous actor. He is exceptional in emotional sequences."
During the summer of 2006, Shahid embarked on his first world tour, the Rockstars Concert, along with Bollywood stars, Salman Khan, Kareena Kapoor hid , John Abraham, Esha Deol, Mallika Sherawat and Zayed Khan.
In 2007, Shahid appeared in two movies. His first release was Ahmed Khan's Fool and Final. The film received negative reviews and failed to do well at the box office; Shahid 's performance in the film did not receive positive reviews. His next release, Imtiaz Ali's comedy-romance Jab We Met, opposite Kareena Kapoor, became one of the biggest hits of the year. The film tells the story of two people with two very different personalities meeting each other on a train and how they fall in love eventually. Shahid portrayed the character of Aditya Kashyap, a dejected young industrialist full of angst and despair. The film was well-received by critics and Shahid 's performance earned him several nominations for Best Actor at a number of award ceremonies, including Filmfare. Rajeev Masand from CNN-IBN noted, "Despite the risk of being overshadowed by Kareena, his co-star in the film, Shahid Kapur leaves an indelible impression with a performance that is understated and mature, and indeed the perfect foil to Kareena's boisterousness."
Shahid then appeared in the Aziz Mirza-directed film, Kismat Konnection (2008), opposite Vidya Balan. Upon release, the film under-performed at the box office.
In 2009, Shahid portrayed the dual role of twins Charlie and Guddu in the crime film Kaminey. Directed by Vishal Bhardwaj, the film was a critical and commercial success and received mostly positive reviews. Shahid 's performance was also critically acclaimed. Rajeev Masand from CNN-IBN wrote, "Shahid Kapur rises to the challenge of creating two entirely different characters out of Charlie and Guddu, and delivers a credible performance as each. Breaking out of his chocolate-boy image, he gives evidence of his potential when trusted with well-written roles." Later in the year, Shahid appeared in Anurag Singh's romantic comedy Dil Bole Hadippa! alongside Rani Mukerji.
In 2010, Shahid appeared in Ken Ghosh's film Chance Pe Dance opposite Genelia D'Souza, in which he portrayed the role of a struggling Bollywood actor. The movie received poor review from critics, but Shahid 's performance was well received. He then starred in Ahmed Khan's Paathshala alongside Ayesha Takia and Nana Patekar followed by Yash Raj Films' moderately successful Badmaash Company. As of April 2010, Shahid has completed filming for Satish Kaushik's Milenge Milenge, which released on July 9, 2010.