Shahid started his career by working in music videos and commercials. He made his Bollywood debut as a background dancer in Subhash Ghai’s Taal. Four years later, he worked as a lead in Ishq Vishk which won a Filmfare Award for Best Male Debut. He then acted in movies like Fida, Shikhar (2005) and later Vivah, his first commercial success. He then acted in Jab we met and Kaminey, both of which gave him the Filmfare Best Actor nominations.

His parents (actor Pankaj Kapoor and classical dancer Neelima Azeem) divorced when he was three. After the divorce, he lived with his mother and maternal grandparents in Junaghad.

In 2009, He Kapoor portrayed the dual role of twins Charlie and Guddu in the Kaminey which was a commercial success. His performance in Kaminey was also critically acclaimed. Later in the year, he acted in Dil Bole Hadippa!, which bombed at the box office. In 2010, He acted in Chance Pe Dance opposite Genelia D’Souza, in which he portrayed the role of a struggling Bollywood actor. He then starred in Paathshala, Badmaash Company and Milenge Milenge. In 2011, He appeared in Mausam, a movie directed and written by his father Pankaj Kapoor. His performance in the film was well received.