Oberoi made his debut in Ram Gopal Varma's Company. The film was a critically acclaimed hit and his performance was applauded. He received Filmfare Awards in the Best Debut as well as the Best Supporting Actor category. He then starred in the action films, Road and Dum, in which his performance was appreciated. He starred alongside Rani Mukerji in Yash Raj Films Saathiya (2002) directed by Shaad Ali. The film was critically and commercially successful though it was attributed more to Rani Mukerji's appeal. However he received Best Actor nominations at various award functions. He also starred in the comic film Masti (2004) with Aftab Shivdasani and Riteish Desmukh. The film in spite of negative reviews became a surprise box office hit. He also starred in the critically acclaimed film Yuva, in which he was very much appreciated for his performance. His 2005 release Kaal (2005) was also successful.

He was also a part of Mani Ratnam's stage showin Tamil, Netru, Indru, Naalai. In 2006 he appeared in Omkara an adaptation of Shakespeare's play Othello which was critically acclaimed in India as well as overseas playing the character of Kesu based on the character Michael Cassio in the original play. In 2007 he won acclaim for his role as the gangster Maya Dolas in the multi-starred Shootout at Lokhandwala.

His next film will be Mission Istanbul directed by Apoorva Lakia and the film has a huge cast which consists of Abhishek Bachchan, Bobby Deol, Tusshar Kapoor, Shabbir Ahlluwalia and one more actor will also be in the movie.Vivek is thinking about acting in Salaam-e-ishq 2.