He made his debut as a feature film Director with ...Jayate, a part of the Indian Panorama 1999-2000 at the International Film Festival of India (IFFI), Hyderabad. This was later followed by Dil Pe Mat Le Yaar!! (2000) a bittersweet migrant tale set in Mumbai. This film, though not a huge box-office success continues to enjoy a following for its dark humour and its exploration of life on the fringes of Mumbai. Later that year he came up with Chhal (2002) a stylised gangster film that met with more praise than his previous films. By his own admission the films post-Chhal were disappointing and his career entered a phase where he flirted with formulaic mainstream themes. He made his presence felt with a short film in Dus Kahaniyaan, (2007) titled High on the Highway, which was basically a retelling of a short (Highway) that he directed for television in 1995, based on a script by Vishal Bhardwaj . In 2008 after the release of Woodstock Villa he went on an extended sabbatical to explore life as a foodie, Entrepreneur and to explore themes that mattered to him.