He performed in Indian community functions in Boston, Massachusetts, where he was exposed to music, poetry and the plays of Rabindranath Tagore.

[citation needed] Having acted all through school, Chakrabarti's feature film debut came in 2004 in Spike Lee's She Hate Me.

Early in his career, he starred opposite Molly Shannon in The Wedding Weekend and then in Manish Acharya's Loins of Punjab Presents.

Chakrabarti starred opposite Rebecca Hazelwood in Kissing Cousins and made an appearance in the Yash Raj-produced Bollywood film, New York.

[citation needed] Chakrabarti has also composed the theme song "Dhol Beat" for Loins of Punjab, and Sundaram Tagore's Natvar Bhavsar: Poetics of Color.