Naidu's first professional acting job was Touch and Go (1986) which he won from an open call. He starred in the TV movie Lady Blue (1985) as Paquito. This was followed by an ABC Afterschool Specials (1972) episode ABC Afterschool Specials: No Greater Gift (1985), in which he played Nick Santana, a 12-year-old boy with a terminal illness. Naidu then appeared in one of the first-season episodes of the original MacGyver (1985) TV series, MacGyver: To Be a Man (1986), in 1986. Other film credits when younger include Where the River Runs Black (1986) and Vice Versa (1988). Between 1988 and 1995, he worked extensively in classical theater. Naidu returned to film acting in SubUrbia (1996), for which he was praised for his role as the convenience store owner Nazeer Choudhury, and for which he was nominated for an Independent Spirit award for best supporting actor. Onscreen, Naidu starred in the cult film Office Space (1999), as well as appearing in such films as K-PAX (2001), SUBWAYStories: Tales from the Underground (1997), Requiem for a Dream (2000), Bad Santa (2003), The War Within (2005), The Guru (2002), Waterborne (2005), Loins of Punjab Presents (2007), and many others. He co-starred as a series regular in the sitcom LateLine (1998) and had guest-starring roles on the television dramas The Sopranos (1999), The West Wing (1999), and Bored to Death (2009). Naidu has been working extensively with musicians from the Asian underground music movement for many years as a dancer and an emcee. His vocals have appeared on many records, most notably Talvin Singh's Mercury Award winner "OK." In 2006, Naidu directed his first feature film, Ashes (2010), which had its release in 2010 and for which he won Best Actor accolades from the New York Indian Film Festival in New York and the London Asian Film Festival. Naidu's most recent theater credits include 'The Master and Margarita' with the Complicité theater company, a world tour of Shakespeare's 'Measure for Measure' with Complicité, 'The Resistible Rise of Arturo Ui' alongside Al Pacino, directed by Simon McBurney, and 'The Little Flower of East Orange' alongside Ellen Burstyn, at New York's Public Theater directed by Philip Seymour Hoffman. In 2001, Naidu's solo theater piece 'Darwaza' was a sold-out hit at New York's LAByrinth Theater Company.