[11] He studied at Wesleyan University during his third year, focusing on identity and race, globalization, and "the impact of popular culture on society.

[27] He has also appeared a number of times on British television, including on Russell Howard's Good News in 2011 and 8 out of 10 Cats in 2012.

[28] He has also performed at the Edinburgh Fringe Festival[29] and was a featured comedian for the US State Department-sponsored "Make Chai Not War" comedy showcase in India in 2012.

[37] In 2018, he spoke about his experience of teaching a workshop at the Columbia River Correctional Institute Comedy School in North Portland as a guest on Live Wire!

[38] Kondabolu's humor often centers on social issues such as poverty, racism, and a rejection of Indian stereotypes seen in media.

Past guests have included Ajay Naidu, Aasif Mandvi, Bell, Leo Allen, Victor Vazquez (Kool AD of Das Racist), Charles Mudede and Blue Scholars.

[43] He also debuted as a rotating host on The Bugle alongside Andy Zaltzman in the fall of 2016 after the departure of John Oliver.

[44][45] Kondabolu wrote and starred in Zia Mohajerjasbi's 2007 short film Manoj,[46] which has played in comedy and film festivals around the world, including the Just for Laughs Festivals in Montreal and Chicago, and which mocks comedians who broadly exploit their ethnic backgrounds for their material.

Kondabolu portrayed "Crossword Businessman" in the 2009 film All About Steve,[48] a movie he mocks in Mainstream American Comic.

[54][55] The film contextualizes Apu within minstrelsy and other tropes in American pop culture history that have historically stereotyped minorities.