Her first book, On the Outside Looking Indian is a humorous memoir about her childhood as the child of Indian immigrants in a small Canadian town. The book was shortlisted for the 2012 Stephen Leacock Memorial Medal for Humour.
Her book garnered attention before its release because the popular website Reddit featured the book's spoof back cover recommendation from Oprah Winfrey. Gill has written for Canadian comedy shows This Hour Has 22 Minutes and Schitt's Creek, the National Post and websites such as McSweeney's.
- "Indo-Canadian memoir too funny to read all at once". Winnipeg Free Press, March 26, 2011.
- "Rupinder Gill grew up ‘on the outside looking Indian’". The Globe and Mail, March 24, 2011.
- "4 women on short list for Stephen Leacock Medal". CBC News, April 2, 2012.