The series was a career highlight for her, launching everything she's been able to accomplish since, but it didn't come without its challenges -- and some of those were challenges her cast-mates weren't having to deal with at all.
One incident in particular, Kaling described as absolutely "devastating" to her young adult insecurities. As a performer and a writer on the venerated NBC sitcom, Kaling played an integral roles in the jokes that made it onto the show, and this was a show that thrived on cringe-y moments and political incorrectness.
And yet, one moment has stayed with her for nearly two decades now. "This is my greatest insecurity and someone just called it out," Kaling told "Good Morning America" on Thursday.
Kaling wasn't the only writer to feature on the show. Several members of the ensemble beyond the few main characters was made up of writers. As she recalled, one of her co-workers -- on a different show's writers' room -- suggested that their character tell Kaling's she could stand to lose 15 pounds.
The actress has been open over the years with her struggle to try and fit the expectations for a young woman in the entertainment industry. At that time in her career, she said she was even up and working out every day before work. And yet, this was still the joke this person came up with.
"I had a reckoning where I'm like, 'People are scrutinizing [me], and not only are they scrutinizing [me], they're verbalizing their displeasure with how I look because I don't look a certain way," she told "GMA." "That kind of dissonance has really affected so much of what I write about [and] the kind of characters I play."
In the years since, Kaling created her own niche, since she didn't really see a place for her in the Hollywood machine. "On TV, if you were really thin, then you could be the lead," she said. "Otherwise, you had to be like 250 pounds, and you had to be the slapstick comic relief. But what was crazy, what was left out, is just like this range of people which is a majority of American women over the age of 24. What if you're like a [size] 12 and you want to just live your life and look cute and date?"
Representation and acceptance of all women's bodies has certainly improved in recent years, but it's impossible to underscore sufficiently the role that Kaling had toward helping Hollywood get there by writing and creating projects for herself and other atypical leads, like her starring role on "The Mindy Project."
Just as she's done for women of all different body shapes and sizes, Kaling has also championed stories by minority leads, including the young Indian-American lead, Maitreyi Ramakrishnan, for "Never Have I Ever."
"It makes me so happy that this show can be on Netflix, 40 million people can watch it, it's number one around the world and it stars a girl who is a young, dark-skinned Indian girl," she said. "She's real, and she dates and boys like her, boys hate her, she goes in and out of drama, fights with her friends, but she's normal and she's the point of view character and so you can look to that and feel seen."
Comedy continues to evolve away from reductive jokes about women's bodies trading on stereotypes and unrealistic beauty standards and Kaling continues to be at the forefront of this new, inclusive, representative and still damned funny revolution.