Former First Lady Michelle Obama took the stage with her brother and co-host Craig Robinson for a live-taping of their hit podcast “IMO With Michelle Obama and Craig Robinson” at the 23rd annual Martha’s Vineyard African American Film Festival (MVAAFF). The hosts sat down to chat with Emmy-nominated “The White Lotus” actress Natasha Rothwell in a wide-ranging interview that revolved around her expansive career, why people always confuse her for Michelle Buteau and when we’ll finally see “Who TF Did I Marry?” on the small screen.
“I had no aspirations for Hollywood,” Rothwell told Obama after she was asked about her unique career path. “I thought I was going to be a Broadway theater actor. I thought that Audra McDonald and I would be best friends. I went to college for acting, but I would write my auditions. So writing was a huge part of my process as well. To get spiritual with it, I knew from that moment walking across that stage with my degree in acting, I was walking in my purpose that I knew that I was doing something I had been called to do.”
Natasha Rothwell and Michelle Obama hug alongisde Craig Robinson during Higher Ground’s “IMO with Michelle Obama & Craig Robinson” podcast during 2025 Martha’s Vineyard African American Film Festival.
Courtesy of Arturo Holmes/Getty Images
Rothwell began her career doing everything from improv in New York City to teaching acting in Japan in her early twenties. “I did not know I would be a famous person,” she said. “I had no desire to be. I think I’ve always loved collaborative things. I get joy in that process, and that’s just always been true. That’s why I’ve never attempted standup. People often confuse me for Michelle Buteau, but I prefer improv and sketch.”
The “How to Die Alone” creator went on to get a writing gig on “Saturday Night Live.” Shortly thereafter, Issa Rae plucked her from there to write for the first season of HBO’s hit series “Insecure.”
“At ‘SNL,’ I was the only Black writer,” Rothwell said. “Prentice [Penny] has told this story. On my first day at ‘Insecure,’ I remember raising my hand to talk, and Prentice looked at me and he was like, ‘Why is your hand up?’ It was very hierarchical at ‘SNL.’ If you’re a freshman writer, there were a lot of rules that you had to figure out. And [Prentice] was just like, ‘No, you’re at the table.’ I remember just leaning back, and the openness of the space just blew me away.”
Still, as Rothwell explained to Obama and Robinson, getting offered the on-screen role of Kelli was utterly unexpected. “A month into the writers’ room, Kelli was created on the page,” Rothwell said. “We would do readings in the writer’s room of the character. And I was so focused on writing because it was my first scripted room after ‘SNL,’ I didn’t have any crosshairs on being on the screen. I just knew that when [Issa] would cast the writers to read the scripts aloud, she was always casting me as Kelli. One day, she called me into her office with Prentice, and I was just like, ‘Oh Lord, I’m in trouble.’ They were like, ‘We want you to play Kelli’ I cried, because I went from someplace where I was screaming to be seen to another place that saw all of me.”
Following the success of “Insecure,” Rothwell got a major development deal from HBO, and from there, she began building the character that would be the focus of her Hulu series, “How to Die Alone.” “I was so thrilled because I was able to create a character that was, in no uncertain terms, a love letter to that unhealed version of myself,” she said. “I was able to create the show with the perspective of 20-plus years of therapy, where I can see this character. We called her a Roomba in the writers’ room. Because when you start up a Roomba, it hits every single wall, but it keeps going. Also, you don’t realize that in that effort, they’re cleaning up the space. So I wanted a protagonist that would hit wall after wall after wall, but keep going because that was where my story lived.” Though the series only had one season, Rothwell is thrilled that people got to see and experience Mel.
Up next, the multi-hyphenate talent is working on “Who TF Did I Marry?” based on Tareasa “Reesa Teesa” Johnson’s viral TikTok story. “I was blown away that she fearlessly was telling the story and still believed in love after that,” Rothwell said. “When the rights to the story became available in Hollywood, it was a six-way bidding war. My Big Hattie Productions was kind of a fledgling. I got the opportunity to FaceTime with her, and we just connected. And we beat Shonda [Rhimes], y’all, we got it. I’m thrilled to produce the story and play the role. It’s in line with the mission of centering marginalized voices, lifting them up and hopefully helping people at the end of the day. We’re pitching it next week. The Hollywood process is long and arduous, but hopefully we’ll be on set this time next year.”
Looking ahead, Rothwell told Obama and Robinson that she hopes that young creatives will bet on themselves and look to their contemporaries to anchor them.
“Building that community is so important,” she said. “That’s what got me through my very broke years in New York, was commiserating and working along with other people who were as hungry and ambitious as I am.”
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