In 2019, Feldstein had a recurring role as Jenna in the first season of the television horror comedy series What We Do in the Shadows, an adaptation of the film of the same name. Her performance earned positive reviews from critics. She was not able to return for the second season, as was originally planned, due to other filming commitments.
Also in 2019, she starred in Olivia Wilde's directorial debut, the high school comedy Booksmart. Her performance garnered widespread critical acclaim and a nomination for the Golden Globe Award for Best Actress – Motion Picture Comedy or Musical. She later portrayed the British lead character Johanna Morrigan in the coming-of-age comedy film How to Build a Girl, which was an adaptation of Caitlin Moran's 2014 novel of the same name. The film and her performance garnered positive reviews from critics.
On August 6, 2019, it was announced that she will star as Monica Lewinsky in the third season of American Crime Story, subtitled Impeachment. On August 29, 2019, it was announced that Feldstein would be starring in Richard Linklater's film adaptation of Merrily We Roll Along, which would be shot over the course of twenty years. Principal photography of the first section of the film has already been completed. Feldstein is set to star alongside Ben Platt and Blake Jenner.