How to Fail as a Popstar is a Canadian comedy web series, which premiered on CBC Gem in 2023.^[1] Adapted from Vivek Shraya's stage play and subsequent book of the same name, the series dramatizes Shraya's early attempt at becoming a pop music star in the 2000s before finding greater success as a writer.^[2]

The series stars Chris D'Silva as Shraya in childhood and Adrian Pavone as Shraya in young adulthood, with Shraya personally narrating and appearing to her younger selves in dream sequences.^[2] The supporting cast includes Ayesha Mansur Gonsalves, Nadine Bhabha, Arwen Humphreys, Eric Johnson, Vanessa Matsui and Aayushma Sapkota.^[1] Matsui was also the director of the series.^[3]

According to Shraya, the idea behind the play, book and series adaptation was to normalize talking about failure, an experience that many people share but which is rarely depicted in scripted entertainment.^[4] Concurrently with the series premiere, Shraya also released an album of music from the series, including both older tracks recorded during that era of her life and newer songs.^[5]

The series had a theatrical preview screening at the 2023 Calgary International Film Festival,^[6] in advance of its CBC Gem premiere in October 2023.^[2]