​Inside Out 2023: Witch Prophet Sets 'Leilani's Fortune' Apart from Other Music Docs Directed by Loveleen Kaur

Starring Witch Prophet, Sun Sun, SATE, Jesse Northey, Brandon Valdivia, The OBGMs
​Inside Out 2023: Witch Prophet Sets 'Leilani's Fortune' Apart from Other Music Docs Directed by Loveleen Kaur
Photo courtesy of Inside Out Festival
Earlier this month, Ayo Leilani released the acclaimed Gateway Experience, her third studio LP as Witch Prophet. Coinciding with this release comes Leilani's Fortune, a film documenting the singer's rise and evolution as an artist, as well as detailing the unique challenges the Toronto-based alt-R&B singer has overcome. An informal and artistic documentary, Leilani's Fortune gets to the heart and soul of who Ayo Leilani is, and what — and who — she stands for. 

Leilani's Fortune is divided into 10 chapters plus a prologue, chronicling Leilani's nomadic upbringing across Toronto, including her bristling as a child at being lumped into African stereotypes, knowing her reality wasn't similar to the starving children shown in commercials. Leilani shares her connection to music and how, in spite of her attempt to live the "straight life" after her son was born, the craft continued to gnaw at her until she could no longer deny its pull.

The film takes us behind Leilani and SUN SUN's love and marriage, as well as their artistic partnership. Similar to her position during performances, SUN SUN remains quietly in the background for most of the film; nevertheless, her pride and joy in Leilani's talent and success radiates through her smiles and laughter throughout. It's inspiring to hear Leilani speak so openly and unabashedly of the first time she saw SUN SUN, and the way their relationship has subsequently inspired her work. In fact, the greatest asset director Loveleen Kaur has at her disposal is Leilani's uncanny ability to be candid and forthright.

The singer candidly recalls the early moments of success she found in Europe, only to come home still struggling to get any local outlets to give her the time of day, and she calls out Toronto media for not supporting Black music and artists.

Documentaries that cover the career (or certain career phases) of an artist generally follow a similar pattern, and Leilani's Fortune dutifully falls in line. However, Leilani's natural charm and willingness to be truly vulnerable while the camera rolls is what separates this film. Just as viewers will be moved by Leilani's struggles, whether it be with her health or her frustrations with the industry, we are thrilled when her career begins to find its groove. 

For Witch Prophet devotees and the uninitiated alike, Leilani's Fortune is a wonderful primer into this fascinating woman's life and artistry. There is a sweetly earnest moment towards the end of the film when she's reliving the release of her debut album, 2018's The Golden Octave, and Leilani expresses surprise that Toronto music publications even know who she was to review her album. "Exclaim!, you know me?" — yes Leilani, we knew you then, and we continue to bow down today.

The 2023 Inside Out festival runs from May 25 to June 4, taking place online and in-person in Toronto. Find details at the event's website.