The film stars Rachel Sennott as Sam, a stand-up comedian living in Toronto who is struggling with depression that has impacted her career after Brooke (Olga Petsa), a young girl for whom she previously served as a nanny, goes missing.

Sabrina Jalees, Caleb Hearon, Ennis Esmer, Dani Kind, and Jason Jones also star.

Brooke's father is oblivious to the appeal of Sam's comedy initially, but later appears to warm to it more, showing his friends clips of her performances online, which include content around her dating and sex life.

I Used to Be Funny premiered at the South by Southwest festival on March 13, 2023,[4] with Levelfilm acquiring distribution rights in Canada.

The website's consensus reads: "Bringing a droll edge to deeply serious subject matter, Ally Pankiw's feature length debut provides Rachel Sennott a welcome opportunity to display her dramatic range.

"[12] Metacritic, which uses a weighted average, assigned the film a score of 74 out of 100, based on 13 critics, indicating "generally favorable" reviews.

[13] Jason Bailey of The Playlist wrote that "the flashbacks are reasonably well-integrated, though it takes a few scenes to hook into what they're doing and where we are, and some of the stylistic devices to signal them are a little shopworn (there are copious echoing voices haunting the soundtrack).

The worry in these kinds of movies is that the effort to obfuscate and hint at the heart of the problem doesn't pay off.

But the reveal here is thoughtfully constructed (a courtroom scene shows the humiliating way jokes can be taken out of context to serve a prosecutor's favor) and further clarifies Brooke's decision to abandon her family.

It's a humorous touch to this contemporary story about reconciling the past by taking control of the present, and using your gifts to get you out of the dark.

"[14] Peter Sobczynski of The Spool was more negative, writing that "Ultimately, I Used to Be Funny proves to be as aimless as its heroine, though nowhere near as interesting.