The Gay and Wondrous Life of Caleb Gallo is an American comedy web series created, written, directed by and starring Brian Jordan Alvarez, who plays Caleb Gallo and executive produced by Justin Berns. The series features actors Stephanie Koenig, Jon Ebeling, Antonio Marziale, Ken Kirby, and Jason Greene. The series ran for five episodes on YouTube from January 4 to September 2, 2016. The series explores LGBTQ themes, featuring genderfluid and gay characters.^[1] The show's style has been described as absurdist and surreal.^[2][3] As Jude Dry of IndieWire describes, "Brian Jordan Alvarez uses the traditional sitcom as a foundation to imagine a world a few marbles short of reality."^[4] Steven Horowitz of Paper notes that while the series "may stretch beyond the limits of reality, it's actually deeply rooted in it."^[3]

The Gay and Wondrous Life of Caleb Gallo was funded without a production company, but by an investor. The $10,000 received was split between the first three episodes.^[5] Instead of being produced on a schedule, the webseries was made at its own pace.^[6] Creator Brian Jordan Alvarez served multiple roles while making the show, including actor, director, producer, writer, and editor.^[6] As he explains, "Essentially, I love doing everything myself, so as the production grows, it's a process finding people who I trust to take on parts of the workload that I am no longer capable of doing."^[6]

The Gay and Wondrous Life of Caleb Gallo includes many LGBTQ+ characters and topics, including non-cisgender characters.^[6] According to cast member Antonio Marziale, the show's representation is unique in that "[i]t doesn't have to be this big thing."^[6] As Jude Dry of IndieWire explains, "Dates are walks, siblings are different races, gender is whatever, and sexual preference is something to be tried on like a fabulous hat."