Insell has worked predominantly in local theatre, including productions of James and the Giant Peach[10] The Rocky Horror Show,[11] and Ride the Cyclone but has also had credits on a number of television films produced by Front Street Pictures for the Hallmark Channel,[7] and on the children's television series Pup Academy.

[13]He appeared on the first season of Canada's Drag Race in 2020, emerging as a popular fan favourite[14] and winning the key Snatch Game challenge for his performance as Joan Rivers,[15] but was eliminated from the competition in fourth place behind finalists Priyanka, Scarlett BoBo and Rita Baga.

[citation needed] Following Canada's Drag Race he toured the United Kingdom as part of the Klub Kids show with Rock M Sakura and Erika Klash,[17] and was the only queen from the season not to appear at any dates on the Canada's Drag Race Live at the Drive-In tour;[18] however, he did participate alongside Priyanka, Scarlett Bobo and Rita Baga in an online panel discussion as part of the Just for Laughs festival.

[19] During the COVID-19 pandemic in Canada, he also created a line of face masks through his design studio, with every purchase matched by a donation of a free mask to a homeless or low-income person,[2] and launched a Kickstarter campaign to fund the production of House of Jimbo, a comedy and variety series he hopes to launch in the future.

[4] After the airing of the season, Jimbo was announced to host her own WOW Presents Plus series, It's my Special Show!, which premiered on August 7, 2023.