Insell has worked predominantly in local theatre, including productions of
James and the Giant Peach The Rocky Horror Show, and
Ride the Cyclone but has also had credits on a number of television films produced by Front Street Pictures for the
Hallmark Channel, He also appeared as the
drag mother to British Columbian rapper
bbno$ for the music video for his song "imma". in 2022He appeared on the
first season of ''
Canada's Drag Race'' in 2020, emerging as a popular fan favourite and winning the key
Snatch Game challenge for his performance as
Joan Rivers, but was eliminated from the competition in fourth place behind finalists
Priyanka,
Scarlett BoBo and
Rita Baga. For
Fierté Montréal's special online edition of its annual Drag Superstars show, which featured all of the ''Canada's Drag Race'' queens in prerecorded video performances, Jimbo performed a drag recreation of
The Buggles' 1979 hit "
Video Killed the Radio Star". Following ''Canada's Drag Race'' he toured the United Kingdom as part of the Klub Kids show with
Rock M Sakura and Erika Klash, 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; however, he did participate alongside Priyanka, Scarlett Bobo and Rita Baga in an online panel discussion as part of the
Just for Laughs festival. 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, Insell has described
House of Jimbo as "the framework of a kids show, but really made for adults", comparable to ''
Pee-wee's Playhouse or The Hilarious House of Frightenstein, and the show reached its Kickstarter goal by the end of October 2020. At the same time the Chemainus-based Riot Brewing Company introduced Jimbo, a boysenberry-flavoured craft beer whose profits will go in part to funding House of Jimbo
. He returned in the third season of Canada's Drag Race'' in 2022, appearing as a guest judge in the episode "Bitch Stole My Look". In January 2022, he was announced as one of the nine contestants on the
first series of ''
RuPaul's Drag Race: UK vs. the World''. After winning the first two episodes of the season, Jimbo's early elimination was dubbed one of the most "controversial" in the history of the franchise. Jimbo returned to the
Drag Race franchise to compete on the
eighth season of ''
RuPaul's Drag Race All Stars'' (2023). After winning a record-tying 4 challenges over the course of the season, Jimbo was crowned the winner of the season and earned a cash prize of $200,000 plus $20,000 for the 4 challenges he won, totalling $220,000. In November 2023, Jimbo signed with talent agencies
WME and
Producer Entertainment Group. In February 2024 Jimbo competed on
Family Feud Canada, with a team consisting of his siblings Jeff and Rebecca, and Jimbo's and Jeff's husbands. At the 2025
Just for Laughs festival, Jimbo and his ''Canada's Drag Race
castmate Lemon taped a roast battle for the fifth season of Roast Battle Canada''. In February 2026, Jimbo was announced as a main judge on ''
Canada's Drag Race All Stars alongside Brooke Lynn Hytes and Priyanka. This makes this panel the first all-drag queen judging panel in Drag Race'' history. ==Filmography==