Open Mike, the production company behind Channel 4's Comedy Gala, which stars a host of major comedians including Lee Evans, Michael McIntyre and Alan Carr, suggested Channel 4 continue the humour into the ad break.
Channel 4's strategic sales team then found five "up for it" advertisers who agreed to let Jimmy poke some fun at their brands by appearing in, interacting with or commenting on their ads.
During the Gocompare.com ad, Carr will appear during opera singer Gio Compario's trademark high note and attempt to silence the tenor.
Daren Benton, deputy head of strategic sales at Channel 4, said: "This was too good an opportunity to miss. Open Mike and the advertisers have been fantastic to work with.
"Hopefully this will be seen as yet another example of just how creative you can be with the commercial break."
The Comedy Gala took place on Tuesday (30 March) in aid of the children's charity Great Ormond Street Hospital and will be televised at 9pm on Easter Monday.
Channel 4's Strategic Sales team aim to help advertisers think more creatively about how they use the advertising break and were behind the live Honda Skydive ad.