- Joe's building of a chair with upside-down front legs in Season 3. Adding to the hilarity of the situation, he said that the chair would "be a pain in the ass" to whoever used it, before even realizing what he had done wrong.
- In Season 4, the handymen had to attach wooden boards to the walls of their rooms, and fill in the gaps with cement. Brian M. ended up providing no less than three funny moments while doing so:
- Firstly he installed the boards too far apart, and so instead of using a piping bag he opted to just grab big handfuls of cement and slap them in there, getting the cement all over the wood in the process. When Andrew eventually showed up to check his progress, he ended up standing there totally speechless as Brian continued to get huge lumps of cement everywhere.
- After Brian eventually finished, Andrew pointed to his cement-covered gloves and said that ideally, he should have finished the job without getting his hands dirty. Brian then removed his gloves to reveal that his actual hands were still clean.
- When Brian went back to the job in the final episode, he decided to "fix" things by sanding off the excess cement. All that he succeeded in doing was creating a huge cloud of dust that sent his wife and Andrew into a coughing fit.
- One of the challenges in Season 4 had the handymen destroying their bathroom. Angie in particular winds up opting to smash the toilet ENTIRELY and winds up spending the next several minutes pulling pieces out from the drain. It goes as well as you'd expect.
- "Brian M's problem with this challenge stem from his inadequacies when it comes to screwing. To put it mildly, Brian M's screwing....lacks elegance. And when screwing, elegance should always be the goal."
- Similarly "Angie's screwing could also use a little finesse."
- And Johnnie...well he just likes screwing way too much.
- Brian P is apparently a "virgin screwer who can't get enough" which them culminates with Brian P admitting that "the screws went into his ass."
- Apparently "chemical welding" in Season 5 was the perfect way to bring in a sex joke on the show.
- When Matt built his skateboard chair in Season 5, he specially built it with a reclined back to make receiving lapdances easier. Yes, he did get Simon's wife in to help demonstrate.
- Also Andrew's "Handyman" Cold Open during Season 5, which managed to somehow connect Viagra to handiwork of all things.
- The Casual Danger Dialogue (of sorts) during one of the Season 5 group challenges, where Andrew proceeds to outline the steps that Matt's undertaking with the plumbing (clean, sand, heat, flux etc.) and then without missing a beat adds "and turn off the fire alarm." (Which Matt had forgotten to do).
- Johnnie's "extra" homework involving the steps to soldering copper pipes together, purely because he's asked to sing the steps in his operatic style...particularly the last line.
Funny / Canada's Worst Handyman