Funniest Hollywood Roofing Fails

No family Hollywood movie is complete without some sort of home improvement fail. Whether it’s the father trying to set up lights for Christmas or something a bit more classic, like Laurel & Hardy, everyone loves a little rooftop comedy. Check out our compilation of some hilarious roofing fail moments from movies, television, and the internet.

Home Improvement


We all remember this Tim Allen classic! A hilarious show within a show, Tim Allen gave us some great tips on his show Tool Time. Tim “the Toolman” Taylor didn’t know what would happen when he hopped into and through this unstable part of the roof, but we all got a laugh out of this roofing fail — including his rival, Bob Vila.

Four Christmases


While this family movie is fraught with crazy moments and tension, who could forget the moment that Vince Vaughn fell off the roof, along with the satellite dish. He may have been trying to escape spending time with his family during Christmas, but his failure is our laughter.

Dirty Work


Laurel and Hardy have written and performed some of the most classic moments in television history. While completing some cleaning and home improvement tasks, the two find themselves in a series of unfortunate situations that result with both of them dirty, and full of bumps and bruises.

The Money Pit


In an epic spill that ends up taking out the entire the entire project, Tom Hanks brings down the chimney and destroys scaffolding, spills paints, and breaks just about everything. It’s no wonder home renovations are known to be money pits!

The Santa Clause


Tim Allen seems to have a serious penchant for roofing fails, and here is another movie where he’s involved a roof related tumble. While he’s not the one falling off the roof this time, he is the one that surprised an unaware Santa Clause into a fall. Tim Allen will find himself on plenty of roof tops as a result of his bumble.

National Lampoon’s Christmas Vacation

Christmas is a popular time of year to be on the roof, hanging lights and putting up decorations. It’s also great fodder for movie scene tumbles, as we can see from the ultimate roofing fail brought to us by Chevy Chase. The only thing that saved his life from death during this moment was a very sturdy gutter.

Don’t End Up Another Movie Style Roofing Fail

While movies are mostly fantasy and make believe, there is always a grain of truth in them. From this choice selection of classic films, we can see that getting up on the roof any time of year can be very dangerous. Don’t put yourself at risk of a home improvement fail or a roofing fail, reach out to Custom Home Remodeling & Roofing whenever you need to complete roof related repair or cleaning!