25 Expensive Fails That Are Both Hilarious And Heartbreaking

Big bucks go down the drain in spectacular fashion.

We’ve all seen our fair share of epic fails, but when you slap a hefty price tag on them, the cringe factor skyrockets.

As you scroll through these photos, prepare for a rollercoaster of emotions. You’ll find yourself laughing out loud while also feeling a twinge of sympathy. It’s like watching a high-stakes comedy show where the punchline is always, “Oops, that was expensive!”

Each image is a snapshot of a costly misadventure. As you go through these expensive fails, it becomes clear that even the priciest items aren’t immune to a good old-fashioned mishap. There’s something oddly satisfying about seeing these lavish things fail to live up to their price tags.

1. “Yacht Fire In Torquay, UK 28/5/22″

Image source: r/ThatLooksExpensive

2. “Oopsies”

Image source: r/ThatLooksExpensive

3. “In 2003, A Technician Forgot To Log That He Had Removed 24 Bolts During The Maintenance Of The Noaa-19 Satellite, Causing The Satellite To Fall Over And Costing $135,000,000 In Damages”

Image source: r/ThatLooksExpensive

4. “The Museum Ship Uss Sullivans Has Partially Sunk At The Military Park Pier On Buffalo’s (NY, USA) Waterfront”

Image source: r/ThatLooksExpensive

5. “A Mclaren Underwater Due To Hurricane Ian In Miami”

Image source: r/ThatLooksExpensive

6. “I Hope He Has Good And Full Insurance, On Everything”

Image source: r/ThatLooksExpensive

7. “Crashed F-35c Fell Off Uss Carl Vinson Flight Deck Into South China Sea.”

Image source: r/ThatLooksExpensive

8. “Pro-Tip: When Transporting Paint Makes Sure It Is Properly Secured. Especially If You Are Driving In A $90,000 Maserati”

9. “And This Is Why You Call Your Utility Notification Center!”

Image source: r/ThatLooksExpensive

10. “Bus Crashed Through A Glass At The Train Station In Hamburg”

Image source: r/ThatLooksExpensive

11. “When You Live In Svalbard, Norway And Forget To Close The Window In The Office”

Image source: r/ThatLooksExpensive

12. “A 3 Story Mall That Was Still Under Construction Started Making Some Noises From The Metal Structures.. Everyone Was Evacuated And 5 Minutes Later The Collapse Occurred”

Image source: r/ThatLooksExpensive

13. “Giant Beehive Takes Over Roof. That’s A Lot Of Honey”

Image source: r/ThatLooksExpensive

14. “Dump Truck 70 mph+ Hits Interstate Bridge”

Image source: r/ThatLooksExpensive

15. “Discovered That My Porcelain Countertop Was Actually Tempered Glass”

Image source: r/ThatLooksExpensive

16. “I Think We Need Some Aircraft Tape”

Image source: r/ThatLooksExpensive

17. “I Found This Gym Floor In Texas While Scouring Google Earth For A Picture Game Round. Part Of Houston Flooding Maybe?”

Image source: r/ThatLooksExpensive

18. “A BMW Wrecked By A Tree”

Image source: r/ThatLooksExpensive

19. “Ouch!!”

Image source: r/ThatLooksExpensive

20. “Bear Attack In NC State Park”

Image source: r/ThatLooksExpensive

21. “Jetbridge Collides With A Plane”

Image source: r/ThatLooksExpensive

22. “Road In Hatay/Turkey After Earthquake”

Image source: r/ThatLooksExpensive

23. “And I Thought The Car Parking Was Expensive”

Image source: r/ThatLooksExpensive

24. “Over The PA ‘Cleanup On Aisle 4′”

Image source: r/ThatLooksExpensive

25. “Local Dispensary Became A Drive Thru”

Image source: r/ThatLooksExpensive



Chris Wahl

Chris, co-owner of WorldWideInterweb, is a true aficionado of all things internet and meme-y. When he’s not curating the best of the web, you’ll likely find him on the golf courses of Florida.