This isn't the weirdest wing, but I saw someone's photos from the New England Air Museum the other day and was surprised to see a large flying boat I was unaware of. Turns out it's the the "last remaining American-built commercial trans-ocean four-engine flying boat."

The VS-44 was originally developed as the XPBS-1 patrol bomber (see last image), for a requirement to create a larger alternative to the Catalina; however, consolidated won the contract with the Coronado. Two prototypes were built, and both were put into service in WWII, but both were eventually lost. 

Then Sikorsky saw the opportunity to rework the design as a luxury passenger flying boat, hoping to sell it to Pan Am. Three were built, but a Pan Am order never happened. 

The three were originally used in WWII as well, and then entered civilian service. Two were eventually lost, and the third, the Excambian, wound up stranded in Peru. It was then brought to Long Beach, fixed up, and used on a route to Catalina Island. 

Later, it was sold and used to hop around the Virgin Islands. It was finally damaged in the late 60s and converted to a hot dog stand for a spell. 

Excambian began a two decade donation and restoration journey in the 70s, and finally reached the New England Air Museum in 1997 where it's still displayed. 

Source: wikipedia and various websites for the photos