9. Popeye the Sailor’s Water-Filled Hat Splashes Onlookers, 1957

Popeye suffered a Macy's Thanksgiving Day Parade balloon mishaps when water pooled in his hat.
The Popeye balloon in 1957. Image via Macy’s Thanksgiving Day Parade

The indented hat of a Popeye the Sailor balloon filled with water when it started raining at the 1957 Thanksgiving Day parade. The weight of the water caused Popeye to tip forward a bit and stray from his intended course. This deviation in the route took him closer to the crowd, which got a chilling surprise. Eventually, the water started to pour out of Popeye’s hat, directly onto an unlucky group of nearby spectators.

Olive Oyl Thanksgiving Day Parade balloon mishap
Photo by Richard Roth Jr.

Popeye’s love interest Olive Oyl also suffered a parade day mishap in the 1980s. Untapped New York reader Robyn sent in the above photo of the incident taken by her father, Richard Roth Jr.

You can see that Olive Oyl’s left hand is severed from the rest of her deflated arm. Her wrist caught on a lamp post or a tree at 72nd Street and Central Park West. According to Robyn, someone had to climb the lamp post to cut the balloon down!