World's Largest Jack-in-the-Box, Middletown

March, 2009 by Ray Bendici
giant_jackThe Damned Story: In Middletown sits what is purported to be the world's largest jack-in-the-box: a 50-foot high contraption that has a giant clown head pop out of it once a minute. (I guess one man's "world record" is another's "living nightmare.") In 2008, the owner of Wild Bill's Nostalgia center, Bill Ziegler, already owning a 600-pound clown head that once belonged to Bob Keeshan (aka Captain Kangaroo and Claribel the Clown) and an empty brick silo, was approached by artist Chris Hausback who suggested putting the two together. That they did, and a few months later they had an eye-catching roadside attraction that has been drawing curious visitors ever since. In addition to a huge and eclectic collection of vintage pop culture items, random objects, rare toys and games, magazines, books and all sorts of collectibles, Wild Bill's also is home to the world's "largest bobbing head," a huge reproduction of Bill himself that graces the front of the building. Our Damned Experience: On a clear day in February 2009, we loaded up the "Damned Mobile" and trucked on out to Middletown to see the giant jack-in-the-box -- and the rest of Wild Bill's -- for ourselves. wild_billsWhen we arrived at Wild Bill's the first thing we noticed was the building, which has all sorts of bright and bizarre scenes painted along the outside of the building, a fitting homage to the sideshow midways of yore. The next thing we saw was the jack-in-the-box itself, peeking out from its "box" (uh, isn't a silo a cylinder, not a box?). If you're slightly coulrophobic -- although I would argue "fear of" isn't that same thing as "well-justified and rational intense dislike" -- this could be even more frightening than if it was in motion. Just sayin'. Anyway, we checked it out from a safe distance (if there is such a thing when gigantic clown heads are involved), took a few pictures and then went into Wild Bill's, which is a treat in itself. As mentioned, the building is jammed from wall to wall and floor to ceiling with all sorts of vintage pop culture memorabilia -- and all for sale. As you might expect, Wild Bill himself was behind the counter. Not going too far out on a limb, I'd describe him as an amiable old hippie -- long-hair and beard, tie-dye shirt and friendly. He told us a bit about the jack-in-the-box, but unfortunately the day we were there, they were having problems with the belts that power it -- apparently they were slipping. Bill said that they were getting ready to change it over to a chain drive to fix the problem and that it would be up and running in the spring. wild_bills_bobbleAlthough the jack-in-the-box was out of order, Bill was kind enough to turn on the giant bobbing head for us. It wasn't nearly as creepy as the jack-in-the-box -- what could be? -- but it was still kind of cool. We plan on stopping back in the spring to see the jack-in-the-box in all its glory. If You Go: Wild Bill's Nostalgia is located 1003 Newfield Street (Route 3) in Middletown. It is open to the public during regular business hours (Monday - Saturday 10-6, Sunday 10-4); the jack-in-box and the bobbing head can be seen from the road. Make sure to go inside and explore as there are all sorts of weird and wonderful items to be seen.
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Submitted by Heidi (not verified) on
Pretty cool store. Do not think the "bopping head" was operating, though. The inside of the store is filled with goodies, especially posters, records, movies, and even a porn section for those wandering eyes. Heh. Ended up buying some incense. Blue Nile smells nice.

Submitted by jax (not verified) on
This is a friends father. The shop was also a mafia night club from what i hear and his house is haunted by numerous spirits which the family has learned to live in harmony with. Awesome family! awesome shop!

Submitted by Paul Mac (not verified) on
I just recently went here (July 2014) and the "Jack in the Box" was not working at all. Just sitting eerily silent in an area that looks like it has seen better days. The inside of Wild Bills is absolutely amazing. Crammed wall to wall with so much stuff it makes your head spin. Books, movies, posters, cds, bottles, pins, statues, clowns, and some fun stuff like an ET prop and a life size Arnold Schwarzenegger/ Terminator statue. So much to check out and all of it is for sale! After our visit inside we went and walked as much of the property as we could. On the right hand side of the property sites a few VW cars on top of circus balls so it looks like they are balanced up there. Just past there are some abandoned old boats. A pair of VW buses sit on the property from when they had a paint the buses event, and they are a great site to behold. Wild Bill has started to make what appears to be a haunted house attraction that does look like it will be quite terrifying, and off to the back is a ticket booth and a fun house or something to that effect. Well worth a visit. If you want to know more of my visit or see pictures from our outing message me at or my FB page ... I dont mind at all!!