I am currently in the midst of building the most frustrating and most difficult puzzle I’ve encountered. It is a stylized 1000 piece art puzzle of Pennywise from It Chapter Two. It’s a puzzle released by The OP (Usaopoly), a Southern California-based company that specializes in licensed puzzles and licensed versions of Monopoly. As I struggle with this puzzle I’m not sure if it is difficult by design or difficult by design flaw.

I started this puzzle with one of my sons. We had recently completed a 1000 piece Super Mario puzzle from The OP. That one was challenging because of the subtle color variation and the large sections of the same color and pattern. In looking for our next puzzle, I selected the Pennywise because my son is an It fan (both versions of the movie) and I thought there was enough detail in the art that my son would be able to pattern match and thus stay engaged with the puzzle throughout its build. (He walked away from the Mario one for a period of time, leaving me with the more difficult parts, and then swooping back in near the end to help finish it off.)
When Pennywise was cracked and we got down to the business, I directed my son to start on the little bit of text and then the large spider-web effect while I started the edges. I’ve always been a big fan of building the frame first. I think it helps to see the size of the space in which you are working and the frame often has visual cues that can help you as starting points for your build. This opinion originates with my mom with whom I puzzled as a youngster. I can’t remember for certain but I suspect my mom developed this plan when she puzzled with her mom back in the day. I don’t remember doing puzzles with my grandma, but I do know she and several of my aunts were often doing puzzles. For many years, my sister and I would help my mom pick out a puzzle to send to our grandma for Christmas. My mom would sometimes turn down our selection because it might be too easy for my grandma, who was a seasoned puzzler. I know eventually we stopped sending puzzles as grandma aged. I know my sister and I eventually stopped doing puzzles with mom. My mom and grandma are both gone now but I sometimes think of them both as I work on a new puzzle.
The less hair on my head the more reflective I get.
An hour or so into our first sit down with Pennywise it became apparent to me that building the frame was going to be tricky. There were no discerning characteristics to help determine where the pieces belonged. The pieces were either black, a shade almost black, or a green/black that looked black until you got it alongside one of its fellows. I abandoned the frame and decided to help my son with Pennywise. He had made quick work of the text but had hit a snag with the spider-web. I shifted his focus (and mine) to the blood drip-like effects. I fished out of the pieces and my son put them together. He also had some early success with the mouth of little sharp teeth.
Then the wheels started to come off.
One of the challenges we faced was the cut of the pieces often obliterated any recognizable pattern in the art. Was that dark streak some of Pennywise’s hair, a part of a tentacle, or some of the many areas of brown shadowing on orange? The subtle differences in shades of orange was difficult to discern. Same too for the greens. Same too for the various shades of black.
In an effort to keep my son into the puzzle, I packed up all the black only and green/black only pieces. This left us with a sizable sea of greens and oranges with seemingly nonsensical streaks of browns.

My son wandered off and has not yet fully returned.
I got back into puzzles in 2013. I had brought a number of Schmidt Spiele and Anatolian puzzles into ComicReaders Downtown. The store had always carried licensed puzzles but I had more and more inquiries about more typical puzzles like landscapes. Schmidt Spiele — a board game and puzzle publisher from Germany– and Anatolian– which has its roots in Turkey, I do believe, but has offices in various countries– offered a wide variety of stunning puzzles ranging from 500 pieces to 3000 pieces. My first personal purchase from this line was a Schmidt puzzle of a Napoleonic era British ship. The timing of this find was perfect because I was well along in reading Patrick O’Brian’s Aubrey / Maturin novels. I had done that one on my own and now it was looking like I was going to be flying solo on Pennywise.
Alone, I had several sessions of little or no progress. I even moved the puzzle outside for a day. I thought the natural light would help me better recognize the subtle differences in shades of orange and green. Back inside and under ceiling lights that create glare, I decided the only way I could make progress was to organize the oranges and greens. I did this tedious task, but it really did help. The puzzle mat was now a tableau of different types of oranges and greens grouped together. I tackled each group separately and was soon making excellent progress. I stumbled for a while when I had to build the various tentacles. You’d think by looking at the box art that the tentacles would be easy but the size and design variation is not readily apparent on the individual pieces.
My son checks on me from time to time and gives encouraging remarks and nods of the head to show he’s impressed with my progress. I do feel a sense of triumph for each section I finish. When I placed the last orange and green pieces, thus finishing Pennywise, I called my wife and sons to the basement so I could proudly show off my accomplishment.
Now I am left with a box of black only pieces, almost black pieces, and black/green pieces that look a lot like black pieces until you get them alongside their fellows. I’ve started organizing these various shades. I’ve done much, but the reality is I’ve still got a long way to go. I also know for a fact that this frustrating puzzle is NOT going back in the box when finished. I’m going to glue it, frame it, and hang it on the wall like a trophy. (Chad Boudreau)