How Squiffy Became Squiffy

The 5-Year Journey of "Shiver Me Timbers!"

by Steve Stinson



The story first took shape in 2013 when I was planning a book of one-page rhymes and drawings entitled “Ice For Rent.”


The poem was entitled "Up With the Ship." It was about a boy who builds a pirate ship in a tree. But the story didn’t want to be a poem. I couldn’t keep it to one page, mostly because I didn't know where the story was going.


I wanted a story about boys. There would be no adult supervision. There would be no helmets. There would be no batteries. No backlit screens.


 The boys would make their own fun out of whatever materials were available. Perhaps most important, there would be a sense that there was an endless supply of time.


Actually, that was the second most important. The most important: ANY idea that ANY boy came up with would be considered by the others to be the work of genius. In other words, I wanted a story that felt just like the way I grew up.


The story was to be for the 4-8 age group, but experience had taught me that these groupings are meaningless once the book leaves the store. Still, I would stick to the read aloud book basics -- 32 pages, 800 or so words.


At this point all I had was a ship in a tree. I needed a character to make the thing work . . .



Squiffy was born in the first rhyming version of the story, but he wasn’t named Squiffy. He was named Buc (for Buccaneer), then Buck, then Bucko.


If there is a textbook way to develop a character, and I’m sure there is one somewhere, I don’t know it. I just start drawing character studies.


Here is the first character sketch of Bucko:

Cartoonists will tell you a character needs “business.” Business is a package of visual identifiers. It could be a hat or a shirt. It could be a chin. It could be hair. It can be anything. Imagine the character Popeye. He's all business. Pipe, hat, tattoos, swollen arms, bow legs, sailor suit . . .and that face.


But I didn't want a Popeye character. The boys in the stories, although cartoon characters, needed to have one foot in reality, or at least a toe. I wanted the stories to be outlandish, but for the characters to be plausible.


 At this point, Buck looked more or less like me as a boy, so I started to give him some business. I parted his hair in the middle:

I made him thinner. I gave him a t-shirt and jeans. I tried an earring:

I fattened him up and shortened him.  I gave him an eye patch. I gave him a pirate hat. I gave him a  sword. But there was no real magic to Bucko.  Even so, a form began to take shape.

Would the book be black and white, spot color or full color? I wasted a day on this question.

Full color it would be. And now the action could begin:

Bucko would invite boys up to be his pirate crew.     The crew would overload the ship and tip the tree.

Captain Bucko would tell his crew to abandon ship.   When they did the tree would whip back upright.

So far, that was it. Characters in the pirate crew were beginning to emerge. The big kid. The smart kid with a mortarboard. A kid with a chef's hat. A chef's hat?


I anthropomorphised the dog. Gave him a telescope. Seemed clever at first and hackneyed later.


The story got stuck there.  Bucko was thrown through the air. Then what? I decided that Bucko would land in a pig pen. Nice soft place to land. The pig in the foreground of this sketch is based on a character named "Hamlet" from a comic strip I syndicated back in the 1900s. It was nice to see him again.

But landing in a stinkpot, fun as it looks, is not an ending. I was still at "then what?" Nothing in my noggin.' Also, I had met Dawn Wells, the actress who played Mary Ann in the television series “Gilligan’s Island.” The 50th anniversary of the series was approaching and Dawn needed a co-author for a book. I signed on.


I put the whole Bucko file in a drawer.  Maybe lightning would strike later.



By the time I returned to Bucko, I had written two more stories involving a gang of boys.  Like Bucko, they began as rhyme but outgrew it.

The first one, "Brighter Than Air," involved a boy who talks his friends into becoming the crew on his flying ship. They head for the moon.


I got the idea from a painting I did for one of the grandchildren (above). Naturally, the trip to the moon  doesn't go well (right).


The second story was about a boy who sets out to make the world's largest pancake. Soon, he's enlisted all the boys in the neighborhood (below).

The same faces were appearing in the sketches for these stories. An ensemble cast was forming.


The cast needed a leader, an Idea Man in the way the Little Rascals needed Spanky or the way Hannibal, Missouri needed Tom Sawyer.


Bucko couldn't be that man. The character just didn't sing. The name. The look. Bucko, the poor guy, lacked that special something that a ringleader for a gang of boys would need. What was it? The answer was right there in the sketches and painting. He lacked lunacy. plausible lunacy.


That's when I remembered Flamehead, the Unpaid Philosopher:

Flamehead was the Idea Man for the Tri-Area Area in a comic strip I developed in the 1990s.


I did 60 days worth of gags and showed them to some friends. Nobody got it. So Flamehead was also in a drawer.  The comic strip, and by now the comic industry, was going nowhere. But I really liked the guy. Time for a rebirth.


At right is the first sketch of Squiffy, ne Flamehead. I never bothered to do another character study. I'd already done many for the strip, plus sixty days of drawings.


Once the basics of a character are in place it is pointless to continue developing him. Squiffy would emerge on his own after I'd drawn him a few dozen times. Make that hundreds of times.


From where the name? I have no clue. I sketched him. I wrote Squiffy on the sketch. Done. In the UK, to be “squiffy” is to be intoxicated. I didn’t care. I wanted the name and I don’t live in the UK.


A character who is alone in a children’s book is a lonely character. Squiffy would have a gang, but the gang would have to wait.


Another project came up. Before he died in 2010, I promised my father-in-law, NFL Hall of Fame star Bill Dudley, that I would write his life’s story. After the Dawn Wells book, I had access to a publisher. It was time to keep the promise.


Squiffy went back into the same drawer that Bucko came out of.



Time for the gang to assemble. For the pirate story, they would all be secondary players with little dialogue, but I knew they would appear in more than one story. Sooner or later, each character would play a part in moving a story forward. Each would need the kind of personality that could pull his weight.

The first sketches were re-draws of existing characters from other books. Put a pair of glasses on Runnin' Ray (below left) from "Ice for Rent" and he starts to become the math whiz. The two middle guys are from "Grumpypants." The big guy is, well, he's the big guy.  The lower right guy, Teeny, is also a redraw from "Grumpypants."



Three characters emerged quickly. Delbert, Archie and Tank.

Only Tank survived. A few sketches and I had had him. I tried other names, but I liked the period name. Tank was born.


Delbert was modeled on a childhood friend. Anybody who grew up with me would know that no fictional character could ever compete with the real Delbert.


There's no way a Delbert could be a secondary player. Someday, he'll get his own book.  Archie? The name was taken 50 years ago.


But a modified Delbert might work. I also grew up with a guy name Stinky – also a character in real life, but much less attractive than Delbert in every way.


I drew the Delbert character, an attractive character, and put three cartoon stink lines over him, and thought I had him. He was Stinky and attractive at the same time.


I didn't like the name. For that matter, back in real life I didn't like Stinky. But there was another word. A word the grandchildren just love to say . . .

And Stinkbug was born.



With Stinkbug and Tank in the gang, I wanted a boy who was very smart, but always wrong. Maybe he would be a math whiz, but every calculation would be off in a spectacular way. How far is the moon? About a hundred miles. He also had to be agreeable. Every member of the gang would trust his intellect above all others.

In the early stages, I tried the usual stuff that identifies a smart kid. Glasses. Mortarboard . . .

But in the end, I returned to "Flamehead." It was too easy. The character "Garth" in "Flamehead" was fully developed as the resident Know-It-All. I just had to drag him from one world into another:

It didn't take long. Wiry hair. Bow tie and suspenders and he became Katz, which created a problem. In a read aloud book, a child will hear Cats. I could change the name, but that would be too easy. And I liked Katz. Secret: Katz bears an uncanny resemblance to an attorney friend of mine.

If you draw enough over the years, you find yourself turning to the same bits here and there.  For me, one of the bits is the pencil behind the ear, especially for dog characters. Katz got one and he became Katz Who Carries a Pencil. On that same day, Tank became Tank Who Weighs a Ton.


A pattern was forming. You could call it a naming convention.



There would be a cowboy in the gang. There had to be a cowboy, if for nothing else the chance to draw the boots and hat. He would be no-nonsense. He would speak rarely, if at all. He would be the guy who saves the day. In the naming manner of Katz Who Carries a Pencil and Tank Who Weighs a Ton, he became Brero the Vaquero, which created a problem.


A child in the audience who doesn't speak Spanish would not know what a vaquero is. I mulled on this for maybe ten seconds before I decided I didn't care. The translation was visual. He looks like a cowboy.


When I was a boy, there was a television series starring a cowboy named Lash Larue. Lash saved the day using a bullwhip. I didn't want a bullwhip, so Brero got himself a lasso and then I gave him full blown Will Rogers talent.

But Brero didn't have that cowboy way about him, until the day I drew him with his hat covering his eyes – a genuine cowboy look. From there forward, Brero's eyes would never show.



I now had four characters, plus Squiffy. I wanted five. Five makes for better design setups. But I also had a pair of characters I wanted to use. This pair appeared first in the story about the world's largest pancake. They spoke in rhyme and finished each other's sentences.

Here they are describing some of the ingredients for a well made pancake:


“Cookies, cupcakes . . ." said Dan.

"And bubblegum,” said Don.


“Strawberries, cherries, grapes..." said Dan.

"And plums.” said Don.


So, I lifted Dan and Don straight out of the story and made them twins, which makes six characters that seem like five. However, I didn't want to draw identical twins. It would be confusing for the children in the audience and it would have been a burden to draw. Twins are easy. Identical is hard.

But it isn't so bad to draw almost identical twins.



The pirate story needed more players. I couldn't overload the ship with just six gang members, so I brought in the soccer team. Mostly this was a design conceit. The team members would be identifiable by their uniforms. I wouldn't have to come up with eleven more fully developed characters. It also helped with design. As a group they could be a color block on a layout.



The dog and the squirrel are stand-ins on the pages for the children in the audience. They are observing the story as it develops just like the children are observing the story as the pages turn. They are non-character characters. That's why they are nameless.


But they are different non-characters. The dog sees himself as a gang member. The squirrel is an innocent bystander, a witness who gets caught up in the chaos.

I felt that the squirrel, as an unattached witness, should not acknowledge Squiffy or the pirates.


They are creatures from different worlds who are temporarily caught up in the same one.


Here are Squiffy and the the squirrel in sketches for two-page spreads. This is the part of the story where Squiffy and squirrel remain aboard after the crew abandons ship and the tree begins to shiver.



The hardest part of a story is usually the middle. You've got a beginning – boy gets in trouble –  and you've got an end – boy gets out of trouble. How do you get from one to the other and keep readers engaged?


It was now the later days of 2016. Squiffy had been on my mental rotisserie off and on for three years. So far, I had four pieces of middle and an end that wasn't an end to go with a cast of characters ready to perform.


The action in the four pieces of the middle could be dispatched in 6 seconds in a Zig & Sharko animation. This is the difference between plot and story. The four pieces needed to build a story.


It was time to close this thing or drop it. Once again, I returned to my Missouri upbringing.


Tom Sawyer and Huck Finn were a routine presence in my childhood. We lived a few hours drive from Hannibal, Missouri, Twain's home town. I'd seen Aunt Polly's house and the whitewashed fence. I'd been on a tour of "Injun Joe's Cave."


And I read the books. I read Tom Sawyer as a youth. I read Huck Finn too many times to count as an adult. In both books, the boys imagine themselves to be pirates.


In "The Adventures of Tom Sawyer," Huck, Joe Harper and Tom set off on a raft to be pirates on the Mississippi River. Here's an excerpt:


"They shoved off, presently, Tom in command, Huck at the after oar and Joe at the forward. Tom stood amidships, gloomy-browed, and with folded arms, and gave his orders in a low, stern whisper:


"Luff, and bring her to the wind!"


"Aye-aye, sir!"


"Steady, steady-y-y-y!"


"Steady it is, sir!"


"Let her go off a point!"


"Point it is, sir!"


As the boys steadily and monotonously drove the raft toward mid-stream it was no doubt understood that these orders were given only for "style," and were not intended to mean anything in particular."


In an early chapter of  "The Adventures of Huckleberry Finn," the pirate trio has grown into a gang. In both cases, Tom Sawyer is the resident expert due to his extensive reading of pirate literature, even when he admits he doesn't know what he's talking about.


Here's an excerpt:


"Now," says Ben Rogers, "what's the line of business of this Gang?"


"Nothing only robbery and murder," Tom said.


"But who are we going to rob? houses- or cattle- or-"


"Stuff! stealing cattle and such things ain't robbery, it's burglary," says Tom Sawyer. "We ain't burglars. That ain't no sort of style. We are highwaymen. We stop stages and carriages on the road, with masks on, and kill the people and take their watches and money."


"Must we always kill the people?"


"Oh, certainly. It's best. Some authorities think different, but mostly it's considered best to kill them. Except some that you bring to the cave here and keep them till they're ransomed."


"Ransomed? What's that?"


"I don't know. But that's what they do. I've seen it in books; and so of course that's what we've got to do."


I adopted the format with Squiffy in the Tom role. When I started to throw in pirate lingo, the book almost wrote itself. When I got to the phrase "Shiver Me Timbers," I re-drew the middle illustration and the title wrote itself.



If you want to use every available page in a 32-page picture book, the math works out to 14 spreads and one single at the end. I had my spreads designed and most of them were painted.


That single would be the home of the ending I knew I didn't have.


It was driving me nuts. I loved the characters and the action. The thing deserved a great ending, not to mention it wouldn't be much of a book without one. As always, it was back to the beginning.


Question: When we were kids and we got into trouble, made a mess of things, scared ourselves, and then got away with it, what did we do when it was over?


Think, think, think.


Answer: We did it again.


And the final page was done.



A few weeks later I sent four books to Rick Rinehart, the Acquistion Editor at Muddy Boots Books, a new publishing company born of an old one, Globe Pequot. Muddy Boots had a long list of legacy title, but they were looking for their first new fiction.


Two of the books were finished and printed in hardcover. One was paged out in spreads and had three oil on board painted illustrations as samples. I threw in Squiffy as an afterthought. I had paged out the spreads, but the four sample illustrations were three-year old marker sketches that featured the long gone Bucko character.


I was so sure that one of the three submissions, “The First Traffic Jam in Callaway County,” would be the winner that I started painting the rest of the illustrations.


So, it was an odd shock when Muddy Boots let me know I was on board via a short email: "Squiffy Rules!" Details followed.



I knew I wanted the illustrations to be in spreads, meaning they would cross two open pages.


I prefer spreads when I read to children. The kids don't have to search the pages to match up the story and the drawings, and you don't have to point. For me, there is more storytelling opportunity in a spread. I also wanted spreads because I needed the room. There would be eighteen characters in many of these drawings.

In one spread, the boys take an oath to become pirates (Tom Sawyer again). Way too many faces. I gradually narrowed the cast members down to Squiffy and the Vine Street Boys and one soccer team member.

In other spreads, all eighteen characters fit comfortably. I wanted them there. I needed their faces to have readable emotions. Here they abandon ship:

Here they sniff Squiffy fresh from the pig pen:

The big moment in the story is the Shiver Me Timbers! page. Squiffy needed to shiver like no one has ever shivered. I started with sketch of his face and then sketched a spread. The squirrel would be in on the action.

I painted the shiver faces in watercolor. Then I painted a background and photoshopped it in. Then added the text.

The spread needed to be stronger. I painted some flying leaves and photoshopped them in. Still not strong enough. I spread the text across the entire spread. It was getting close. I wanted a child to open this spread and burst out laughing.

I hand lettered the text and placed the letters. It covered too much of Squiffy and the squirrel. I reduced and squeezed the letters and spread them. Done.

The rest of the spreads were finished as watercolors and then cleaned up in photoshop:



From Day One I called the gang "The Ottanots." I loved the name. It was so arch. I loved the idea that there would be a hinge moment in each book when the gang would look at Squiffy and say, "We oughtta not do that."

Muddy Boots balked. Disney has a feature called "The Octonauts." Could a copyright issue arise? The ringside matchup didn't work: Disney big. Muddy Boots not big.


It was almost impossible for me to imagine the boys as anything but the Ottanots. At first I balked, but I had noticed something else. When I pitched the idea to friends and acquaintances, the thing usually required a little nudge, a little explanation. The Ottanots play on words was more clever than effective. It didn't work. It was time to address the problem. Reality tastes better served warm. There would be a new name.

For one long, lame day, it was Squiffy & the Squadfellows. Get it? "Oddfellows" with an "squ" prefix?


Nobody else did either.


And wouldn’t you know that the “Uh Oh Squad” had been used.


So, I tried Squiffy and the . . .


• Should-a-nots

• Shudda-nots

• Scamps

• Shrugokays (Squiffy pitches an idea, they shrug and say “okay”)

• Irregulars

• Oughtnots

• Miscalculators

• O’Missions

• Squires

• Dirt Squirts

• Dirt shirts

• Nod Squad (Squiffy pitches an idea they nod “yes”)

• Egad Lads

• Ynots (Squiffy pitches an idea they say whynot)

• Whynots (Squiffy pitches an idea they say whynot)

• Ricochets

When you aren't sure where to go with an idea, you go back to the beginning. What were these stories supposed to be like? What did I want? I wanted stories that felt like the way I grew up.


I spent my elementary school years at our house near the corner of Fifth Street and Vine Street in my hometown of Fulton, Missouri. That corner opened up to the Missouri School for the Deaf campus, which, as far as we were concerned, was a park.


What if the boys had their headquarters in a similar place? Time to write some backstory . . .

The gang would live in a small town in the Midwest that was surrounded by farms. They would all be in the fourth grade. They would have their HQ in a tree house at the corner of Fifth and Vine.


I couldn't use the tree house in the pirate ship book. Too many trees. But I could use the name, and the Vine Street Boys were born.



I was only sure of one design element I wanted on the cover. I wanted hand lettering. My hand lettering. I mocked up a cover using a crop from one of the spreads.

Muddy Boots wasn't impressed. It didn't pop. It didn't highlight the main characters.


This was actually an opportunity. There was one spread that I was iffy about. It was adequate, but it didn't sing for me. I didn't know why, so it stayed in the lineup. Now, I had a reason to toss it and start over.


I redrew the spread, making sure that it could crop to a single with the main characters grouped within.

Muddy Boots was more impressed, but they didn't like the hand lettered title. Still didn't pop. Plus it would be hard to read on a bookstand. Meanwhile, I decided I didn't like the standard font on Squiffy's name and Vine Street Boys readout.  It all needed to be hand lettered. I started lettering.

I couldn't get the title lettering right. I understood the problem. The lettering was stiff. It didn't dance. I didn't understand how to fix it. This was starting to be like my golf swing. Wrong again, over and over and over. I called a friend and former colleague. What was I doing wrong?


"You're holding your pencil too tight," he said. "Hold it in the middle and don't let your hand rest on the  table."


And Shiver Me Timbers was done.


Muddy Boots had one final edit. Lose the ampersand. Nobody could read it. And so . . .

Done and done.



We had been through most of the normal flow of editing at Muddy Boots when I got a note. What did I think of hand lettering all the pirate lingo? It wasn't a matter of did I like the idea. It was a matter of could I do it and make it fit in the flow of the text.

I drew them large, with a 5 point line.


Then I reduced them and straightened the bobbles and colored them in photoshop.

The mechanical I sent to Muddy Boots was done in Adobe InDesign. The hand lettered words were images placed in gaps in the text. This little design conceit changed the entire flow of the book.

From there Squiffy went to press.


By the way, the frying pan anchor in the first illustration is another nod to Tom Sawyer.


You could look it up...

Copyright ©, 2018, Steve Stinson