From Tumblr to Book: Droll Pranks for Rich Boys

Last year’s winner of The Great Tumblr Book Search was the delightful Droll Pranks for Rich Boys, an old-timey comedy of manners expertly adapted to the Tumblr format. As the last days of this year’s Great Tumblr Book Search approach, we interviewed editor Wynn Rankin about making a book from a blog, and bringing author Dan Bulla’s puckish young dandies to life. 

How was the experience of creating a book from a Tumblr different than your usual process?

Tumblr is such an amazing vehicle for humor because it allows authors to play with how broad (or narrow) their topics are, how long (or short) their entries are, the pace between posts, visuals, etc. When I look at a Tumblr site as a potential book, I’m thinking the same things—how can we play with the form to make it feel “just right” as a book? That means asking a lot of fun questions: How many entries make for a good collection? What should be “best of” from the Tumblr versus exclusive or expanded for a book? What extras, if anything, do we need to introduce an entire new book-buying audience that isn’t already following it Tumblr? The goal is to make the flipping of pages as much fun as it is to scroll through the posts online.

Droll Pranks for Rich Boys is an all-text Tumblr. How did you figure out the visual style of the book?

From the moment we started talking with the (awesome) author, Dan Bulla, we were both excited about how visuals would really round out the world where these Droll Pranks take place. Dan’s pranks are pitch perfect and immediately evoke mental images, so we wanted to build on that as a way to add something special to the book. The “a-ha!” moment happened as we were talking about small illustrations that were to be sprinkled throughout. We realized that some of the entries just begged to be full scenes, so we added full-page illustrations, as well.

As for the style, we wanted there to be a timeless quality to the lofty world of rich boys and those who prank them. We also wanted there to be a clear sense of the characters, which is how we came to using the same “Droll Prankster” and “’Rich Boy” throughout. With the world and characters in place, we were able to thread together the pranks in such a way that a fun story emerged.

Tell us about the illustrator whom you recruited for this book.

Dan had a very clear vision of the world where these pranks take place in his head, so he, our designer, and I had a series of great conversations where we shared images and photos as inspiration, as well as illustrators we thought would be a natural fit. Ethan Rilly was there from almost the very beginning, as his illustrations have such character and energy to them. The combination of Dan’s droll, efficient style with words paired perfectly with Ethan’s visuals.

What was the most challenging prank to give visual form?

I know this might sound like I’m cheating, but every image we had in mind came together just how we imagined them! Again, it helped that Dan had great notes about what the visuals should be and Ethan’s sketches came in really strong. The conversations we had at the sketches phase were about finding the best way to sell the joke—should the scenes be close in on the Rich Boy or show the crowd responding to the prank? One of my favorite pranks from the Tumblr site was about christening a ship shows of the perfect balance. You can see the Rich Boy getting pranked, the Droll Prankster admiring his own handiwork, and the audience taking it all in.

Which prank would you be most likely to pull on a fellow chap, given the opportunity?

This one makes me crack up every time I see it:

Droll Pranks for Rich Boys will be available wherever books are sold this fall. Do you have a book idea, humorous or otherwise? Apply to The Great Tumblr Book Search by 3/2/15!

We’re looking for the next big book idea, and we’re partnering with Tumblr to find it. Could it be yours?

Use Tumblr to submit a book proposal in one of the following categories:

  • Art: Calling all photographers, illustrators, and anyone else making visually interesting things that would translate well to print.
  • Food + Drink: Are you an epicure? We want to see cookbooks, food memoirs, and whatever else you’re cooking up!
  • Humor: Our past winners were in this category, so keep the LOLs coming.

You could be published like previous winners Sh*t Rough Drafts and Droll Pranks for Rich Boys, or win a Chronicle Books shopping spree. Here’s how to enter, contest ends 3/2/15!

At the Window. Martin Drolling (aka the Elder, French 1752-1817). Oil on canvas. National Pushkin Museum, Moscow.

The girl tracing a picture on the window is the artist’s daughter, Louise Adéone Drolling, a skilled painter in her own right. She was born in Paris in 1797 (and died young in 1831). Her father encouraged her talent for drawing and painting.