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The Optionist · Aug 14, 2026

IP Picks🔎: The Next ‘Road to Perdition’; ‘Secret History’ Meets ‘Yellowjackets’

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Andy Lewis · The Optionist

ROAD TRIP Tom Hanks, left, and Tyler Hoechlin star in Sam Mendes’ 2002 movie Road to Perdition. (Ankler illustration; Everett Collection)

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Welcome to The Optionist. Thanks for reading along with me.

Sixty-six years ago this week, Random House founder Bennett Cerf welched on a $50 bet he lost to Theodor Geisel. It’s a pity he didn’t pay up because it would have been the best $50 he ever spent. You see, the bet led to Green Eggs and Ham, the beloved children’s book, which might also be the best-selling book of all time.

To understand how a bet birthed a kids’ book, we have to backtrack to the mid-1950s when Americans were worried about a crisis of youth literacy, brought on in part because the main book series for beginning readers (Dick and Jane), to put it mildly, sucked. An editor approached Geisel, aka Dr. Seuss, with a challenge: write a fun book using only a list of 348 words important for first-grade readers. It took Geisel a year to figure it out, but he came back in 1957 with The Cat in the Hat — 236 different words, 1,600 total.

Inspired by the success of The Cat in the Hat, Random House put Geisel in charge of a new line of books for beginner readers. He challenged himself to come up with something that used even fewer different words, this time drawing on a list of just 182 for a book aimed at even younger readers. Out of that came 1959’s One Fish, Two Fish.

BET ON IT Theodor Geisel, top right, and Bennett Cerf, bottom right.

Cerf upped the degree of difficulty with the bet: $50 if Geisel could come up with a good book for beginner readers that used just 50 words. Geisel took him up on it — Cerf knew his friend wouldn’t back down from a dare, and indeed Geisel conceded he only did it “to show I could.”

It took a while — rhyming from a list of 50 words, not to mention just coming up with a story, is tough — but Dr. Seuss did it with Green Eggs and Ham. (It should come as no surprise that Brian Jay Jones, author of the definitive Seuss biography, Becoming Dr. Seuss: Theodor Geisel and the Making of an American Imagination, notes it’s probably not a coincidence that the story is about convincing someone to do something they didn’t really want to do.)

The book was an instant hit. Reviewers loved it, and copies flew off the shelf. They still do. No one knows the actual sales numbers, but estimates range from 8 to 15 million to upwards of 200 million copies. It’s probably closer to the higher end than the lower, considering it’s informally known as the bestselling book of all time.

And all that over a $50 dare Cerf never even paid up.

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This oughta be fun in more ways than one. This week, Gallery Books announced that on Sept. 29 it will publish Behind the Castle Walls, former Disney CEO Bob Chapek’s memoir of his three decades at the Mouse House.

The announcement hints that Chapek will spill some tea: “After reflection and distance, Chapek is going behind the scenes” at Disney to reveal “for the first time the high-stakes maneuverings that unraveled behind the scenes from his 2020 appointment to his subsequent dismissal in 2022.” Add in a mention that he took over just weeks before Covid shut down the world and the whole controversy over Florida’s “Don’t Say Gay” law, and you’ve got lots of potentially juicy information.

What’s also going to make this fun — and which surprisingly none of the news stories about the announcement noted — is that Behind the Castle Walls drops just a week after Ari Emanuel’s memoir, Roll the Calls, is published on Sept. 22.

Ari’s already begun upping his image polishing — with a couple of New York Times pieces (here and here) and his WSJ op-ed defending the Paramount Skydance acquisition of Warner Bros. Discovery — ahead of what should be an extensive PR campaign. (You don’t hire Prince Harry ghostwriter J.R. Moehringer unless you’re trying to make a splash.)

But it’s hard to believe that Chapek’s book won’t stunt Ari’s news cycle. First, there’s the inherent curiosity around Chapek’s ouster and his relationship with Bob Iger. Second, Disney is a bigger brand than any of the companies Ari’s been associated with, making Behind the Castle Walls an easier sell to the broader public. Third, traditional corporate CEO memoirs are the bread and butter of business books. It’s an audience not unlike romance readers: You read one, you read them all.

I’ll be watching — popcorn in hand — to see how this all plays out in terms of publicity and sales.

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I know period is a tough sell, but if it wasn't for that, I think the gangster drama with the family twist would be a no-brainer sale. Even with the period hurdle, I still think it’s worth it. There’s also a fantastic true-crime story in the journalism section that could serve as the basis for a prestige limited series. And two new books from fan-favorite YA authors, both working in the New Adult space with their latest.

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💰 A gangster epic in the vein of Road to Perdition and Live by Night that fictionalizes a true story from the Great Depression

🎬 A beloved YA author makes their adult debut with a feel-good romance about two twentysomethings falling in love. (Remaining vague to hide the good spoiler details below.)

🎓A dark academia gem from the author of a popular YA fantasy series headed to the big screen.

🛍️ Hot Tub Time Machine meets Sharp Objects in a potential limited series amateur procedural about an unsolved murder that involves time travel back to the ’90s.

🔪 In journalism, a Euphoria meets Adolescence potential prestige true crime-inspired limited series centered on two teen boys, the murderer and the victim.

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