Friends, I’m traveling to Cape Cod with my family, so we’re on Low Power Mode for a few days. Today’s is another one that I’m very glad to have found. Thanks for reading! Back to live/new tomorrow!
Hamburger Hamlet and …
Today’s newsletter is about the time Oprah Winfrey and film critic Roger Ebert went on a date.
The date of the date—well, our educated guess is that it was August 9, 1985. I’ll explain how we back into that in a minute.
First, this might be a fun piece of forgettable trivia, but the true reason this story survives is what Oprah and Ebert talked about on the date.
In short, they talked about money.
Context: Ebert would have just turned 43 at the time, and Oprah was 31. (43/2 + 7 = 28.5, if you buy into that, just FYI.)
They knew each other because Ebert and his TV co-host, Gene Siskel, had been guests on Oprah’s first TV show a year or two before, in Baltimore. By 1985, she was the new host of a half-hour morning show called AM Chicago for the local ABC affiliate.
The show had skyrocketed in the ratings, and things were moving fast. Oprah had two options on the table, and she was torn:
She could stay with ABC, sign a new contract with a big raise, and turn AM Chicago into a full-hour show that would be syndicated across the country; or
She could take a bigger risk with bigger potential upside by taking ownership of the show and syndicating it back to ABC and anyone else who wanted it—if anyone wanted it.
Oprah revealed the broad details of this story on the 20th-anniversary edition of her show. Then Ebert wrote that he felt like he now had permission to tell the rest of it:
[W]e went to the movies. Afterward, we went to the Hamburger Hamlet for dinner, my treat.
“I don’t know what to do,” she told me. “The ABC stations want to syndicate my show. So does King World. The problem with syndication is that if your show isn’t successful, you’re off the air in three months. The ABC stations own themselves, so they can keep you on. Which way do you think I should go?”
I took a napkin and a ballpoint pen, and made some simple calculations.
Line 1: How much I made in a year for doing a syndicated television show.
Line 2: Times 2, because Siskel made the same.
Line 3: Times 2, because Oprah would be on for an hour, instead of half an hour.
Line 4: Times 5, because she would be on five days a week.
Line 5: Times 2, because her ratings would be at least twice as big as “Siskel & Ebert.”
I pushed the napkin across the table. Oprah studied it for 10 seconds.
“Rog, I’m going with King World,” she said.
They went on two dates, for what it’s worth, and apparently remained friends until Ebert died in 2013—but lots came of the advice Oprah says he gave her!
Now, because Oprah’s date was Roger Ebert … and because he reviewed movies for a living … and because they both said they went to a movie but didn’t say which one, a group of fanatics set out to identify the film based on context clues.
I think they figured it out. Here’s the reasoning:
King World bought the rights to Oprah’s show in September 1985. So, if the deal was on her mind, the date might have taken place around August.
We might assume Ebert chose the movie; this was his forte, after all. If you look at the big movies that were out then, you’ll find Back to the Future as the most obvious one. But if this was the movie Oprah and Ebert saw together, it’s the kind of detail you’d think they would have mentioned.
The other big movie that came out that month was The Return of the Living Dead, but Ebert famously did not like horror movies, so that’s probably out as well.
However, guess what movie premiered on Friday August 9, 1985? Pee-wee’s Big Adventure.
Ebert never reviewed this movie officially, but he did mention it in a newspaper column before it came out, giving it “two thumbs up” in advance, based on TV previews.
And a few years after all this, he said it was his No. 1 “guilty pleasure” movie, based on “how innocent, how playful and how truly eccentric” it was.
How’s that for detective work? It was 41 years ago this week.
O.K., so who gets the quote of the day? I think we’ll give it to Ebert, since he’s no longer with us, and also because I suspect I’ll have more chances to quote Oprah in the future.
How about this one, which feels like it has more to do thematically with liking Pee-wee Herman than with giving Oprah good advice:
“To make others less happy is a crime. To make ourselves unhappy is where all crime starts.”
Make people happy and bet on yourself. Pretty good advice.
See you tomorrow with our back-to-live newsletters!
Other things worth knowing …
NBC News | WaPo: Tuesday's primaries gave something to both wings of the Democratic Party. In Minnesota, progressive Lt. Gov. Peggy Flanagan defeated centrist Rep. Angie Craig 58-40 for the Senate nomination; she would be the first Native American woman in the Senate if elected in November. In Wisconsin, the establishment pulled off a stunning late-night upset: Milwaukee County Executive David Crowley defeated democratic socialist Francesca Hong — the result wasn't called until 2:30 a.m. after 28,000 delayed Milwaukee absentee ballots came in, despite Hong leading in polls by 22 points.
The Telegraph via Yahoo: U.S. intelligence believes Russia could attack a NATO country as early as this fall — ranging from a cyberattack or false-flag drone operation to a small-scale land incursion — with the Baltics and Poland considered the most likely targets. The assessment marks a significant shift: officials previously believed Putin would not attack NATO while still fighting in Ukraine.
The Guardian: American intelligence experts believe Russia was behind last week's explosive-laden drone attack on Leipzig/Halle Airport, U.S. media have reported, as Berlin remained silent on the likely culprit. The security emergency prompted Interior Minister Alexander Dobrindt to break off his summer holiday in Italy and rush to the scene, where he spoke of a "new level of danger" for Germany.
WaPo: New reporting reveals that when Trump slipped out of Turkey last month in a catering truck to avoid an Iranian assassination threat, he brought his most loyal personal aides — but left behind not only the press corps but every cabinet secretary except Pete Hegseth. At least two cabinet secretaries were unknowingly aboard the decoy plane, believing the president was with them. The C-32A carrying Trump flew to Britain under the call sign "Reach 18" rather than the recognizable Air Force One designation.
ABC News: The water level at Lake Mead, the nation’s largest reservoir, hit a record low on Thursday: 1,040.50 feet, breaking the previous low of 1,040.58 feet set in July 2022. The reservoir, formed by the Hoover Dam on the Colorado River, supplies water to millions of U.S. residents in Nevada and Arizona.
AP: A small organ in eastern Germany is the headliner of the world’s slowest concert, playing the same piece of music by composer John Cage at a glacial pace for nearly 25 years. A rare chord change last week — from seven notes to eight — represented the completion of about 4% of the 639-year endeavor. The composition is scheduled to finish on September 4, 2640.
ABC News: Andy Green — the first and only person to break the sound barrier in a car — hits the track in Utah this week trying to reach 350.092 mph or more in a hydrogen-powered car. In 1997, Green set the outright land speed record of 763.035 mph in a car powered by twin jet engines.
Thanks for reading. See you in the comments!

