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Unlucky in love, lucky in... absolutely nothing else
Charlie Brown left the world as he entered it: confused
Charles Schulz's retirement took the world a little by surprise. Following a period of failing health, Schulz announced on Dec. 14, 1999 that he would end Peanuts. He could no longer see clearly, he'd been diagnosed with colon cancer, and he needed to focus on his health. As a result, Peanuts came to a relatively sudden stop nine weeks later, after newspapers had worked through Schulz's existing backlog.
Schulz passed away in his sleep on Feb. 12, 2000, the day before the last Peanuts strip ran in newspapers. At its end, Peanuts had run for 49 years and 4 months, give or take, for a total of 17,897 strips. He had never taken a sabbatical in that time or had any assistants.
As a result of Schulz's abrupt medical retirement, the last few weeks of Peanuts' run can best be described as "business as usual." Fans had speculated for years about what might happen in the final days of Peanuts, as much of the strip was built around failure-themed running gags. Would the Great Pumpkin finally show up? Would Charlie Brown finally kick the football? Maybe the often-mentioned/never-shown red-headed girl would show up, or Charlie Brown would finally manage his team to a winning baseball game.
None of that happened. Schulz had to retire faster than he ever thought he would, so Peanuts never came to any sort of organized conclusion. It just stopped. There are a couple of strips in the final run that can be read as having some subtext on the subject, most prominently Peppermint Patty's last appearance, but Schulz didn't get the time to set anything up. All we received was the goodbye, because it was all he could give.
In his last televised interview, Schulz recounted the story of drawing the last Peanuts strip to Al Roker and mentioned he'd had an uncharacteristic fit of regret. "All of a sudden, I thought, 'You know, that poor, poor kid, he never even got to kick the football!'" Maybe Schulz might've done something with that if he'd had more time. Sadly, we'll never know.
Charlie Brown and Snoopy's last appearances in Peanuts are technically in the first two panels of the Feb. 13 strip, but that's little more than an optional introduction to Schulz's farewell message. (The first two panels in American newspapers' Sunday comics are often written/drawn as a disposable throwaway gag, in case a local paper's layout team needs to rearrange the strip on the page.)
The last full Peanuts strip ran on February 6, 2000, which is the final appearance of Sally Brown and Charlie Brown's last starring role. It's a Valentine's Day strip, and as usual for Peanuts, it's about Charlie Brown wrestling with his own lack of romantic success.
Love's labors lost
In the last installment of one of Peanuts' sadder running gags, Charlie Brown is once again waiting outside his mailbox to see if he gets any love letters. Naturally, he doesn’t.
This time, he's making sure to scrub it down. "The inside of a mailbox should always be kept clean in case you get a love letter," Charlie Brown tells Sally, right before a sudden storm chases them both inside.
Once they're both dry, Charlie Brown continues to explain how these things work to Sally, including why he's not going out in the rain to check the mail again. "When it's raining, the only letters you get are those that say, 'I never want to see you again!'"
"You seem to know a lot about love letters," Sally says.
"If I ever got one," Charlie Brown says, "I don't know what I'd do."
If this wasn't so late in Peanuts' run, it'd just be another self-effacing strip about Charlie Brown's permanent losing streak. It's also another strip that runs off of one of Peanuts' core pillars, which is about how little kids will sometimes make up their own "rules" on the fly. Charlie Brown, Love Expert, is here to tell you how it all works. He doesn't actually know, but he sounds really certain.
There is a certain extra layer of pathos with this one, though. Charlie Brown leaves the world the way he came into it, doing his best to stay positive in a setting built around his misery.