Just like the separation between church and state, there is an implied separation between the corporate work environment and emails containing salacious personal information or off-color jokes.There’s even an official acronym for it: NSFW (Not Safe For Work). Ironically, the most scandalous NSFW emails always seem to end up making the rounds at work anyway. And some of them are so spectacularly awful, so staggeringly unprofessional and inappropriate, that they transcend office gossip and become international phenomenons. Here are just a few of our favorite NSFW train wrecks from the last decade.

1) Korean Sexcapades

Like any 24-year old Princeton graduate worth his salt, Peter Chung had big ambitions. So when he landed an executive job with the Carlyle Group in Seoul, he knew he was on his way to achieving the dream of any upwardly mobile professional; having sexual relations with “every hot chick in Korea.” In an email with the subject line “LIVING LIKE A KING ,” inexplicably sent to eleven of his colleagues at Merrill Lynch in New York (his former employer), Chung boasted that the tally of his sexual conquests was “5 down, 1,000,000,000 left to go.” It doesn’t get much more romantic than that.

2) The Pentagon Shares Secrets With Their Teenage BFF

Everybody’s sent a work email to the wrong person at least once in their careers. But it’s rare to make that same mistake 250 times. It’s especially unfortunate if you work at the Pentagon, which has a reputation for being semi-good at keeping secrets. That’s what happened to Royal Navy Commander Jim Dale, who inadvertently sent hundreds of emails marked as “security restricted” (including a 64-page document about the importance of protecting sensitive information) to a 15 year old girl named Claire McDonald. When she tried to report the error and, in her words, “make (the emails) stop,” Commander Dale blamed the problem on her internet service provider.

3) Politicians Say the Darndest Racist Things

Comedy and email don’t often mix well together. How many times has an email joke backfired or a seemingly innocent NSFW one-liner offended a co-worker? But while 99% of these email jests have the best of intentions, there’s always the 1% that are just hostile and pigheaded, regardless of context. Florida Committeewoman Carol Carter probably thought she was being funny when she sent an email to dozens of her Republican colleagues, remarking on the African-Americans traveling to Washington, D.C. for Barack Obama’s inauguration. “How can 2,000,000 blacks get into Washington, DC in 1 day in subzero temps when 200,000 couldn’t get out of New Orleans in 85 degree temps with four days notice?” Carter wrote. Hurricane Katrina humor, get it? Yikes. Carter resigned shortly thereafter, but not before sending one more email, wondering if politicians would be “allowed to keep our sense of humor.” A sense of humor, sure. Racist ramblings, not so much.

4) “Yours Was Yum…”

It should go without saying that among the topics not suitable for a work email, an enthusiasm for a co-worker’s semen probably falls near or at the very top of the list. But nobody bothered to share this wisdom with Claire Swire, a former employee at London law firm Norton Rose, who decided that it was entirely reasonable to devote a working afternoon to composing an email sonnet about the magical viscous fluids of her then-boyfriend, lawyer Bradley Chiat. “I hadn’t swallowed in years but yours was yum and very good for me too,” she wrote. “Apparently it’s a very good conditioner for your hair too…getting a funny picture in my head…” Chiat was so flattered by the email that he felt “honour bound” (his words) to share it with friends and co-workers, who continued forwarding it until the happy couple’s private moment of yuckiness became a company-wide shared shudder of disgust.

5) On a Scale Of 1 To 10, They Get a 10 For Douchebaggery

If you’re a woman employed by PricewaterhouseCoopers, it’s only natural to expect that your male co-workers will be exchanging emails about you, secretly rating your attractiveness. Wait, no, the opposite of that. But that’s precisely what happened to thirteen female employees at a Dublin, Ireland branch of the prestigious accounting firm. As fresh recruits to the company — or, as they were described in an email chain among seventeen male PwC staff members, “new clunge” (“clunge” being a derogatory word for female genitals) — their headshots were evaluated using a “k-score” system that’s apparently a time-honored tradition among accounting douchebags. Their email debate somehow got into the wrong hands and went viral, and the company that once boasted on its website of having a global workforce that’s half female was suddenly forced to explain why the other half of their workforce appeared to be mouth-berating morons.

6) Chick Ham Fight!

Tempers at the office can flare up about the silliest of things. Just ask Katrina Nugent and Melinda Bird, once employed as legal secretaries at an Australia law firm. A simple misunderstanding about the location of a ham sandwich, which had mysteriously gone missing from an office fridge, quickly escalated into a heated email exchange — in which several co-workers were cc’d — that read like a hair-pulling, groin-kneeing fight between teenagers. Insults were hurled between Katrina and Melinda like grenades, including comments about blondes being stupid, the other person’s “figure” and who among them had the most high-paying job. Melinda effectively ended the email spat by writing “I have 5 guys at the moment! haha.” It’s unclear why her ill-advised sexual bragging brought the feud to a screeching halt, other than being so preposterous and weird that it forced both women to think out loud, “Oh dear god, what I am doing?”

7) Revenge Is a Dish Best Served Cold… in an Email To Your Ex-Husband’s Clients

If you’re going to be a terrible person and cheat on your wife, at least make sure she doesn’t have access to your email. That’s the hard lesson learned by PR manager Paul Evans, who purportedly had an affair that was discovered by his wife Tracey. Rather than just pack up her belongings and leave, she decided to have some fun at his expense. She hacked into his account and sent a scathing email to 50 of his business contacts, including executives at Volkswagen, informing them that he was a “sniveling, cheating, lying, arrogant little piece of shit. No, that’s not right — I’m worse than that: I’m a despicable, deceitful, dodgy, DICKHEAD who doesn’t reserve this attitude just for his wife.” Think it couldn’t get worse? Oh, it got so much worse. She went on to reveal that he has “an extremely small penis that couldn’t excite a woman’s nostril let alone anything else.” Needless to say, his marriage ended almost as quickly as his job.

8) All Caps Is How an Email YELLS AT YOU!!!

With all the complaints about tasteless jokes and pornographic photos being forwarded around the workplace, it’s easy to forget the most common offender: Over-enthusiastic capitalization. Vicki Walker, a financial controller with ProCare Health in Auckland, New Zealand, was fired after two years with the company for, according to ProCare, creating “disharmony in the workplace by using block capitals, bold typeface and red text in her emails.” She cried foul, and New Zealand’s Employment Relations Authority agreed with her, ordering ProCare to pay her $17,000 in New Zealand dollars (roughly $11,500 in U.S. dollars) for unfair dismissal. It ended up being a win-win for everybody: Walker got a hefty payday for email bigotry, and her co-workers never have to read another UNNECESSARILY COLORFUL EMAIL THAT’S SHOUTS AT THEM!!!

(This story originally appeared, in a slightly different form, in the January 20th, 2012 issue of Bloomberg Businessweek.)