The worst Bill Gates ever did was create Windows 98. But time healed those wounds, and he has done much since to undo the stigma. Like starting a mammoth philanthropic organisation and going all-out to try and end malaria, for example.

But there are an indecent number of people who’ve racked up the big nine-zero bank account for lives spent becoming masters of sin. The kinds of people who would make an unrepentant mortgage broker look cleaner than the Pope the morning after laundry day at the Vatican. Here are 5 of the worst.

Gina Rinehart

Estimated wealth: $17Bn
Made by: Being born. The world needing iron.

Rinehart, one of the world’s richest women, famously told critics of her wealth that they should “spend less time drinking or smoking and socialising, and more time working.” Which is ironic, given that she became obscenely wealthy herself via the Paris Hilton approach of simply being born with a silver spoon (or, more accurately, an iron mine) in her mouth. Born to Australian tycoon Lang Hancock in 1954, the uptick in global minerals prices in recent years saw her wealth ballooning to the degree that, at one point, she was effectively earning a million Australian dollars in the amount of time it would take you to watch an episode of Community.

The affinity that the obscenely wealthy have for Ayn Rand-esque ideas towards their fellow man (which is to say, complete loathing) is well illustrated by Rinehart’s argument in 2012 that Australia was becoming uncompetitive because countries in Africa could pay their miners $2 a day. The BBC estimated at the time that she was earning $600 per second during the recording of her speech. Which would make the excerpt below worth $31,800, or 15,900 such African labour days.

She also previously looked into the feasibility of using an atom bomb to create a harbour on the coast of Australia, or as a means of more efficiently mining. Because such a plan is not — of course — obviously insane at first glance.

Harold Simmons

Estimated Wealth: $8.5Bn
Made by: A bunch of things. Most pertinently, by storing nuclear waste badly.

If Gina Rinehart is a fan of detonating nukes, Simmons is a fan of using nuclear material to slowly poison West Texas. After six years of lobbying, the nuclear waste dump he opened in Andrews County, near the New Mexico border, collects low-level (that’s a euphemism) nuclear waste and stores it right on top of a number of large aquifers. One of which lies only 14 feet below refuse from nuclear medicine, old reactor parts, and radioactive weapons scraps. Some people get employed, Simmons makes millions, and liability when the water in Texas begins to glow lies with the state. Little wonder that Dallas’ D Magazine called him the city’s “most evil genius.”

It’s nice to know that the serious problems are being tackled by responsible, disinterested samaritans. I’ll bring bottled water on my next trip to West Texas, thanks.

Ivan Glasenberg

Personal Wealth: over $6.5Bn
Made by: Righteously screwing the treasuries of some of the world’s poorest nations

People who talk about the ineffectiveness of foreign aid to Africa routinely yap on about how ‘the Africans’ just cannot manage the however-many billions of dollars charitable folks from the West gave them this last financial year. Occasionally, ex-Goldman Sachs employees write such patronising arguments into books that sell a lot to the kinds of people who would prefer to buy from Africa what they couldn’t steal a century or so back, rather than concern themselves with properly understanding why net flows of money from countries like Zambia, for example, do not simply resemble mountains of cash squandered by inept Africans.

They don’t look too closely at capital flows out of many African nations precisely because you would end up finding companies like Anglo-Swiss Glencore and its boss, Ivan Glasenberg, at the forefront of using tax loopholes to screw weak nations out of tax revenue on their minerals. Glencore mines, say, iron from mines in Zambia and then sells it to a Swiss subsidiary at something criminal, like (for illustrative purposes) a dollar a ton. Which is to say well under the world market price. The company then pays its taxes on that dollar — which is, to say, a pittance. And the Swiss buyer can then mark it up to real-world prices and sell it wherever, paying little to no tax in the place in which the company (as a ‘trader’ of minerals) is domiciled. Zambia has most of the value of its minerals stolen, Glencore and Glasenberg makes a fortune.

Wash, rinse, and repeat on what is literally an industrial scale, and you’re responsible for occasionally stealing as much or more value from African economies than they’re receiving from aid. If it were possible to kick poor countries in their economic nuts, Glencore would be the steel- (or copper-, in Zambia’s case) tipped boot. So damaging is Glencore’s pursuit of this tactic that it was actually made the subject of an episode of Why Poverty on the BBC.

Dan Gertler

Estimated wealth: at least $2.5Bn, according to the Bloomberg Billionaires Index
Made by: Selling the diamonds nobody with a conscience would sell

Are you an undemocratic African leader? Have you found yourself recently in charge of a large nation with criminally rich diamond deposits, but have trouble convincing investors to get involved in extracting the wealth and paying to keep your corrupt and gargantuan administration from utterly unraveling?

If so, then Mr. Gertler may be just the man to bankroll your regime. For the unbeatable price of pissing away your mineral rights.

A personal friend of Joseph Kabila, the election-rigging leader of the Democratic Republic of Congo, Gertler has had a long, lucrative, and unpleasant ride to riches off the minerals of what may quite possibly be the continent’s most exploited country. When Joseph’s father, Laurent Kabila, was waging the first Congo war in 1997 that would kill almost a million civilians, and essentially constitute a retributive genocide against those who had fled Rwanda after 1994, it was $20 million from Gertler in exchange for exclusive rights to Congo’s diamonds that would help to fund the killing.

In 2011, the International Monetary Fund asked a pair of major mines in the DRC to explain the unpublicised sale of assets to companies linked to Gertler at below market rate, which were then sold on for hundreds of millions in profit. In 2012, the Eurasian Natural Resources Corporation spent around half a billion dollars to divest from its ties to Gertler, accused of “looting Congo at the expense of its people.”

Looting Africa wasn’t just the favourite pastime of genocidal Belgians, or abusive alcoholics in pith helmets. It’s carried out as a lucrative modern trade in diamonds and copper by companies like Gertler’s.

Viktor Bout

Estimated wealth: Around $6bn
Made by: Selling stockpiles of small arms to nasty people all over the world, on behalf of nastier people who can’t be caught doing it themselves

Remember that heartwarming hollywood film about a small-town boy who makes it big trading conscience-crushing volumes of small arms to people in West Africa? Yes, Lord of War. Which, as it happens, was largely inspired by the antics of Mr. Bout — except that the real-life story appears to have had little of the moral reflection or final escape from jail that Nicolas Cage enjoyed.

Viktor Anatolyevich Bout was possibly born in Tajikistan, possibly in 1967, and is said to be a polyglot — speaking six languages that include Persian and Esperanto (yes, Esperanto) from age 12. After working as a translator in the Soviet Army until 1991, Bout would go on to run ‘air freight’ (as in, not really) to Afghanistan, Sierra Leone, Congo, Kenya, Lebanon, Libya, the Central African Republic, and Angola. That air freight would be used to try and shoot down airliners, prolong wars, and generally foment truly revolting amounts of pain across the world. If there was a group, or a war, that no sanely ethical individual would sell weapons to, Bout apparently would. Y’know — supply and demand.

Arrested in Bangkok in 2008 for trying to sell weapons to people he thought were FARC rebels, but whose business cards actually said “DEA,” Bout is now serving 25 years in jail in the US, because public gelding was not an option. To the horror of the Russian government and doubtless a bunch of other people whose numbers were probably in his rolodex. That also makes him the only member of this evil billionaires club to actually find themselves in jail.

So there. Hollywood doesn’t always lie. There really are people that bad.