The only thing I’d do is get a video of my upcoming wedding (he’s black, I’m white) and send it to every member of my late husband’s raging racist asshole family. That would amuse me.
On the other hand, I could afford to do that now, but I’m too lazy.
I thought about this…and came up with nothing. Nothing outright mean. Sure, I have causes I care about, but I don’t think opening up an inner city school for kids is MEAN.
Well, you could buy or build a huge billboard directly across from their house ($50 billion can buy a lot of zoning variances) and with the new electronic billboards, it can play your wedding video 24/7.
Hell you could probably play your wedding night video once or twice. Five figure fines? Pfft.
Buy the Miami Heat. Dissolve everything except for the Lebron James contract, which I would sell to Cleveland for one dollar.
I’d buy a fleet of lovingly restored 1971 Ford F100s. Red, 300 in-line 6, with 4 on the floor.
And then I’d drive. Obeying all traffic laws and all normal courtesies of the road. I’d keep right except when passing, move to the left to allow a merge when possible, and make reasonable accommodation to the necessity of other drivers.
And when someone with a yield sign tries to force over, when someone races ahead of everyone else in the lane to merge, when someone tries a California turn… Well, I’ll stay right where I’m at/move to where I’m moving. I’d call their entitled bluffs, every time.
I probably wouldn’t have insurance, either, beyond the state minimum. Oh, and I’d have the best lawyer possible on retainer for any tort claims.
Petty, sure. But man it’d be fun.
It can be, if you buy several offices in a ritzy high-class office building and convert them into classrooms. Preferably right next to a CEO’s offices. 
Along those lines, I would buy the Sears tower. I would do whatever it took to relocate the people and businesses currently renting them–pay a business a few million plus relocation fees to an adjacent city, and they’re likely to go along with whatever I tell them to. I’d pretend to be a mysterious philanthropist. Then I’d demolish the tower and build new low-income/no-income housing (think Cabrini Green, but with better security). I’d bring all the city’s homeless under one enormous property-value-lowering roof.
I would also start secretly turning Lake Michigan red. Lots and lots of people with lots and lots of Kool-aid powder? I don’t know. But it will be done.
I would buy up a lot of ad time on television that portray gay people as loving, caring individuals who deserve respect, that equal marriage is the only marriage, and that it’s ok for kids to know about gay people existing, and even to learn about gay historical figures in positive ways. That is sure to piss off a lot of people.
And it would be done in spite, against all the homophobes I hate 
I want the people in the white house next to me to take their noisy, stupid, wretched hounds and get the fuck out of this neighborhood. It would be worth whatever it costs.
I also like ***ballardfam’s *** idea. I’d spend time telling some people that I wouldn’t give them a cold and fuck off.
[ol]
[li]Buy every Disney world and Disneyland as well as the movie rights to the entire collection.[/li][li]Show 2 Disney Movies on all major networks after school every single day.[/li][li]Every commercial during the movies would be a spectacularly beautiful and well made ad for the Disney parks.[/li][li]Raise the entrance fee for the parks to astronomical levels, beyond the means of 99.99999% of households so that completely indoctrinated children will never be able to actually set foot in the parks and will beg their parents mercilessly.[/li][/ol]
Open a Giant “super computer mart” across the street from Best Buy selling decent workable windows machines for $300 each including onsite delivery and setup. USB and HDMI cables are free with any peripheral or monitor purchase.
Then wander into the store offering employees there triple their normal days wage to call in sick on a random day each month.
I would first buy the high school my husband went to and let him burn it to the ground. It wouldn’t really hurt anybody, granted, but it’d make him feel a hell of a lot better.
I would also find a way to financially destroy a company that my mom worked for that fucked her over royally. They’re only worth 2-3 billion so it shouldn’t be too hard. I’d also personally ruin the guy responsible for the whole thing (now working for another company) and I’d make sure he knew why it happened to him and who was behind it. Hell I’d ruin his life now if I had the means and opportunity - don’t get me wrong, I’m no murderer - I’d never physically harm him, just make him wish he was dead.
But … that would be wrong. sigh Still kinda fun to think about though.
Part 3: Hunt down the asshat responsible for the cancellation of Firefly and make sure he never works at a job more advanced than fast food toilet cleaner for the rest of his miserable life.
Buy every soccer ball, goal and jersey in the country. Burn them all.
I would be so busy having fun I wouldn’t even think about spite!
Although it would be tempting to force my father into a nursing home where they neglect him and occasionally wave food in front of his face without feeding him for a day or so. Nothing too abusive. Nothing like sexually assaulting him or anything. I’m not nearly as cruel as he is.
I would buy all of the large, dilapadated buildings in Detroit that the media always shows when they have yet another story about Detroit being a hole. I would knock them all over just so they would have to find other buildings to film.
Dump my druggie cousin in the middle of rural China with $100 and let him figure out how to get back. Just so he won’t bother anyone in the family for a while.
Burn a couple of old bosses’ homes flat and make them dependent on the kindness of others. Just maybe they’ll learn something about gratitude. Humility at the very least.
With that out of the way, I think we’ll move to a snotty suburb, so my husband can sun hisself in his boxers and scratch his butt a lot. In the front yard.
I would put a bounty on every religious right public figure in existence. Find evidence of them behaving in a manner contrary to their declared beliefs - a ‘pro-lifer’ getting an abortion, an anti-gay rights advocate soliciting gay sex, a ‘family values’ proponent cheating on his spouse, an anti-pornography spokesperson downloading porn - or otherwise despicable or illegal acts.
If the evidence is confirmed by my independent investigative service (all of them gay porn stars who do volunteer work at Planned Parenthood), then it is publicized and/or handed over to the authorities for appropriate prosecution. The person who submits the evidence is given a big chunk of cash.
Every time one of them has to resign, face a divorce, explain their choice of bed bunny, be removed from office, go to rehab, declare bankruptcy, stand to hear their sentence read, or cry at a press conference, I throw a big, happy, ‘fuck you’ party, and everybody gets noise makers.
I’d buy Spiderman #1 and Superman #1, then eat the Spiderman comic in front of the comic book guy, and wipe my ass with the superman comic. Also right in front of him.
I would sue anyone who had ever crossed me until they were destitute. I would go full on Goldman-OJ-white-whale sue happy. This also includes annoying companies like PETA and Greenpeace, and morons who protest things like nuclear power. I’d also keep the Westboro people pretty busy. What do I care, I have $50 billion, they’ll go broke before I do. Now, this doesn’t mean people that cut me off in traffic or didn’t approve my loan, I mean people like the kid’s mom’s family, who are all batshit crazy and I lost everything I had due to legal battles. My old boss, who when he found out I’d been arrested (by the previously mentioned batshit crazy family) and I’d lost my house and family due to impending divorce, proceeded to gleefully fire me for not calling in. I’d have him lucky to be living under a bridge drinking hobo’s pee for a little alcohol.
I’d build me my very own Tenpenny tower, and have one of these babies on the top floor. No one gets to live in it but me, even though there’ll be thousands of rooms. Then I’ll just aim the ADS around at random and shoot people with it, only instead of microwaving people I’ll have it augmented so I can whisper things at people. Then I’ll microwave them.
I’ll drive around a HumVee (complete with .50 cal mount on the back) and paint it garish yellow. Anytime I see someone who’s parked like an asshole I’ll use that fucker to squeeze in next to them. If it happens to rip their car in half longitudinally, oh well. I should probably get a bulk discount with the government.
For a hobby to pass the time I’ll run for some kind of office. I’m not even remotely qualified, but that doesn’t stop most people. I’ll appear to be the most corrupt, bribable official who’ll hobknob with lobbyists, contractors, cronys and high powered businessmen. Then once I have their money do whatever I want anyway, fuck their opinions.
And I’d make a sex tape.
HubZilla, you done stealed my idea. But it’s a good one, so that’s okay. Just want it on the record that I won the internet years before you did. 
That’s where I got it from. Your legacy will live on!
I’d rename two baseball teams. The New York Red Sox and the Boston Yankees. I’d be being mean to myself, but that would be the ultimate meanness.
I would find every possible football recruit for the University of Notre Dame and pay them $10 million to NOT play for Notre Dame. I would then tell the University that I would stop doing that if and only if they agreed to publicly beg the Big Ten to let them into the conference. I would then buy the Big Ten and make Notre Dame jump through humiliating hoops for years while pretending to consider letting them in, all the while only allowing the worst possible players to sign with Notre Dame. Finally, I would bribe every possible advertiser to boycott NBC, unless NBC agrees to continue broadcasting every single Notre Dame game, nationally, coast to coast. Rinse and repeat . . . . .