The internet is filled with responsible advice on what to do if you’ve won the lottery. People say good stuff like don’t spend it all on stickers, stupid, and invest it for the long-term in a balanced basket of stocks, bonds, real estate, preferred shares, and other conservative investments. They advocate hiring smart people to help you out, especially if you’ve gone from rags to riches.

All of that is good, solid advice. Naturally we’re going to ignore all of it.

[Aside: people will tell you not to cash in the winning lottery ticket. They are morons.]

No, not really. But with the ol’ Powerball recently hitting $1.5 billion, I thought it might be fun to talk about the dumb stuff we’d all buy if we became billionaires.

But first let me crack out this picture, which is right up there next to the Mona Lisa as the greatest of all-time.

Y’know technically he’s not wrong.

Sure, we’d be responsible with our winnings. This would last about 14 seconds until we realized that $500 million invested at 4% gives us $54,794 to spend every single day. If I’m making a decent middle class salary every day you’re damned right I’m going to own 5,000 Playstation games. I’m doing my part to keep the economy rolling.

I wouldn’t just indulge in video games. Here are a few more things I’d buy.

New socks

Oh wow. Such a baller. 

Oh no, Italics Man. I wouldn’t just buy new socks once. I’d buy a year’s supply and crack out a new pair every morning. There is nothing that beats pulling on a new pair of socks for the first time. After my 12 hours of use I’d throw them at some hobo with dirty feet. Cover that up, man! Nobody wants to see stinky hobo feet.

Notice how underpants aren’t on the list. This is because they always take a few wears to get just right. That’s how the bastards at Fruit of the Loom get you.


Golf is so god dammed expensive I feel like I can’t responsibly partake in it without being at least a deca-millionaire. It’s like $100 to do 18 holes on a half decent course. $25 an hour is too expensive for entertainment. You can get the cost down if you join a course and buy a membership, but even that comes to like $3,000 a year on the low end. Screw that.

Maybe I’d build my own course if I was worth $500 million. It couldn’t take much more than $10 million to get it off the ground and another $500k annually to keep up. I have no idea. I’m just pulling these numbers out of my ass. Then I could invite all my readers to my personal course just to kick them out five minutes later for no reason. Fun!

Golf is the only rich guy sport I’d do. Polo is dumb and if I’m going onto a ship somebody else is driving it. I guess I could invite Prince Charles over and we could hunt some foxes. That’s a rich guy sport, right? We’d laugh and say “indubitably” a lot. Then I’d crack jokes about his hot daughters-in-law and it would be awkward.

Petty revenge

Every year I’d set aside a few hundred thou to get petty revenge on people who wronged me. Sorry for all the dog shit on your lawn, guy who once mocked me in high school. Sucks to be you, guy who once cut me off and now has his tires slashed. And so on.

Naturally, I’d hire someone to do the dirty work. It would all be so petty the cops wouldn’t stop me.

Five Guys everyday

I’d weigh 800 pounds and die at 50, but it would be worth it.

What outrageous shit would you guys do if money was no object? Tell me. I need to know. It consumes me.

Tell everyone, yo!