Winter is usually fun for a little while, and then, after many months of no sunlight and cold weather, you're ready to jump off a bridge a la George Bailey in It's A Wonderful Life. But your winter is NOTHING compared to what these people have to deal with in winter. Unless you live in one of these places...in which case...good job.
8.) Winnipeg, Manitoba, Canada

"Don't you just love this spring weather?"
Winnipeg isn't AWFUL. It's actually pretty sunny in the winter. Regardless, the temperature is blisteringly cold from November to March. Also, have fun with the wind that blows hard off of Lake Winnipeg. Ouch.
7.) Sault Ste. Marie, Michigan

The beach in Sault Ste. Marie.
Are you ready for some fun in the sun? Then don't go to Sault Ste. Marie! You get to enjoy 180 days with weather UNDER 32ºf! Blah! There's also 200 cloudy days a year, most of them in winter.
6.) Ulan Bator, Mongolia

Ulan Bator: Picture taken during the annual 20 minutes that it isn't cold
This place is freezing! Their summer starts in June, peaks in July, and gets right back down to 40º in September. Winter is a barely noticeable -15 in January. It's the capital city of Mongolia, and over 1 million people live there for some reason!
5.) International Falls, Minnesota

Yes, that's a tree covered in two centimeters of ice.
International Falls is one of the coldest cities in the U.S. It's so cold, that in order to have something to do, the residents fought against Fraser, Colorado to win the title of "Icebox of the Nation." What a fun thing to do! If you live in International Falls, you get to experience winter temperatures often in the single digits or teens. Oh, and you get to say you live in the "Icebox of the Nation." You're so lucky!
4.) Yukon, Canada

Don't let the beauty fool you. It's freezing.
Mmm, the Yukon Territory! MORE LIKE TERROR-TORY. Sorry. Yukon gets brisk around September, and hits single digit temperatures soon after.
3.) Yakutsk, Russia

"Are my walls made of ice? Makes sense, I guess."
Yakutsk is generally recognized as one of the face-meltingly coldest places to live on Earth. But that's ok, because not that many people live there. Wrong. Yakutsk is inhabited by 210,000 people, which is an INCREASE from the population in 1989, which was 186,000. Hope you don't like basements, because Yakutsk sits on permafrost; ground that is permanently frozen. Get used to -45º temperatures in January in this lovely town. Whats that? It gets up to a blistering 77º in July? LET'S GO! Let's not go. That place sounds awful.
2.) Oymyakon, Russia

Oymyakon's sign post is their #1 tourist destination.
Let's just put it this way; Oymyakon's RECORD high temperature is 90ºF. That would be the HIGHEST RECORDED TEMPERATURE FOREVER. Even in July, Oymyakon only averages about 70º. The winter months average highs in the negative degrees fahrenheit. HIGH temperatures of around -9 in November. -41 in January. That's probably a lot of fun. "Hey kids, put on a scarf, it's -40 out." Never take a job in Oymyakon.
1.) Longyearbyen, Svalbard, Norway

This guy died in this exact spot 1945.
This is one of the weirdest places to live. And definitely the worst. Polar bear protection training begins at a very early age. And then when you get old you have to make some measures to make sure you get buried. Because if you die in Longyearbyen, you don't get buried. The ground is frozen, and authorities (they have that?) discovered that bodies weren't decomposing properly in the cold. "Hi, body transportation service? I will be dead in a few hours. Could you pick me up and fly my body to a place that allows burial? Thanks."
And possibly the worst part about it? Well, BESIDES the frozen corpses of your departed loved ones littering the ground, is the 6 months of perpetual darkness. Yep. Winter in Longyearbyen means the sun says "Fuck you!" and disappears. But of course, it also means the sun NEVER goes away in summer. It must be how parents of college kids feel. Around all summer, but we never call when we're away at school. And the sun never needs money, so don't expect it to pop in every once in a while.