8. Boston, MA
New England Patriots
Have you ever walked through the Public Garden onto the cobblestone streets of Beacon Hill on a crisp fall day, and found a cannoli from Mike's that you didn't even realize you'd purchased hours before, and thought that you were in the greatest city in the world; the Hub, if you will, of the universe?
And then did you get hit in the head by a Sam Adams bottle thrown by a 320lb liquored-up dude wearing a Marchand jersey over a Welker jersey over a Foulke jersey over a Scalabrine jersey, who'd just gotten so fired up rattling off Deflategate conspiracy theories that he missed the last Red Line train to the Quincy Adams station, and thought that you might not care if this city burned to the ground? Then congratulations, you truly understand the ups and downs of the Boston experience.
7. San Francisco, CA
San Francisco 49ers
Though you can only permanently reside in the City by the Bay now if you've recently sold a farm-to-drone app to Facebook or have old Belarusian money you recently smuggled out of Minsk, the City of Cramped Calves is still undeniably beautiful and grand, even if the people hitting you with their Teslas as they work up programs to steal your dinner reservations are not.
6. New York, NY
New York Jets and New York Giants
New York is the city equivalent of one of those claw-crane machine hand games -- it has all these plush and fancy-looking things that look like they're available to everyone, and so you spend your money to go there and then you come to find out that ALL OF THE NICE STUFF IS ESSENTIALLY IMPOSSIBLE TO GET UNLESS YOU ARE ONE OF THE PEOPLE WHO ALREADY OWNS A CLAW-CRANE MACHINE BUSINESS. But you come so damn close to winning those prizes and they seem so attainable that you just keep pumping money into it. This usually goes on for people's entire 20s and early 30s, until they give up playing the machine and move to Jersey to eat tomato pies in peace.
But in all seriousness, there's a feeling that goes along with being in New York that just isn't replicable anywhere else. It's almost like a country unto itself, which makes comparing it to other places extremely difficult. Kind of like safely handling fireworks. Sorry, JPP.
5. Chicago, IL
Driving (or biking or walking, if you're not in an Italian beef coma) down Lakeshore Dr, with the majestic skyline on one side and Lake Michigan extending all the way to the horizon on the other, is one of the finest damn sights you'll experience anywhere. Culinarily, Chicago measures itself against the world's restaurant capitals, which makes it all the more laughable when someone from New York turns out another condescending "guess what, Chicago actually has good places to eat that aren't steakhouses!" article. Also, literally every single famous funny person you know went to Chicago to learn how to be funnier.
Look! Got through that whole damn thing without mentioning deep dish once. Whoops. Shit. Well, you knew it was coming. Kind of like a Jay Cutler interception at a critical moment in the fourth quarter.
4. Denver, CO
Ah, Denver! Breathe in that fresh mountain air with just a hint of cannabis and green chile. Drink in the hoppy splendor of a craft beer scene that was bustling back when everyone still called them "microbreweries." Tolerate the alarmingly in-shape bro who stuck around after four years at Boulder to work as a part-time ski instructor and won't stop talking to you about fourteeners. Denver often gets championed for all the fantastic stuff to do right outside the city, what with the skiing and the hiking and the Red Rocks, but that does a disservice to all the good times to be had in Denver proper. The fact that said times can be had with herbal enhancement with nary a legal concern is just a bonus.