1. Participate in a public pillow fight
For the past few years, a massive pillow fight breaks out in Union Square. Everyone is invited as long as they’re armed. The “urban playground” is now a pretty big movement, but the public pillow fight started in New York City, and its pillow fight is accordingly, the biggest, and… fluffiest.
2. Improv somewhere with Improv Everywhere
Improv Everywhere are now a world-famous improvisational troupe, who go around New York and either instigate improv acts that other people take part in, or do them wholly on their own. One of the most prominent and funniest is the “No Pants Subway Ride,” now a years-old tradition. This year, more than 500 people did it. It’s expectedly awesome (if a bit awkward).
3. Spontaneous musical performances
Surprisingly, one of the most common occurrences in New York City are impromptu concerts by some of the best musicians out there. Arcade Fire recently performed at random in Union Square, and Rufus Wainwright and Sean Lennon showed up to do a short performance a couple months ago at Occupy Wall Street in Zuccotti Park. Anywhere you go, you have to be prepared to rock out. And that’s certainly not a bad thing.
5. Run into your favorite celebrity
So many celebrities call New York City their home (or at least have a penthouse or two) that it’s nearly impossible not to run into one of your faves. Alec Baldwin, for example, is well-known for getting his Starbucks up at 68th Street on the Upper East Side.
6. Get a pic with the Naked Cowboy
I mean, what’s not to like in this situation? Probably among the most notable street performances—of the thousands—is the Naked Cowboy in Times Square. Dealing with Times Square can be tough, but he definitely makes it worth it.
7. Join a parade
Of the many parades that happen in New York all the time, the Puerto Rican Day Parade is probably the craziest (and thus, best) one. Thousands upon thousands of people show up, including celebrities, like Jennifer Lopez, who attended last year.
8. See Ryan Gosling break up a fight
As common as fights are in New York City, there are few people who actually step in to stop them. Fortunately, there’s people like Ryan Gosling running around, who’s definitely not into that. This past summer, he taught a couple guys a thing or two, and looked great doing it. If you’re lucky enough, he’ll break up a fight for you, too.
9. See a movie being filmed
Outside of LA, NYC is the place to go to accidentally get caught in the filming of the newest movie. Will Ferrell and Mark Wahlberg, for example, shot a scene from “The Other Guys” while at a Knicks game.
10. Overhear horrifying, funny things
Considering there’s an entire website dedicated to things people have overheard in New York, it’s worth just walking around for a day without listening to headphones. You’ll hear some of the funniest, and likely, most disturbing, things you’ve ever heard.