Big Fish Q&A with Baltimore Boy & Gawker Wunderkind Ben Rosen

Baltimore native Ben Rosen, 26, serves as ad operations coordinator at online media juggernaut Gawker Media,whose eight websites combined — Gawker, Jezebel, Deadspin, Gizmodo, Lifehacker, Jalopnik, Kotaku, and io9 — get more monthly views than The New York Times. Rosen, also a dedicated standup comic (he was voted Baltimore Comedy Factory’s Funniest Person of 2010), graduated from the Park School in 2004, and later the College of Charleston with a business administration degree and a concentration in entrepreneurship. He now calls Williamsburg, Brooklyn, home.

At Gawker Media, Rosen works with two more Baltimoreans — look for their profiles later this summer in our series, Baltimore Boys of Gawker Media.

I talked to the funny young businessman about his work life, his standup life, the future of social media, and his all-important Baltimore roots.

What is your dream job title?

Standup comic/astronaut.

Down the line, is the progression of social media going to make us better social animals, more connected, communicative and compassionate, worse…or both?

It depends on what you mean by better. We’re able to share more of our lives with more people, but it’s no question that the art of conversation is dying. Drinks with friends in a biergarten will always trump lonely Facebook scrolling in a dark room. Still, you can’t pin the end of the human race solely on social technology. I blame the parents, the Republican Party, and Rick Astley’s dance moves.

What’s your favorite moment of the day? Why?

Easy. There’s a dog that starts howling from across the street at 5 p.m. every day. It embodies everything that I believe in. He is my patronus.

What’s your favorite thing to do in Baltimore? To tell people about?

I like you, Betsy, so here is the biggest secret in the history of Baltimore secrets. The Sip ‘n’ Bite fried crab cakes are the best in Baltimore. I’ll give your readers a few seconds to gather their minds from the floor. YES, that dumpy little 24-hour…gross house has the most delicious fried crab cakes in the world. If you eat anything else on that menu, you have no sense of self-preservation. I also haven’t found a better slice of pizza here in NY than the cheese-magic that is crafted at Hot Tomatoes in Fells Point.

Which (serious or comedic) writer or visionary person do you most admire?

All comics for me: Dave Chappelle, Chris Rock, Louis CK, Dave Attell, Brian Regan.

Favorite TV show?

“Community” — sadly Dan Harmon was fired, so that answer will probably change.

What is the hardest thing about doing stand-up?

Sadly, everyone thinks they’re funny. You’re not. My first week in New York, I went to Caroline’s, one of the most famous clubs in the world, and the Naked Cowboy was the surprise headliner. I was pissed. He got on stage and did a whole bunch of Naked Cowboy jokes like” “My mom said I look perfect…but my bum has a crack in it.”

The audience didn’t even throw him a charity laugh. So he went home, head hanging low, and hopefully boarded a one-way flight to Afghanistan. The point is that stand-up is much harder than you think it is. There’s no clear path to success, there are absolutely no rules, and you’re completely alone. That drives some people crazy. Comedy is viewed as a narrative on our culture, but I really think it’s a narrative on the narrator — written, edited, and performed by the narrator.

How/when do you develop material?

I’m always thinking of new jokes, but my focus has shifted a little since I started. At first, I would say almost anything as long as the end product was a big laugh. I’m hoping that my newest material can change the way people think. This is one of the only professions where people pay to hear your opinion, so if I could get someone to laugh and be a better person, it’s a big win. Clever writing will get you the laughter, but a strong concept will stick with the audience long after the show is over.

How did Baltimore shape/affect your sense of humor?

Baltimore is a city of extremes. In the city, we have “The Wire,” but in the county we have Deliverance. In the winter we have the Ravens, but in the summer we have the Orioles. Comedy is all about extremes. I’ve always gotten the impression that Baltimoreans know how to make fun of themselves. It’s not like in New York or LA where everyone is too busy sniffing their own toilet paper, we know when to tell folks to “give it a minute.”