Jon Rineman is a 2005 Emerson College graduate, and has been a regular at the Comedy Studio in Harvard Square since 2004. He is a freelance monologue writer for Jay Leno and was published in the 2005 humor edition of the Improper Bostonian. His weekly blog www.rinemania.com features news jokes and his signature comedy bit, Cause & Effect.

When did you first realize that you were uniquely funny?

Honestly, I'm still not sure that I am. As someone who's only twenty-five and still trying to break in as a writer, it's tough to claim unique funniness. I think I realized I had a unique ability when I started having my jokes published in the weekly Comedy Studio newsletter and stand-ups I look up to told me they could never write good, tight topical jokes on a daily basis — which makes us even, since I come up with about three usable stand-up bits a year.

Who do you think were your influences?

Jay Leno's the major influence. He's been the torchbearer of monologue jokes since Johnny Carson — the original monologue pioneer — hung 'em up. I can't imagine a better duty than standing on stage night after night at 11:30 and telling twenty-five or thirty jokes written that very day. I was a big Kevin Nealon and Norm MacDonald fan when they did Weekend Update on Saturday Night Live, and also admire Conan O'Brien, as he essentially taught himself — a born improv comic — how to do a good monologue. I've known one of his writers, Brian Kiley, since I was in college, and he has always been very supportive and influential.

Do you remember your first original joke?

My freshman year of college, I came up with this observation about living in downtown Boston: “In my neighborhood, nobody calls an ambulance — it just runs on a shuttle schedule.” I actually still use this joke when I perform, and it holds up. Thanks, Mayor Menino!

When did you realize that comedy was something that you had to do for a living?

When I left my job at a local news station and soon discovered there was nothing else for which I was qualified.

What was your first job in comedy writing or performance?

After I graduated from Emerson, I was back living at home with my parents. After a few months, nothing was working out and I was desperate, so I called my parents' friend Barry. He had grown up with Jay Leno and remained good friends with him. I asked if he could put in a word. Of course, this was a favor he was asked on a regular basis, so he was a bit reluctant (for my own good), but I told him that I had been writing monologue jokes all summer and he wound up writing a very, very helpful and positive recommendation that he mailed on a Saturday morning to Mr. Leno. That Monday night, at 11 p.m., I'm up in my bedroom — writing jokes, seriously — and my Dad comes into the room with the phone: “It's Jay Leno.” We had a really great talk, and a couple weeks later, I sold my first jokes.

What is the biggest difficulty you've encountered being a comedy writer?

Still, just selling jokes, getting stuff seen. It's a weird situation for me because what I do is so specific, and there's a lot of uncertainty in the late-night genre right now as far as hiring goes. A year from now, I could be a staffer, or I could be screwed. Who knows? The toughest thing is that there are a lot — a ton — of other comics who would kill to get a job as a staff writer, many with better credentials in comedy as stand-ups and performers. My challenge is to just try to be better at writing jokes. Just work as hard as I can to be better. It means a great deal of frustration, and a lot of sleepless/thankless days and nights, and a lot of confusion by others as to what the hell I'm doing with my life — but, it's all about getting better and making the jokes stronger.

Are there jokes that you do just for you?

I don't do any topical stuff when I do standup, so basically anything I think up that's an original, personal thought, I keep. I came up with a joke that went, “If Hillary gets elected; she'll refer to her husband Bill as her First Gentleman; meanwhile, Bill will continue to refer to Hillary as his Last Resort.” Nobody wanted it, so I kept it, and it wound up working pretty well for “older” crowds.

What is the most frustrating part about getting “known” in the industry?

Ask me once I am.

What are the differences between writing for yourself and writing for others?

Honestly, it's just the type of joke. To me, a monologue joke is a monologue joke — yes, you may shape it to fit the host, but a premise is a premise. You write a real setup, and follow it with a made-up punch line. Whereas in writing for myself, I tend to be more observational and conversational, as opposed to set-up/punch line. The news is great and it's what I spend most of my time writing jokes about, but as far as “writing” for myself, it's more a matter of collecting and organizing genuine, original personal thoughts into something cohesive.

What do you find exciting about comedy right now?

It's a great time for late night. You have guys switching shows, switching coasts, even switching networks. And clips from each show are popping up all around the Internet. What you're seeing is a really great fraternity of comics collectively carrying on where the likes of Carson (Johnny, not Daly) and Steve Allen left off. And, you're also seeing some great sitcoms like The Office, 30 Rock, and Family Guy sort of reinvent comedy much the way Seinfeld did when I was growing up. And how can you not be in awe of The Simpsons?

Where do you think the future of comedy is headed?

Who knows? I think people are starting to appreciate different kinds of comedy, and the thought process that goes into it. But it's all a cycle. After a while, people get tired of down-to-earth comedy and go for zany. After that gets old, they go for down-to-earth. The main thing is the growing incorporation of the news. Jon Stewart really got the ball rolling, along with Stephen Colbert, and I think that's allowed other late nighters to be a little more political and cultural instead of just making fun of Amy Winehouse. Though Wine-house is always funny.

As audiences are becoming more specific and more segmented, is that making your job easier or more difficult?

It makes it more difficult on the inside, I think. Writers are pretty hard on themselves and each other these days to be original. But it's never a bad thing to have open-minded audiences who can catch obscure stuff as well as the old standards.

What is the best thing about being a comedy writer?

Being a comedy writer has always appealed to me since you're basically being told to be a wise-ass. I was always that kid in school who wanted so badly to make fun of whatever the teacher was telling us. It was almost like being dissatisfied with what actually happened and wanting to improve it to make it funnier. When you write jokes, that's what you get to do.

Do you have any advice for other up-and-coming comedy writers?

Being that I am one, I'd rather just ask if they'd like to sublet my apartment.