Jon Rineman is a multi-talented funnyman. People might know his name from his job as a monologue writer at Late Night with Jimmy Fallon, and he also performs stand-up. Rineman might have a dream career now, but he worked incredibly hard to get to the writer's table. He shared his job-hunting experiences with me as well as filling me in on his very different processes for writing for Late Night and his own stand-up.

Times Square (TS): Was comedy a part of your upbringing?

Jon Rineman (JR): It was. I think like a lot of people, my parents influenced me. It's interesting; my dad is a very nice guy, not the most outwardly funny guy, but a big fan of comedy. He got me into Leslie Nielsen, Cheers, and Bob Newhart. I got into comedy a lot from watching T.V. My mom was never a huge watcher of comedy, but I think I get that sense of humor from her. She has a very dark sense of humor—not a lot of people know that about her because a very nice lady and is kind to everyone.

When you get to know her, it comes out. It's showing up on Facebook a bit. I'll post something there, and then she'll put a joke. Sometimes I have to delete it and tell her that everyone can see the inside joke she wrote! So I think I got it from them: my dad loves comedy and my mom is very funny. I think like most kids it was an attention-grabbing thing. It became a cool thing—showing off for people. But, there's a science to it. There's a challenge. Whenever I had a school presentation or anything like that, it was neat because I had to show that I learned something, but I could also make it funny. I think that's what comedy is! You're talking to people about actual things and making a point, and the challenge is making it funny.

TS: How did you get the job writing for Jimmy Fallon?

JR: Prostitution! No...I used to be a freelance writer for the Tonight Show with Jay Leno, and I also did the same thing for Seth Meyers. Summer of 2009, I was really close to giving up. I had never gotten a staff job at a show even though I had a good amount of jokes on the air. I didn't have anyone to write for that summer, and it didn't account for the income I'd be losing if I just stopped all the sudden. I emailed Wayne Federman, who was the head monologue writer at late night at the time. I asked if I could send jokes for a couple of months. About a month and a half in, I got an email asking if I wanted to interview for a staff job.

I came down, and it was Jimmy, Wayne, Mike Shoemaker, and Gavin Purcell. It was a very quirky interview, but they liked me and I got the job! There was a year I spent working—I knew that Conan O'Brien was going to be moving—I had a friend that worked there and told me they'd be looking for writers, so I spent that year just being dedicated. In addition to sending jokes to Jay every day, I really tried to make them good. I'd read everyone's monologues. It had really gotten to the point where I really needed a job, and that's when everything worked. It was at the last minute that everything worked out.

TS: Is your approach to writing stand-up different than writing jokes or sketches?

JR: I write monologue jokes, so it's very different. I don't like to sit down and write a joke for stand-up. That's why I have respect for people who are full-time comedians. I have huge respect for people like Jim Gaffigan and Greg Giraldo (who I got to know before he passed away). They are/were prolific writers. I just couldn't [plan in advance]. It's stereotypical, but if something bugs me, that's when I make bullet points. I fill it in as I tell it. I got married last year, and even talking to my wife or my friends, someone will say something and I'll say something back. And they'll say "Oh! What a good joke!"

The truth is, it's not a joke. My wife really did ask me one time "If I died, how fast would you have sex with someone else?" I said, "At the same speed you and I have sex!" It's really what I said, and it's a great joke that works great in a set. That's what I'll do for stand-up, I'll react to something. Monologue jokes are totally different because you have to sit down; there's not another way. You're at the batting cage: here comes another story, what are you going to do? You just have to keep going. So stand-up is a lot looser and more natural. Monologue jokes, you have to do a lot more of everything. You have to get a pulse and feel for what everyone thinks about a certain issue. That's more of the assignment. With stand-up, it's up to you.

TS: What does the rest of the summer look like for you?

JR: I do have something pretty exciting in the works. I hate when comedians say that, "Oh I might have something really big," and I'm thinking a sandwich at home? But I do have something I can't say a whole lot about, but it's very cool. I'm still at the show and doing well there, and still doing stand-up. I'm going back home to New Hampshire and doing a show up there. I'm doing stuff in Boston and at that new casino here in New York. I'm really excited about Caroline's! I was really happy to hear about that offer. It's like a dream come true!

TS: On a day-to-day basis, what makes you laugh?

JR: I'll be honest: YouTube! It's still a thing for me. I still laugh when I see the jet ski guy that doesn't take off and falls into the water. But, I work in a funny place—it's Fallon! There's so much ridiculousness. Work makes me laugh.

Jon Rineman is at Caroline's on Broadway Tuesday, July 31st. For info and tickets, please visit http://www.carolines.com/comedian/breakout-artist-comedy-series-jon-rineman/

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