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What It Takes to Write ‘The Tonight Show’ (And The Writers’ 5 Favorite Sketches)

Supervising writer Gerard Bradford reveals just how much hard work — and random inspiration — goes into crafting the fun of the show.

Jimmy Fallon and President Barack Obama on "The Tonight Show."

Jimmy Fallon and President Barack Obama on “The Tonight Show.”

Andrew Lipovsky/NBC

To appreciate how much work goes into writing a show like “The Tonight Show Starring Jimmy Fallon,” ask a writer how many jokes they must write on any given day for any given segment. The answer is easily dozens, and that doesn’t include comedy pitches for celebrity guests and big sketch ideas like the show’s famed TV show parodies.

Gerard Bradford, a supervising writer for “Tonight Show,” broke down for IndieWire just how intense the production process can be. He also revealed some of his favorite sketches from the past year, and their more unusual inspirations.

What does having a regular schedule for specific desk bits like “Thank You Notes” mean for the rhythm of writing the show? 

It definitely helps – especially on a show like ours where we’re doing five hour-long shows a week, and each show can be very different content-wise on any given day. It’s a fun and crazy schedule and we wouldn’t have it any other way, but it’s nice to be able to look at the week coming up and say, “Okay, Tuesday is Pros & Cons, Thursday is Hashtags, and Friday is Thank You Notes.” They are sort of our “rock” in that way, and they allow us to really concentrate on the rest of the show that needs to be filled on those days and others.

When it comes to pitching ideas for celebrity guests, what do you and the staff find toughest about the process? 

I wouldn’t say it’s “tough” in terms of writing, because there’s not much downside to getting to write for anyone from Robert DeNiro to Ariana Grande to the President on any given day. It’s a gigantic part of our show. There are disappointments when you have an idea that you love and a celebrity doesn’t quite see it the same way you do. But regardless of how often it happens or doesn’t, there’s always a show to do the next day and we don’t have the luxury of dwelling on those types of situations, which is a good thing.

When picking a TV show to celebrate via “comedic homage,” what are the factors that matter most?

There’s no scientific approach to how we decide which shows we’re going to do our “Tonight Show” version of. We all ask ourselves the same questions: What shows are popular right now? What shows are people watching? What shows do we like watching? And of course, what shows appeal to Jimmy. What is he into and excited about? It takes a lot of time and energy — on top of the show we put on every night — to create these pieces, because of the love that goes into them and the attention to detail our staff and crew pays to them. So we want to make sure we’re all 100 percent into the idea from the start.

And now, Bradford’s favorite five sketches (and why)…

“Two James Taylors on a Seesaw”

“Music and songs have always played a huge part on our show, going all the way back to the beginning of ‘Late Night.’ Jimmy is a big music fan, and any time we book someone like Bruce Springsteen or Neil Young or Paul McCartney, we always try to think of something fun and musical that Jimmy can do with them. So when James Taylor was coming on the show, the writers were pitching a bunch of ideas and Jimmy just randomly out of nowhere said, ‘How about Two James Taylors on a Seesaw?’ He started singing the melody and first few lines of the song off the top of his head — just working it out on the spot — and then one of our writers, Mike DiCenzo, took that and wrote the rest of the song that night.

“What I love most about this piece is that it’s a very true representation of Jimmy’s sensibilities and instincts. The ideas that spring from his mind don’t come from a place of snark or cynicism. They’re very often like this one: sweet and silly and beautiful and ridiculous and smart and goofy all at the same time.”

“Tight Pants”

“This is another weird, random idea that Jimmy came up with. For a few weeks he’d been singing this little tune around the office, ‘Everybody’s talkin’ ‘bout my tight pants, I got my tight pants, I got my tight pants on…’ It was really catchy and we all really liked it, and Jimmy thought it would be a fun thing to do with Will Ferrell. So Mike DiCenzo and I took his idea and crafted a song and sketch out of it.

“‘Tight Pants’ is one of those bits that seems to connect with people of all ages. I’ve had many parents come up to me telling me how their kids love singing the song, and now they can’t get it out of their heads. It’s great. And Will Ferrell is just the best person to work with. Like Jimmy, he’s very funny, very friendly, and very understanding of writers and appreciative and trusting of what they do. Adam Sandler is very much like that, as well. Maybe it’s a ‘SNL’ thing? It’s always great to have that kind of trust from talented people you admire.”

“Thank You Notes”/”Pros & Cons”

“From the very beginning, it was always important to Jimmy that we have a signature, recurring comedy piece on the show, and ‘Thank You Notes’ became that bit. We do it every Friday, while ‘Pros & Cons’ is our weekly Tuesday piece. Both are very much a group effort, with the entire staff contributing hundreds of jokes every week to each piece – eventually getting whittled down to the eight or so that make it to air. I’m extremely proud of ‘Pros & Cons’ and ‘Thank You Notes’ because of what they are and what they showcase from our writing staff: simple, old-school joke telling.”

“Jimpire”

“Jimmy loves TV, and loves doing these types of spoofs of shows — although we prefer to think of them more as “comedic homages,” as we’re more interested in celebrating the show, rather than making fun of it. Over the years we’ve done our take on ‘Game of Thrones,’ ‘Breaking Bad,’ ‘Lost’ and ‘The Real Housewives,’ among others. It’s always fun trying to figure out a way to take the elements of a popular TV program and make them fit into our ‘Tonight Show’ world.

“These types of pieces are a fantastic showcase of our amazingly talented writer/director Dan Opsal and all of our production staff and crew, from hair and makeup to wardrobe to lighting to props. It sounds cliché, but they really are the best in the business. The love that goes into the making of pieces like ‘Jimpire,’ the attention to detail, and the look of the final product is something we all take pride in. It’s a lot of hard work and long hours, but it’s well worth it.”

“Slow Jam the News” with President Obama

“‘Slow Jam’ is our longest-running piece, and this was the second time we’d done it with the President, the first being in 2012. We love writing political sketches on the show, and politicians are very often eager to take part in bits with us. Over the years we’ve done sketches with Hillary Clinton, Donald Trump, Bernie Sanders, Ted Cruz, Chris Christie, and Mitt Romney, to name a few. We’ve always tried to make ‘The Tonight Show’ a friendly environment for political figures. We make fun of Democrats and Republicans equally. And I think politicians enjoy coming on our show and doing bits because they know that we’re there to make sure they have a good time and above all, look funny.

“And President Obama is no exception. He was really funny, really friendly, and he couldn’t have been easier to work with. I’ll always remember when were showing him rehearsal footage of the piece backstage before the show; there’s one part in ‘Slow Jam’ that called for him to sing Rihanna’s ‘Work, work, work, work, work’ line. In rehearsal it was done with a very dry delivery. The President saw it and said, ‘C’mon! Why do you have to make me look dorky? How about I do some moves like Drake?’ – and he started joking around with Jimmy, doing a dance. It was hilarious. It’s not every day you get to not only meet, but write for the President of the United States, and then share a few laughs on top of that. As writers, our days are long and busy, and often we don’t have the time to take a step back and appreciate what we get to do on a daily basis. ‘Slow Jam’ was a great reminder of how lucky we all are.”

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