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by Dan Snierson

Photographs by Art Streiber

He’s great at getting people’s secrets, so we went after his own. Get ready for a no-holds-barred oral history of the talk-show host from the people who know him best.

Featuring Ben Affleck Sarah Silverman Jimmy's Parents Lena Dunham His Childhood Priest And More

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Jimmy Kimmel is exactly who you think he is. Jimmy Kimmel is nothing like you think he is. Spend an hour or two chatting with the leaned-down 47-year-old host of ABC’s Jimmy Kimmel Live! (“On Mondays and Thursdays, I don’t eat,” he deadpans) in his artifact-stacked office above Hollywood Boulevard (notice: an ESPY award that he swiped from ESPN, a blanket with a picture of Michael Jackson’s son Blanket on it, an R. Crumb drawing of a banjo player on the back of a menu, three clarinets) and you will glean a portrait of a hard-driven, impish guy who actually might be the sharpest knife in the booby-trapped drawer. You’re probably already familiar with the bio basics. Raised in Brooklyn and Las Vegas. Began his career on the radio as a morning-drive DJ and KROQ's wise-ass Jimmy the Sports Guy. Co-hosted two Comedy Central series, Win Ben Stein’s Money and The Man Show. Launched his ABC late-night talk show in 2003 to rocky ratings, but with swift-of-foot wit, crafty bits like “Unnecessary Censorship” and “Mean Tweets” and devilish pranks like “I Told My Kids I Ate All Their Halloween Candy” and “Worst Twerk fail EVER”, eventually turned JKL, which now airs at 11:35 pm, into a Nielsen contender (it’s the no. 2 broadcast late-night talk show among 18-to-49-year-olds) and viral epidemic (2.6 billion views on his YouTube channel). Talk to the people who knew Kimmel as a little kid or a big kidder, though, and you’ll see that there are many more dimensions to the perpetually moving entertainer. (After playing host to President Obama last week, he’s currently staging a week of shows in Austin.) Did you know that he’s a chef who makes his own vinegar, an artist who sketches people in meetings, and a comedian who’s maddeningly relentless in bullet-proofing a joke? Below, we bring you revealing tales from some of the folks closest to Kimmel—his parents, his wife, his childhood priest, Ben Affleck—and then let him have the last word.

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The Early Years

Explosive Altar Boy With
An Artistic Side
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Jim and Joan Kimmel

Jim and Joan Kimmel

Jimmy's parents

Joan Kimmel He’s a brilliant artist. He sketches. He gets the essence of the thing or person he’s characterizing. We have a really nice charcoal drawing hung in our house of a Bakuba Tribesman. It was a photograph he’d seen in a National Geographic magazine of this tribesman sitting in a throne, and he did the whole thing in charcoal and it’s fantastic. It was in a school art exhibit and a gentleman loved it so much he wanted to buy it, but we were like, “No, no, no—this stays with us.”

Drawing by Kimmel

JIM KIMMEL He was so talented. I really thought he was going to be an animator. I think one of his teachers had gone to the California Institute of the Arts, and that was something we were looking into. It would’ve been interesting if he became an animator for Disney.

JOAN KIMMEL Well, he decided to work for Disney anyway.... I saw him pairing his wit with being an editorial cartoonist. He always had that left of center view of things. If the rest of us are looking at a problem with ecology, he’s looking at it as a torrential tsunami of melted icebergs. I just imagined that that would be his career path. And then he fell in love with Letterman and radio. [There was] a competition in Las Vegas—people sent in tapes of themselves to a popular radio station, and Jimmy won. When they went to meet him, they found out he was 16 and he couldn’t win. You had to be 18 because it was a position on the radio.

JIMMY RESPONDS When I was a younger kid I liked comic books. I always gravitated toward drawing funny things. Maybe I would have done political cartoons or something. I did do a little of that when I was a kid because I’d see them. I’d draw the presidents but I was never great at it. Mostly what I was good at was drawing grotesque caricatures of my friends and teachers. That’s where I really shine and it still goes on… I always thought I’d be an artist, but I started watching late-night television while I was drawing. I’d watch Johnny [Carson] and then Dave [Letterman] and then NBC News Overnight and Bob Costas. I read in a Playboy article that Letterman said he started in radio, so I thought that was a good idea. But the real reason that I didn’t go to art school is because when my father says they were “looking into it,” that means they never in any way looked into it.

Photo of a young Jimmy

Father Bill

Jimmy's childhood priest in Las Vegas

I’ve known him since he was 9 years old. He was always pulling practical jokes, none of them mean-spirited. It was a big thing back then in Vegas to cruise Fremont Street. He said, “Let’s go tonight,” and I said, “Sure, sounds like fun.” He and his friends got a fire extinguisher from the church in the car. We’re cruising down the strip, and I see them spraying it up and down the street. I said, “You guys gotta be kidding. I’m a priest, I can get in trouble for this” ... The flip side is he is a very generous person. His alma mater, Clark High School, had money from the school district to build a computer lab, but they ran out of money for computers. Someone in his school knew that Jimmy and I are good friends and said, “Do you think we can see if he’d make a donation?” He ended up buying all [72] computers.

JIMMY RESPONDS Father Bill was my first straight man. There is no better straight man than the pastor of your church. We became friends almost instantly. I was an altar boy and I started screwing with him almost immediately. We had this secret relationship—not like most secret relationships between priests and altar boys, but where he thought I was really funny and I liked him a lot too. We’d hang out with my friends. We had this priest that hung out with us all of the time.

Aunt Chippy

Jimmy's aunt and prank victim in real life—and on JKL

That guy has done more things to me than he’s done to anybody in his whole life. I mean, he did so many things to me that I’ll be honest with you—if I really wanted to remember all of them, I would never talk to him again. One time I open up a pack of cigarettes and he had written on every single cigarette: “You’re going to die today!” “This is your last day on earth!”... Then, at 10 years old, Jimmy started putting blow-ups in my cigarettes. It’s like a little white pellet. And you would put it in the tip of the cigarette. So as soon as you would put a match to it, it would blow. And all the tobacco would go flying…. I was at work and in those days you put your cigarettes on your desk. And people help themselves to your cigarettes. I get a call to go into the boss’ office. He says, “Close the door.” I’m like, “Uh-oh.” So I take a cigarette and put it in my mouth and light it and it blows all over the boss. And I was standing there going “Oh God there goes not only the job, but this guy is gonna beat me up.” I go around and I take all of the tobacco off of his clothes. It's all over the desk. Clean it up. And he looks at me and says, “Don’t ever come in here again after you’ve been to your sister’s house and your stupid nephew put blow-ups in your cigarettes.” And as I’m walking out of his office we hear another blow and one of the girls screaming. She had bummed the cigarette off of my desk and the same thing happened to her.... When Jimmy is gonna be within a 40-mile radius, I keep my cigarettes on my lap in my purse. I don’t let my purse out of my sight because he could get in there and do damage within four seconds. He is like a speed demon when it comes to that.

JIMMY RESPONDS A big part of my teenage years was finding new ways to get her cigarettes out of her purse and into my clutches and then to get them back into her purse without her knowing…. The great thing about her was even if one of the cigarettes would explode, she loved smoking so much that she wouldn’t throw the pack away. She’d still finish it. So if I loaded eight cigarettes, eight of them would explode on her. She’d be mad every single time and I’d get a call every single time. I wish I had those calls on tape because nothing makes me laugh harder than her yelling at me. I would like her to stop smoking but I also realize that’s part of who she is. She’s 40 percent cigarette.

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Breaking Into

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Kent Voss

Kent Voss

Jimmy’s first radio partner, with whom he hosted short-lived morning-drive shows in Seattle and Tampa

My wedding was in 1992. Jimmy was doing a morning show in Palm Springs. He’s certainly not flush with cash, but he flies from Palm Springs to Girard, Pennsylvania, so he can be in the wedding. We’re at the reception. I’m vaguely aware that there’s a mobile DJ there playing records, but Jimmy, who was a mobile DJ and did weddings, is noticing this guy is not doing a good-enough job. So he starts telling the guy, “You gotta play this song. You gotta play this song. I know these people.” And my wife’s like, “He isn’t doing a very good job,” so Jimmy’s like, “Screw it,” and he kinda pushes the guy out of the way politely, and he just took over. He was the DJ of our wedding—even though he was in the wedding party. It’s funny because some people might think, “Oh, he just wanted to be the center of attention,” and that is not true. He just said, “I want my friend’s wedding to go well, and he is not doing his job. I’m going to do it.”… He’s very loyal, very protective of his friends, and if he thinks whatever’s happening to his friends is wrong or an injustice, he feels the need to strike. He’s kinda like Sam Wainwright in It’s a Wonderful Life.

JIMMY RESPONDS It’s not the only time it’s happened. A bad DJ can really ruin a wedding. The reason I had to stop working as a mobile DJ is the pressure of knowing that it’s somebody’s wedding day and they’ve planned for it, especially the bride, their whole life. It’s a very important day-most people only get married two or three times. The pressure of making sure my equipment worked and that I did a good job was intense. I mean, rarely do I feel that kind of pressure doing this job. There’s much less pressure for me doing a television show.

Ben Stein

Ben Stein

Cohost of Win Ben Stein’s Money, Jimmy’s first TV job

Genius from the first f---ing minute that he walked in the door. He was the first person who auditioned. As soon as he finished, we said, “Well, we don’t need to see anyone else. He’s the guy.” I’ve been in Hollywood since 1976, and I’ve never met anyone smarter than Jimmy. No one. I’ve known studio heads and very powerful agents, but I’d say Jimmy is in a class by himself. We would often have on contestants who thought they were really smart or wise guys, and they would try to tangle with Jimmy in a battle of wits, and I would say to them, “Please, don’t even try.” And invariably, he would just cut them down to a little shred of themselves. I would never have wanted to go up against him. He is breathtakingly smart but also a man of the people. For someone to be that smart and also a man of the people is very, very unusual. Jimmy could be Secretary of State, Jimmy could be Attorney General, Jimmy could be a Supreme Court justice, and he would be better than any of the ones we’ve had for a very long time. Jimmy is the only comedian who could be President. If he were President, I would trust him to do the right thing, even though he’s a Democrat.

JIMMY RESPONDS Secretary of State seems like a problem. I’m sure I would offend someone immediately. I’d be a very bad Attorney General. I’d be a very bad Supreme Court Justice. I’d still be very bad at being the President, but of those jobs that would be the one that would probably be best for me…. I do remember one time there was a big, fat guy [on the show], and I made fun of him and I felt terrible about it afterward. I was so embarrassed. I would be lying if I said I didn’t regret some things—I’ve been caustic in situations that I wish I hadn’t been. I’ll think about them for the whole rest of my life. As I’ve gotten older I’ve learned to let things go and not everything needs to be a ‘Who wins this little battle?’

Adam Carolla

Adam Carolla

Former cohost of The Man Show and JKL writer

When I met Jimmy, he was driving an ’81 RX-7. The problem was, I didn’t meet him in ’83—I met him in ’94. I wanted to get into radio, but when I saw him pull up in that piece of s---, I was like, “Oh, I’m not so sure I want in anymore.” Everyone who knows Jimmy knows he’s not mechanically inclined whatsoever. The car had a million miles on it, and his clutch went out. Me, being this sort of blue-collar guy, I said, “I don’t know if it’s the clutch or the slave cylinder.”... I showed up to his house one day, and he said he pulled out the slave cylinder, rebuilt it himself, put it back in the car, and it works fine. I was dumbfounded. It was like coming home, seeing your dog eating a sandwich, and then you find out it made the sandwich itself. I was really impressed, because he’s an artist: He could draw, he could make things out of clay, he could do jokes and bits and voices. For that afternoon, he was Joe Six Pack: He got underneath his car, and he rebuilt the slave cylinder. It was a flash of blue-collar greatness, but it was lightning in a bottle, because he’s never achieved it again.

JIMMY RESPONDS It was the master cylinder.… I wouldn’t even have known to be impressed with myself for doing that if Adam had not pointed it out. I just bought the Chilton repair manual because I didn’t want to pay to have it fixed. On the other side of the coin, when I lived in Seattle, I tried to build a circular curtain rod out of PVC pipe. It took me like 39 trips to the hardware store and cost twice as much as it would have if I just bought it myself.

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Sarah Silverman

Sarah Silverman

Current friend and former girlfriend with 24 JKL appearances

In 2006 Jimmy and I took his kids to Seattle. [Kimmel has two children from his first marriage and a daughter with wife Molly McNearney.] I remember it was 2006 because Time magazine’s Person of the Year was “You” and the periodical had a mirror on its cover. The idea was we would fly to Seattle and drive to some incredible mountain Jimmy knew of with a “really cool view.” This was a lie. We were secretly driving to Vancouver, a city that his daughter Katie knew only as the place where her favorite show, Smallville, was shot. But that’s another story for another Jimmy Kimmel cover story. (In short, her mind was blown as we took a tour of the set and met the stars.) My story is a small moment at the Hudson News store in the airport. We were all scattered about among the candy, “I Heart Los Angeles” T-shirts, and neck pillows when Jimmy screamed for us from deep within the magazine section. “Sarah! Kids! Come quick!! OH MY GOD!! Hurryyyyy!!” And there he was, with the Time magazine held firmly adjacent to his crotch. “My balls are Time magazine’s Person of the Year!” And that, my friends, is one James Christian Kimmel. In a nutshell.

JIMMY RESPONDS I have to be honest and say there’s nothing I laugh at harder than my own jokes. I was pretty pleased with myself. I think I may have shared it with the cashier at the store as well. Thank God I have kids who appreciate that kind of thing.

Cousin Sal

Cousin Sal

Cousin, JKL writer, and on-camera prank master

He’s the most generous guy you’ll ever meet—our whole family is out here thriving because of him. Aunt Chippy is on the show, Uncle Frank was on, Cousin Micki is in the talent department, and he brought me on because of my prank prowess. But it’s really Jimmy who’s the best prankster. When his sister got married, I flew out to Arizona. We’re getting ready for the wedding, and [his son] Kevin, who was 3 years old, makes a bowel movement that’s inexplicable. It’s just all over the place, and Jimmy was in charge of cleaning this thing. Not only was I of no help, I was sitting in the background, pointing and laughing. As late as we were going to be to the wedding, it didn’t matter, because this was a great moment to see him struggle like this. We barely get to the wedding on time and I leave a couple days later. There was a weird smell following me in the airport in New York, and I check my bag when I get home. He’d put the diaper right in my luggage. I had traveled with that thing 3,000 miles. I had a message waiting for me on the answering machine when I got home: “How funny is it now?”

JIMMY RESPONDS I also tricked him into letting me give him a haircut. My radio partner, Kent Voss, said in front of Sal, “Do you have time to give me a haircut today?” I said, “Sal and I are going to the beach. We don’t have time.” I knew Sal would bite on it and he said, “You cut hair?” I said, “I cut Kent’s hair.” He’s like, “It looks pretty good.” I said, “Yeah, I’m pretty good at it.” He’s like, “Will you cut my hair?” I refused to cut his hair for six days in a row until his very last day—I have it on videotape actually—then I sat him down about an hour before I took him to the airport and I chopped his hair just to shreds.

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Jim and Joan Kimmel

Jim and Joan Kimmel

Jimmy’s parents

Jim We moved from Brooklyn to Vegas when Jimmy was nine and we would make trips to California. In those days, we typically went to Laguna Beach in some kind of cheap hotel or we’d go to San Diego and go to Motel 6, but we used to walk on the beach a lot with the kids, and on a number of occasions we mentioned, “Wouldn’t it be wonderful if one day we could ever afford to live down by the beach?” [In 2006], we’re in Hermosa Beach. We’re supposed to go for dinner with the family but he tells us that we’re going to go over to some park first and my great-nephew is going to play t-ball, which didn’t dawn on us—it was six o’clock, the kid’s two years old, you don’t play t-ball at that time—but we fell for it. My nephew Sal was there with his family and he said, “Aw, it got called off, the weather was windy.” Jimmy said, “What are we going to do? We’ve got a couple of hours to kill before dinner at eight o’clock.” So, he turned around and there were these townhouses and an open house sign. He said, “Why don’t we go in here?” Again, it didn’t dawn on us—you usually don’t have an open house at that time, but we went in anyway and we walked through the house. While we’re upstairs, we happened to look at the fireplace and over the fireplace was a picture of Joan and I in Italy. We looked at each other and he looked at us and then we started crying, he started crying. I said, “What, what is this?” He told us the story—that he always remembered when he was a kid walking by the beach [with us]. And that if there was ever one day he could get us something, he would. And he said, “This is yours.” He never forgot all those years.

Joan I think he got us the house because I was being a bad houseguest. I kept putting his dishes in the wrong cupboard when I would clean up, and it drove him nuts. That’s why he got us the house. But Jimmy’s story is nicer.

JIMMY RESPONDS They were driving me crazy. Their idea of coming for the weekend is noon Thursday to noon Monday. My maid quit in protest of my mother criticizing her work. There was just a lot of commotion in the house after a long week. But I was always planning to buy them a house. Even though it was a nice thing, I set it up like a prank. You could say this about almost anything in my life is: Good intentions and a good deed somehow gets overcome by annoyance… We go up the stairs and I’m very excited. I’ve been waiting for this. I’m covertly videotaping. It takes them forever to notice the photograph. There’s not a stitch of furniture in this house. The only thing on the wall is a big photograph of them. We’re up there for five minutes. Six minutes. Seven minutes. They’re looking around at everything and they don’t see the picture of themselves on the wall. I’m going berserk. Now it turned into an episode of Curb Your Enthusiasm where I finally go, “Is there anything that jumps out at you? Maybe there’s anything on the wall over here by the fireplace?” Then my rage turned to tears and it was a very sweet moment. I would say that there’s no better feeling than being able to buy your dad a car and your mom a house. That’s the best money I’ve ever spent.

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Ben Affleck with Kimmel
Ben Affleck

Ben Affleck

7 JKL appearances including his costarring role in
 “I’m F---ing
 Ben Affleck”

We have the kind of friendship that is actually rare in show business, where we did normal things, like I would always go over to his house to watch Lost. And when Lost was over, we’d watch Game of Thrones together. It’s just the kind of thing you’d look forward to and then bulls--- about the episode afterward, talked about whether you liked it or not. There’s definitely a lot of editorializing during the show, like “Don’t go into that room!” or now you’re nervous that the character is going to get killed off. Jimmy also gets the advance DVDs of Game of Thrones, so he’s a good guy to know. We go over there and then it’s like, “Let’s just watch one… All right, put in the second one,” then it’s 11 and you’re like “F--- it, put in the third one,” and then it’s 2 a.m. and you’ve watched four episodes of Game of Thrones, you become completely medieval..... That’s what I think is Jimmy’s appeal: his normalcy and his kindness, despite the fact that he can have some edgier material and he’s good at being an entertainer. He’s a good man. And it’s why I’ve been wanting to do the “I’m F---ing Ben Affleck” and all these bits. Because I trust him… He’s been kind enough to spare me [from his pranks]. Maybe he thinks I won’t come back and do any more sketches about having sex with him.

JIMMY RESPONDS Ben and I had not met when we shot “I’m F---ing Ben Affleck.” We did actually fall in love on that set. It was an all-day shoot, and then he came over to my house for several hours after the shoot and we just hung out.... We are right on the same page as far as taste in TV shows goes. He’s very, very bright. I recommend him as a television-watching companion. He doesn’t eat much, though.

John Krasinski


9 JKL appearances

We were in Mexico and no one wanted to go paddleboarding with me. Jimmy comes out and he’s like, “I’ll go with you.” So we go paddleboarding in front of the house. We were staying with Jennifer Aniston, and we were swarmed by paparazzi boats. They realized that if they revved their engine, it would create a wave, so they took turns trying to knock us off our boards for a better picture. They succeeded perfectly, because neither of us paddleboarded before. I was pretty bummed out that I couldn’t get a fair shot at paddleboarding because of these jerks. We get back into the house, and I tell the story, and Jimmy goes, “Did that happen?” I said, “Yeah!” and he goes, “I don’t remember any of that, because I am terrified of the ocean.” The dude who’s terrified of the ocean went paddleboarding just to make me feel good and then blacked out from fear—which is a perfect summary of what he’s willing to do for his friends. We went back to Mexico this year, and I showed him the pictures from the year before, and he still, to this day, does not remember that that even happened.

Krasinski and Kimmel paddleboarding

JIMMY RESPONDS I was so focused on not drowning that I didn’t see any of them. I mean, my head was under water a lot of the time. I genuinely did not know what he was talking about when we went back to the house and he told me that we’d been circled. He was like, ‘What’s wrong with you?’

Will Arnett


17 JKL appearances

I’ve had four or five half-baked ideas for business ventures and he loves the idea of ridiculing me about it. I can tell that he can’t wait for five years from now so he can say, ‘Remember you were going to do that stupid thing?’ I had this idea to do a vape cigarette, but instead of delivering nicotine, it delivered vitamin B12 or vitamin C—which I still maintain is a good idea. And Jimmy was like, ‘Oh, you’re going into the vape cigarette business? You’re going to manufacture them?’ and I’m like, ‘Yep!’ If we’re in a social situation, Jimmy will encourage me to talk about it, because it makes him laugh to hear me describe what I plan on doing. This is a testament to Jimmy—I know that he’s f---ing with me, but I’m still compelled to do it. He’s still able to get me to engage in a way that my feelings aren’t hurt. By the way, again, it’s a terrific idea.

JIMMY RESPONDS I know that if somebody told Will that they were going to basically create a Flintstones vitamin in cigarette form that he would find it endlessly funny. But since he’s the one that came up with it, he was seeing dollar bill signs in his head… I also have ideas that I think are great ideas that are not great ideas. I was fired my first radio job and was living with my parents. I decided that I would shrink down the covers of the National Enquirer and the Weekly World News to the size of a postage stamp using a Xerox machine. Then I made earrings out of them. I decided that women would like these. Of course, no women liked them. But I made hundreds of them, which I would then go around to stores in the Phoenix area trying to sell. I look back and it makes me evaluate ideas that I have now in a much harsher way. I know that I’m going to be making fun of myself in 10 years for them.

Lena Dunham


5 JKL appearances

I was sick in bed on a sunny L.A. Saturday with what turned out to be appendicitis, waiting for surgery the following week. Jimmy and Molly had invited me to a barbecue at their house, but I just couldn’t get out of bed. I emailed them my solemn RSVP, and Jimmy immediately replied, “Well, who is getting you soup?” Since the answer was “no one,” he hopped in his car and brought me his homemade tomato soup and bread. (Jimmy is also what my boyfriend would call a “restaurant quality chef,” and he still talks about the time Jimmy sent me home with homemade mozzarella, baguette and salami.) I was napping, so Jimmy left the soup at the gate, but it turned out to be the wrong gate. I wanted the soup so badly that despite my pain, I walked up and down the street barefoot at every gate hoping to find the bag with the soup. I couldn’t and sadly emailed Jimmy about the mix-up, at which point he offered to bring me more. Human decency prevented me from accepting this offer, but that’s the kind of dude he is: busiest man on earth, father and husband and chef, bringing you double soup when you’re stuck in bed. I love him.

JIMMY RESPONDS I still can’t figure out what happened. It drives me crazy. I made a really good tomato soup. I know I delivered it to the right place. Someone must have stolen that soup. What kind of maniac would steal soup? I obsess over things like that. I probably have given three full hours of thought to what could have happened to that soup.

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Molly McNearney


Jimmy’s wife and JKL co–head writer

MOLLY (AS WIFE) When we started dating, I would go back and forth between my place and his. I have my stuff at my house, and I like my own space. One time, he was in the bathroom for a very long time, and I just figured something was going on internally. A few days later, he presented me with this big box that had two of everything that’s in my makeup and Dopp kit, because he saw that I was lugging stuff back and forth, and he wanted me to be comfortable in his home. He was in the bathroom for that hour and a half with my bag going through every single thing: every lotion, razor, deodorant, shampoo, makeup. First of all I thought, “Well you could have saved a lot of money, because half of that stuff I never use.” But I was so touched that he would go that far out of his way to make me feel at home in his house. I remember calling my mom in that moment, and I said, “This is the nicest thing anyone’s ever done for me.“ My sister said, “Hang up the phone now and go have sex with him.” He really is the greatest wife you could ask for.... At Christmastime, our house is literally the North Pole. It has hundreds and hundreds of gifts, because everyone in our life gets a gift, and their child gets a gift. He doesn’t have an assistant buy gifts for him. He doesn’t buy one universal gift that everybody gets. Every single person gets a gift—and it’s specific to them. Our Christmas cards and stationery are all handmade by him; our wedding invitation, he drew. He makes vinegar, he makes pasta from scratch. He really is Martha Stewart. I’ve never met a man that’s so feminine and so masculine at the same time.

Kimmel and Molly McNearney at their wedding

JIMMY RESPONDS Hospitality is very important to me. When we have guests at the house—and I don’t even know if my wife knows that I do this stuff—but I’ll make sure there’s a pitcher of water by the bed and there are toothbrushes in case people didn’t bring them. There’s always shaving cream and a sewing kit. I want to make sure that guests don’t have to ask for things.... I am a very shy person by nature. I am always hesitant to ask for anything. I failed a test in college because I didn’t have a pencil and I was too embarrassed to ask somebody for one, so I took a zero.

MOLLY (AS CO-WORKER) Jimmy is relentless in his attention to every specific detail. The best example is the prank video we did with the wolf walking down the hallway in the Olympic Village. We were seeing all the stories outside of Sochi on the poor living conditions for the athletes. Jimmy saw that as a great opportunity to mess with the media. He called the writers together on a Friday afternoon and said, “Let’s come up with a way to prank the media using the Olympics.” We came up with the idea at 5 o’clock on a Friday and our producers jumped on it. This poor producer spent her Valentine’s Day going from hotel to hotel, sending us photos of interior shots, and none of them looked close enough for Jimmy’s liking: “The carpet doesn’t match the carpet in Sochi.” “The lighting fixtures are too old looking.” Nothing was good. “In order to pull this off, it has to be bulletproof for the trolls on the Internet who like to find those slipups and say, ‘That doesn’t match.’ ” We were looking through every photo online that any athlete had posted of the living situation, and we couldn’t match it exactly with anything here—so Jimmy insisted that we build a set. First, we had to find an athlete that was willing to do it, and a lot of athletes didn’t want to do it. Then we had to find the right athlete—we thought about Shaun White, but we didn’t think people would believe it from him, because he is a jokester. So we had to find someone that wasn’t known for their comedy. So we stumbled upon Kate Hansen—a luger. We contacted her and asked her if she would be willing to tweet the video. She was on board. So Jimmy asked her, “Can you please send us a photo of the hallway of your dorm?” Within 24 hours our set department had built an exact replica of the hallway of Hansen’s dorm in Sochi. The door handles matched, the font of the numbers on the doors. He insisted that the wolf used in that video was a species that would be found in Sochi. We shot on an iPhone probably nine times, because Jimmy was like, “You’re opening the door too soon or not soon enough—when the wolf looks up, you would close the door.” Did I mention that it was happening on Valentine’s Day?

JIMMY RESPONDS The human brain takes in a lot more than you might think when it comes to a comedy bit. If you can make everything as real as possible, people will be more surprised when the joke comes. [Once] I wrote up a 15-page document of how to shoot a fake press conference…. And it was Valentine’s Day, yeah. I think it was worth it. I don’t remember what we ate that night but I always remember tricking the world into thinking there was a wolf loose.

Apologies to Matt Damon—we ran out of space!