Jimmy: They’re not healthy, but they are definitely—
Judd: You liked them?
Jimmy: They were great. I had a great childhood.
Judd: Are your parents still around?
Jimmy: Yeah, I talk to them almost every day. They are great. They belong in a mental institution, but besides that, very nice people.
Judd: (Laughs)
Jimmy: They were funny people. We were an Irish Catholic family, so we’d have parties. My dad loved to listen to music, so we always had the radio on, and so they would have parties and people came over and after a couple of hours people would stand up in front of everybody and sing a song. And then everyone clapped and then someone else would go, “No, you sing one,” and then someone would sing “I Left My Heart in San Francisco,” and then someone would sing “When Irish Eyes Are Smiling,” and then my grandfather would get up and sing last, some song, and everyone would start crying because it was a really sad Irish song. And that was the end of the night. But we’d all have a good laugh, my grandmother did bits—my grandparents lived right next to me, almost in my backyard, in a little guest house almost. They kind of helped raise me. I really got a lot of my sense of humor from watching them do bits, but we would listen to comedians on Sunday mornings. They would play this channel, an AM radio station that would play comedians, and we would listen and—it was fantastic. We used to listen to the radio and just laugh, and go, “Oh my gosh.” And then I started getting into it. I really loved comedians, so my dad would buy an album like Rodney Dangerfield, No Respect, and he would—I remember this—he would take a key and scratch out any of the dirty words, so that when I played the record, it would skip over the curse word.
Judd: That is hilarious. And you were never a dirty comedian.
Jimmy: I never was a dirty—no, I never was.
Judd: But your show now, in a way, is like sitting around, singing songs at the piano, enjoying people. Is that how you see it? I mean, the idea of my crazy Jewish family sitting around, singing a song, is unfathomable.
Jimmy: This was a weekly event. This would happen all the time, and everyone would get involved. My sister wasn’t as into performing as I was, but we would play “King Tut” and come downstairs in my mom’s dresses—the ones that looked kind of Egyptian—and we would dance and lip-sync “King Tut.”
Judd: See, I did all that and no one cared and I was alone.
Jimmy: (Laughs)
Judd: It’s like we have the same story—if everyone ignored you and you just watched Love Connection alone in your room every day for seven years.
Jimmy: I look back, I mean there are tapes of me doing Pee-wee Herman and impressions of people, Michael Jackson, Eddie Murphy—
Judd: I remember meeting you when you first got to SNL, I remember seeing you there. And I remember you did an impression of Adam Sandler.
Jimmy: That was my breakout episode. Ben Stiller was hosting.
Judd: That’s right. It was the Stiller episode. That’s why I was there.
Jimmy: It was a Halloween episode, Ben Stiller hosted, and I remember Ben said to Higgins, “Hey, this kid does a great Sandler.” They go, “Yeah, yeah, we’ve seen it, but Adam doesn’t have a movie coming out, so we’ll wait until something—” and Ben goes, “No, it doesn’t matter. You should have him do it.” So we wrote up celebrity Jeopardy, where I did Sandler and Ben did Tom Cruise and Daryl did Sean Connery. That same episode is when I played guitar and did guitar impressions with Colin Quinn on “Weekend Update.”
Judd: Yeah. Wow.
Jimmy: Usually, if they know that a bit is going to kill, they’ll put it at the end of “Update,” but they didn’t think I was going to work that well, so they put me in the middle—and I crushed. It was a good bit. I did impressions of Alanis Morissette and all this stuff and no one knew—I was brand-new. It was my third episode, I think.
Judd: That’s the biggest moment, when you realize you’ve found something that will make you break out a little bit.
Jimmy: And that was it. I was the impressions guy. It all started happening from that one episode.
Judd: You try so hard to figure out what will make people notice you—
Jimmy: I remember I called Adam before I did it, because I wanted to make sure I had his blessing. They called him and put him on the phone with me, and I was so nervous. I was like, “Hi, Adam.” He goes, “How ya doing, man? Let’s hear it.” I go, “Okay.” I go (making funny sounds), I go, “All right, I talked to my mother the other day and she said, “What is wrong with you? There’s something wrong with you….’ ” And I was doing this whole bit, and he goes, “All right, that’s good. That’s good. You gotta do it.” He was awesome.
Judd: That’s because no one ever calls or shows any respect in that situation. I remember Dana Carvey did Shandling on Saturday Night Live. It was really mean, and not a great sketch—I think Carvey called Shandling up after and was like, “Oh, I’m so sorry,” and Shandling wasn’t thrilled about it. Garry just said, “You know what? We’re going to do a Larry Sanders episode about it.” And then they wrote an incredible Larry Sanders where Larry was mad when Dana Carvey guest-hosted—he did an impression of him and tore him apart.
Jimmy: I remember that. It was a great one. Out of all the things I watched to get ready for this job, Larry Sanders was the ultimate—that’s the ultimate piece of advice I’d tell anyone to watch if you’re doing a talk show. It’s so real and so well done. That’s how a show gets made.
Judd: It seems like effortless, the way you generate all this material.
Jimmy: Well, I think you have to keep trying and keep swinging and get up to bat and try a different type of joke, because you don’t know which one is going to connect. We try a lot of stuff that doesn’t work, and you go, like, “Wow, that one did not work,” but we tried it. And that’s what you have to do. I remember—it was the first season of Late Night, and you were nice enough to come on the show and you go, “This is great, this is fun, but honestly, remember these years because you will not be doing this much pre-tapes and stuff down the road because you guys will burn out. There’s no way.” And I really took that to heart. Every time I’m like, “We don’t have time to do that,” I think, No, you know what, I’m going to make Judd Apatow proud and I’m going to stay late, I’m going to stay till two in the morning. I swear to God, I think about it all the time.
Judd: Because Letterman, there was a moment when he just stopped going to New Jersey and knocking on doors, doing bits.
Jimmy: But that was the best part.
Judd: It was. It was incredible. And I felt a deep sadness when I heard he was not going to do remote pieces anymore.
Jimmy: He was the best at it.
Judd: It must have been odd to go up against Letterman, since he’s the one that made us all want to be funny.
Jimmy: Yeah, but it’s just the way it worked out.
Judd: Do you ever interact with him?
Jimmy: I don’t. You know, we started joking back and forth a while ago. He would say—he would try to tweet me. Almost like he didn’t understand Twitter. He’s like, “I’ll tweet Jimmy Fallon!”
Judd: That’s funny.
Jimmy: It was a funny bit. Then, I would try to teach him how to tweet through Twitter, and then I think CBS asked him to stop.