Long Island native Wendy Liebman graduated from Wellesley College with a degree in Psychology in 1983 and began her stand-up comedy career in 1985. She has since performed on late night talk shows hosted by Johnny Carson, David Letterman, Jimmy Fallon, Jay Leno, Jimmy Kimmel and Craig Ferguson. Liebman turned 50 the same night James Franco and Anne Hathaway hosted the Oscars, and two weeks later, before family and friends, took the stage for what became her first hour-long Showtime special, Taller on TV. Liebman is married to writer/producer Jeffrey Sherman, and together with two stepsons and one rescue dog they live in Studio City, California. She has listened to Joni Mitchell’s Court and Spark more than any other album over the course of her lifetime.

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My life, in reflecting on this question, it’s all sort of a big blur. Maybe I need better glasses.

I have embraced turning 50 like nothing else in my life that I’ve ever done [laughs]. I decided about two years ago that I was going to make a huge deal out of turning 50, and I decided to record my first DVD on my 50th birthday.

I’ve been doing stand-up comedy for 27 years and I’ve never recorded or taped a DVD or a CD. I’ve managed, somehow, to never do that. I mean, there are tapes of me on the Internet, but nothing that I produced and generated by myself, so I decided to invite everybody I knew to celebrate with me and be part of the taping. It’s the first time I’ve ever invited the audience. I’ve invited 300 people and I’ve rented a theater.

I couldn’t actually get the theater on my 50th birthday because it was already booked, so I’m doing it two weeks after. And at first I told everybody. Like about nine months ago, I wanted to make sure that people saved the date and I told people that I was celebrating my 50th by taping my first DVD. But then as it got closer and the more people I invited, I just made it about the taping. I didn’t include that it was partly to celebrate my 50th.

The DVD is going to be called Playmate of the Year, because I was voted that in kindergarten. And it’s my stand-up, which can be a laugh every ten seconds, but I’ve also included another section, or a couple of sections, where I get kind of philosophical and reflective. And the last thing I say is “Happy birthday,” so it’s a celebration of being alive because so many friends, peers and classmates are turning 50 right now, too. So yeah, I’m making a big fucking deal out of this [laughs].

My husband made a big deal about my 40th. Actually, we weren’t married yet, but he threw a big party for me on my 40th. But that wasn’t my baby. This is the first time I’ve ever made a big deal out of my birthday.

I remember thinking about friends who threw themselves 30th birthday parties, 35th birthday parties, and I thought, not that it was egotistical, but that it was almost sad that they had to throw it for themselves. But I feel like I want to celebrate. I love the people in my life. And what’s even more exciting for me in thinking about this upcoming show is that they all get to be with each other. That’s one of the joys of my life, is that my friends become friends with each other. And like just this morning I’m going over the guest list and seating everybody because I want them to sit near people that they might have something in common with that they wouldn’t have met before.

It’s my fantasy in life to have everybody in life all the time wear a nametag [laughs], “Hello, my name is…” because I like that kind of familiarity. And I think people are nicer to each other when they know your name.

I never have trouble with my birthday, because I feel so immature. Well, I’m immature according to my pediatrician.

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My mother was going to have another child, but I was colicky, and so my crying sort of prevented me from being the middle child [laughs].

I wanted to be a go-go dancer. I really, really, really wanted to be a go-go dancer in the white vinyl boots and the big earrings, in a cage, dancing. Or else I wanted to be a notary public [laughs].

Well, first I wanted to be a go-go dancer and then I wanted to Julie Andrews. I really wanted to be Julie Andrews. And I remember telling my sister that my parents were going to be wasting money on orthodontia with me because I was going to just get my teeth knocked out and replace them with teeth that looked like Julie Andrews’s teeth. I really wanted to sing and I loved The Sound of Music. That was my favorite movie. I also loved Barbra Streisand in Funny Girl, and I grew up wanting to be Barbra Streisand, too.

My grandmother said that go-go dancers came from bad families. And I thought, Perfect. But stand-up comedy’s okay, I guess.

I had a midlife crisis when I was 16, so I thought I was going to die at 32.

By the time I got to college, I’d always been in the plays. I was Eliza Doolittle in My Fair Lady. I was Dorothy in Wizard of Oz. But I became very serious and philosophical and chain smoky, and I was going to be a psychologist. Not a psychiatrist. I didn’t want to go to medical school.

I didn’t have a sense of humor. And actually I’ve just been connecting with my prom date on Twitter who said I wasn’t very funny in high school. And I think that’s true. I wasn’t funny in high school. My best friend was. But I went to college really to be studious. And it wasn’t until a few years after college that I found… I don’t know if it’s that I’m an exhibitionist. Not even an exhibitionist, just an extrovert. I’m an introverted extrovert who needs attention, but deflects it off of myself by making people laugh.

Somebody asked me why my style was the way that it is, which is I make you laugh and then you think you’re done laughing and then I make you laugh again, or I try, and it’s because I really don’t like being onstage with silence, because then you actually look at me or focus on me. And I don’t want that. So I’m twisted.

I went to college really thinking I was going to become a quote unquote professional psychologist. And I worked in psych research for a year after college, and I just thought, I’d rather make 200 people laugh and be happy for an hour than just one person. I just thought I’d be better 1 on 200 [laughs].

I took the mail in from the wrong apartment once when I was living in Brighton, Massachusetts, and there was a course catalog for the Cambridge Center for Adult Education, and I thought, Oh, I should take a class, because I was doing psych research during the day and I found it really depressing. So I took a class in acting, because I’d always been acting. And I went to the first class and then the teacher quit. It had nothing do with me, that he quit. And then they said, “Well, you can take another class.” And I’m like, What else should I take? And there was a class on how to be a stand-up comedian. And it was the angels opening up the heavens [laughs]. I just read that and I thought, That is me. And I guess I’d been to a comedy club before that and I watched some comedians. And not that I thought I could do better, but just like I identified with them up there. I could totally see myself doing that. And it was also after that I had to work my ass off. I mean, really work my ass off. But it was, I don’t want to say fate but—does that sound corny?—to become a stand-up comedian, it just was exactly what I should be doing. Now I’m not so sure [laughs].

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I actually think that stand-up comedy is one field where you really do get better as you get older. I have, for sure. It’s one of the things that keeps me doing it still, is that I think it would be a shame if I stopped because I am getting better at it 27 years later. But I’m a slow learner. It took me a long time just to feel comfortable onstage. Longer than most.

I’ve thought of retiring from doing stand-up many, many, many, many, many times. And it’s almost like I went through the tunnel, and now I’m at the other end where I feel like I’m so much better that my job becomes easier. But I would like to do other things. So I don’t know if I would ever retire. I might retire from going on the road, doing stand-up, but I think I will always be a performer.

There’s a restaurant right around the corner, within walking distance, that has started doing stand-up, and I actually said the other day, “I should just go there and host the show, and then I’ll never have to leave my dogs, my family.”

I love to sing. And I’m not a professional singer, but I have sung onstage in my act occasionally. And I sang once in college. I was in the play Hair. There was no nudity, but I sang a song called “Frank Mills” and it was another moment of such joy in my life, because I feel like that is a way for me to touch people when there are no bells and whistles. I don’t have a voice like the pop stars but I have—let’s see, how do I explain this?

The other night after a show in Washington, DC I was done with all of my shows and I had been performing for a month, and I went back to the hotel with a friend and we were going to grab a bite in the lounge in the hotel, and there was a karaoke set-up. And there were eight people in the lounge, and they were passing out slips of paper and I signed up to sing, but I used an alias. Not like anybody knew who I was, but I just felt like if I wasn’t me it would be easier.

So I went under the assumed name of Libby [laughs]. And it was the night before Valentine’s Day and I did a shout-out to my husband back in Los Angeles. I sang “I’ll Be There” by the Jackson Five, or whoever wrote that. So there was like 15 minutes of waiting. I was so nervous, in a way that I used to get nervous before I did stand-up, but I haven’t felt that in years. I was so nervous, but excited. I wanted to do it. And by the end of the song I had like all eight or ten people waving their hands back and forth, holding up candles and lighters. I had the bellhop guy come in to see what all the commotion was about. And it was joyous for me to sing in public. I’m too old to make a career out of it, but it’s something I would like to do more.

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Okay, so I’ve already gone through menopause. Three years ago. What a waste. I never had kids. My breasts have grown a size, more than a size, and I’ve had to buy all new bras.

My voice has gotten deeper, like Joni Mitchell’s [laughs]. I mean, I don’t smoke anymore and I haven’t smoked in years. The hardest thing in the world to do is to quit smoking, and if I have any kind of platform at all in my act it’s to tell people that, that they should never start. Because I was sort of given a second lease on life just recently.

It’s been hard for me to breathe. And I thought maybe all those years of smoking had caught up to me, because I smoked a lot. And I guess part of it is hypochondriasis. And I am a Jew from Long Island so I always go to the crisis, that I’m going to have a hole cut in my throat because I can’t breathe anymore. And finally I went to a doctor and he stuck a camera down my throat and he said there’s no damage. But I have allergies. So all this time I’ve thought, Oh my God, I’ve fucked up my lungs, the one thing that… Even the liver grows back. You can get a kidney replaced. Your lungs? Forget it. And I hugged the doctor. I’m like, “I don’t care if I’m allergic to my husband or my dog [laughs].” Yeah, so I do feel like just this week like my health is really good.

I’ve lost a lot of comedian friends, and arguably all too young, and a lot recently. And not only friends but just other comedians, people in my profession. Casualties of drugs or illness. And I think when people die that energy is then dispersed into the people who are still alive. I think that whenever a comedian dies, I feel that much funnier or invigorated or inspired to be my truest self, which is funny, innately.

My husband’s analogy is that we’re next on the conveyor belt. Like when our parents die our mortality’s closer. And I think in a way that’s one of the reasons I am so embracing being 50. Not that I’ve been tentative in my life, because God knows you have to be sort of bold or courageous to get on stage in front of people and pretend you’re the leader.

I used to be so scared of public speaking. Like I had such social anxiety that I remember when I was 10 I was on a plane and I saw the flight attendant take the intercom, and she was behind the galley. She wasn’t even in front of people, but she was talking over the intercom and my heart was pounding for her. And I would watch the Tonight Show and feel so nervous for those comedians until they got their first laugh. Like I so identified with that. So getting to 50, or getting older, not just to 50, I guess part of why I feel better at my job now is because I feel like I have earned the right to be there. I’ve paid my dues, and so that part of the equation is a little bit diminished. I don’t have to prove, as I used to, every time I got onstage, that I am rightfully there.

I performed in Boston once and Bud Friedman, who owns the chain of Improvs, was in the audience. Actually it was his wife who elbowed him and said, “She’s funny.” And that sort of was the turning point in my career, in my life. I moved out to L.A., and from that I got on the Tonight Show with Johnny Carson. And not that any one thing changed that dramatically other than the shift in my mind, but it was when Alix Friedman told Bud Friedman that I was funny that my life changed.

When I smoked it reminded me to breathe. I mean, I joke a lot that I was addicted to the second hand smoke in the comedy clubs, because you can smoke in there, and like even to this day I love the smell of smoke even though I won’t smoke anymore. But I also am addicted to laughing, because laughing also makes me breathe. I know that sounds so silly but, you know, they have done all these studies about how laughter helps to raise endorphins and the best medicine, yadda yadda. It really is about aerating yourself. And I guess I could exercise more, but I prefer to laugh.