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Chatting with Chelsea Lately's Heather McDonald: Part 2

Heather McDonald's trip to her early days in LA traversing the singles scene
Heather McDonald's trip to her early days in LA traversing the singles scene
Photo thanks to Heather's MySpace page

At three years running strong, Chelsea Lately is at the forefront of late night talk shows, bringing daily news and pop culture tidbits into the spotlight in a dynamically funny and unique format, starring the brashly honest Chelsea Handler. From the very beginning, comedienne Heather McDonald has been a stalwart of the show, cracking up audiences with her spot-on impressions, witty quips as a regular on the panel, and featured spots on Handler's comedy tour. With a new book (You'll Never Blue Ball in this Town Again) and a national headlining comedy tour, McDonald's brand is one that stands on its own. She recently headlined at Denver's own Comedy Works, and took a break to chat with the Denver Comedy Examiner about everything from her beginnings as a stand-up and sketch comic in Los Angeles all the way to the rise of Chelsea Lately. This is part two of a two-part interview. You can read Part 1 of the interview here.

How did you get started in the industry? Was it improv, stand-up, acting?

I started stand-up first, it was the first thing I did right out of college. I didn’t study drama or theatre in college, I grew up in LA and at the time I was really jaded. I didn’t want to be a waitress at 27 -- not that there’s anything wrong with that -- but I very much wanted my own apartment, so my very first job out of college was this boring cubicle job. And then I got fired from that and I did actually end up working as a waitress, ironically. I was horrible at it. Then I started selling real estate, and that ended up being my normal job throughout my career. Which was funny because I’d be out doing a home inspection and someone would be like, “Uhh, were you on Drake & Josh last night?” and I’d be like, “Um, yes?” 

With comedy, I first did stand-up. I always loved sketch and improv so -- once I started stand-up -- I auditioned for a couple theatres. And one theatre was like, “OK, within 6 weeks, you can be doing your show on the stage,” and I was like, “Cool! I can find agents!” The other theatre was The Groundlings in which it took two years to get on stage. I was talking to my mom and I was like, “Don’t you think I should do the one where I can be on stage?” And she was like, “No, you go with the one that’s the best” At that time, The Groundlings were the crème de la crème of LA. It still is very good, there are just others that have popped up like UCB and Improv Olympics that just weren’t very popular back then.

So I was like, “OK, you’re right.” And it really is important in improv and sketch to be with the best people, because if you’re not working with strong improvisers the scene is going to die. It was like a graduate school for comedy. It was so much fun and really consuming. My whole life revolved around The Groundlings, which can be really unhealthy. I talk a lot about it in the book. Not a lot, but I talk about it because it was a really important part of my life. And I was doing both stand-up and improv at the time, and a lot of the sketch and improv people looked down on stand-up at the time because it was seen as like so hokey.

And my experience is that it’s the opposite now. I’ve heard some stand-up comics really bash the improv side of things.

You’re right, now it’s the opposite. Everyone realized that stand-up is such a better showcase because you don’t have to depend on other people. You don’t need a theatre. It’s just you, which makes it hard, but it’s a great, great showcase when you only have to depend on yourself. Sketch is still a great thing that people should pursue and it will totally help your act, but it’s important to have something where it’s only you.

So what format were you working in with The Groundlings?

It’s a program. You go through four levels and you have to pass each one until you get into the Sunday show. And once you get into the Sunday show, you have a guaranteed six months that you’re on stage every Sunday. Then they judge you again. All the main company members would vote on who they wanted in the troupe. Second City doesn’t do it that way, they have a group of people that are like the elders of the group, which I think is a healthier way to do it. Because sometimes there will be a person in the main company who might feel a little insecure and would say to someone else, “Oh, that person reminds me of so-and-so in the group,” and then they wouldn’t want them. So in my opinion it’s not really the healthy way to go because the insecurities of the current people can dictate who gets in. I don’t know if it’s changed, but that’s how it was.

I didn’t make it into the company; there were eight of us that auditioned for one spot because someone was leaving. There can only be thirty people at a time in the group, and none of us actually made it. It totally worked out for the best because I think I would have gotten stuck in there and more into pursuing, “Do I have a good show for 100 people?” rather than trying to find a job in writing. Which I did after I didn’t get the spot in the group, so it worked out.

What was your first big break into the industry?

Well, I did this show with MTV called “The Lyricist’s Lounge” which was a sketch show that was on for two seasons. That was really good for me, and I got a development deal with CBS. That didn’t go anywhere and my mistake was -- once I got on television -- I thought, “Good, now I can stop doing stand-up.” I got kind of lazy, so that was a big regret. That point is really when you need to up it. When this opportunity came around with Chelsea and people were starting to recognize me, I really decided to push it into high gear. I set a deadline for myself to have my proposal ready for the book. That was the main thing: What can I do while this is popular? I mean, there was a time when Arsenio Hall was the hottest thing in town. Not that we’re going to go by the wayside, but you just have to take advantage of the opportunities as they come. The book has been great and I really went for the stand-up again.

I did take a huge break from stand-up and it was kind of unconsciously. August 18th four years ago will be the first time I went on stage after a seven- to eight-year break. I didn’t realize until the girl I had done Pretty Funny Women with called me up and was like, “You know, I really wish you hadn’t quit stand-up, you were so funny!” and I didn’t even realize that I’d stopped doing it. She gave me a date about a month away, and I was forced to write an entirely new set because all of my old jokes were about dating and being single. It really forced me to keep going. And I really love stand-up. It’s one of those great things that you can always do and I never want to let that much time go by again without doing it.

So do you see stand-up as a foundation for the comedy industry?

I mean I think it’s really smart to keep it up. If you do get to the point where you’re known and people start coming to your shows, you can start doing the bigger theatres and your audience knows what to expect from you. At that point, stand-up isn’t as much of a hurdle anymore, as exhausting as it is. As long as people continue to come to your show, you should continue to do it, ya know? As long as it’s still fun for you, you should do it. And there are those bad nights, but stand-up is kind of like going to the gym. It can be horrible and self-revealing, but you feel the best after you do it.

In writing the book, is that something you had always wanted to do?

Yes, definitely. I had always kept notebooks about dating and that whole period of my life. A lot of people had asked me, “Oh you know, is this about being married and being a mom?” and I just wasn’t ready to write that kind of book. I really wanted to highlight this particular period in my life for my first book.

And you’re at four weeks on the best-seller list?

It’s definitely going really well. What I didn’t realize was how hard it was going to be to constantly promote the book. Each book counts so much, and that is a really tough part of the process. But it’s been really rewarding to have people read the book and email me back saying that they’re addicted to cracking their back too or all these little funny things that I was laughing as I was typing it. To know other people are laughing reading it is really, really cool. It was fun doing the narrative in that particular way, and it felt really natural to me.

So has writing been the ultimate goal for you?

No, the ultimate goal is to be on TV more often. And whether that’s a sitcom, I’ve always wanted to star in my own sitcom. Whether it’s single-camera or traditional. I also love the format of giving my opinion on things, whether it’s like a panel View-type sort of thing or whatever. I’m just really excited to see where things go because there’s a lot that I can do, so I’m just really open to whatever opportunities come along.

Thanks so much for reading Part 2 of the Denver Comedy Examiner's interview with Heather McDonald! Feel free to shoot Nicole an email about anything comedy-related and def remember to follow her on twitter at DenverComedy!

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