Being funny isn’t easy. It’s difficult to make people laugh. When you are successful at the act, brilliant at the process, being funny comes with its own set of burdens. For starters, people always expect you to be “on” at all times. “Make me laugh! Dance, monkey… dance!” And of course, you’re only as funny as the last joke you told. Applause can quickly transition into heckling.
Luckily for Rachael O’Brien, a true multi-hyphenate in the entertainment industry, she has a natural ability at finding the funny in the everyday experiences and life moments that makes her relatable point of view work with comedy club audiences and podcast listeners alike.
We recently sat down with the “Be Here For A While” host to discuss late night brainstorming, the unexpected work that goes into managing a podcast, and why she needs to clean to write.
TrunkSpace: You are involved in so many different aspects of the entertainment business. If we trace things backwards from today to the source, what would we find in terms of the starting point that got you interested in the entertainment business?
O’Brien: Watching “Saturday Night Live.” I was obsessed with it as a kid, really obsessed with Chris Farley, David Spade, Will Ferrell, and Cheri Oteri. That sort of era. I used to reenact the Spartan Cheerleader skits with my dad at parties.
O’Brien: Yeah, it was awesome. Very cool.
But, yeah, it was probably watching SNL. I just thought, “That’s what I want to do!” and I figured I’d move to New York and be on SNL, which is strange because I ended up becoming a stand-up comic, which is way different than sketch comedy.
TrunkSpace: As you look at all of these different aspects of your career now, how do you manage them and give them all equal attention? It seems like it would be a lot to manage.
O’Brien: Yeah, it is. It’s certainly not easy to manage, but it’s manageable because I love it, so I’ll make it work no matter what, if that makes sense.
TrunkSpace: For a lot of creative people, particularly writers, they have a hard time shutting their brains off. Are you ever not working?
O’Brien: Never. Absolutely never. I mean, in the middle of the night, not last night but the night before, I woke up probably six different times. I don’t take notes. I send myself emails because it will be an alert when I look in the morning. I woke up six different times in the middle of the night to send myself emails like, “Write this into a script. This would be a good joke.”
TrunkSpace: So when those ideas come to you, do you know where they’ll exist, as in a script or as a part of your stand-up material, or do they evolve?
O’Brien: It sort of just evolves. And sometimes I never even use them. I just have the thought, and then I forget about it sometimes. It’s actually more work sometimes to go back and look at the notes I’ve written. I’m like, “Oh, that was a joke that would have been really good.” I forget about it.
TrunkSpace: It’s something musicians reflect on a lot. Coming up with a riff or guitar part and then, poof, it’s gone.
O’Brien: Yeah. Exactly. Maybe it’s because a lot of people overthink stuff when they’re sleeping, and then you just sort of forget about it.
TrunkSpace: You run a podcast called “Be Here For A While.” Other than giving you another creative outlet, what does having a podcast mean to your career? Is it an important part of the equation that comics need to tap into?
O’Brien: I don’t think you have to, but it’s really helpful because podcast fans and listeners are not like any other type of fan. They really feel like they know you, and I actually feel like I really know my listeners. So it’s like building a really strong listener fan base, because you’re talking about your life and it’s personal. It’s a once a week thing. I think it’s extremely important.
TrunkSpace: Does managing the podcast add an extra layer of stress because of the consistent frequency of it?
O’Brien: When I first started my podcast, I was like, “Oh, cool, it will just be this fun thing I record once a week. Whatever, I’ll have my friends on.” It’s a lot of work, because you’re, also, constantly doing other people’s podcasts because that helps build listenership, and once you get sponsors and ads, that’s a ton of work. And there’s your listeners. I give my email out to my listeners, and so they’re always emailing me and I want to respond. Sometimes I call them because I don’t want to respond in a long email. They’ll email me for dating advice and it will be a super long email and I’ll just be like, “I think it might be just easier if I call you.” (Laughter) I just tell them to give me their phone number and I call them.
TrunkSpace: From an outside perspective, it seems like the toughest aspect of running a podcast is coming up with a fresh point of view.
O’Brien: Yeah. I don’t really have a major concept. Mine’s just about comedy and life. I just talk to other comedians. I don’t know. I just have different guests on, and I interview people a lot. I had a psychic on this week. That was pretty cool.
TrunkSpace: Does the podcast lead to people coming out to your live performances and do the live performances lead to people listening to your podcast? Seems like it could help out on both sides.
O’Brien: Yeah, definitely. I get more people coming to my comedy shows through my podcast. My podcast listeners will come and I also do live podcasts in comedy clubs. Yeah, it definitely helps that.
TrunkSpace: Sticking with the stand-up side of things, is that world a bit more of a boy’s club than other areas of the business, particularly when it comes to the club owners and those who book the events?
O’Brien: It definitely can be. I try not to think about it too much because I’m not someone that’s like, “Oh, I’m at a disadvantage because I’m a girl,” or, “I’m at a disadvantage because of whatever.” There are definitely more white male comedians than anything else. Yeah, it is a boy’s club, but you can’t think of it that way. If you’re going to survive, you just can’t think of it like that. I just try not to get bitter about that kind of thing. It’s like, “Well, it is what it is.”
TrunkSpace: Are the people who exceeded their two drink minimums more apt to heckle a female comic?
O’Brien: No. I think when people get drunk, they just will do anything. Being a female comic can, also, come at an advantage because you’re a smaller group. “Oh, we need a female comic on the show.” You’re not competing with 3,000 people. It’s a smaller pool of people.
TrunkSpace: You’re also coming at things with a different point of view.
O’Brien: Exactly. It can also be an advantage.
TrunkSpace: When it comes to writing material for your stand-up, how often do you try to switch it up and add to things?
O’Brien: I try to all of the time. Sometimes it’s hard. It depends on the show though. It’s like, if I’m on a show with huge, all-star headliners at the Comedy Store on a main room show at 8 p.m., I’m probably not going to try out new material, because I want to do my best stuff. But if I’m doing a bar show, or if I’m in Reno, Nevada doing seven nights… that’s where I was on my last tour… and no one knows me and it’s 7:30 p.m., yeah, I’ll try out new material then.
You have to choose the show to do it on, but I try to do it as often as possible.
TrunkSpace: There was a time in the 90s when every stand-up comedian was getting his or her own television series. It feels like we’re venturing back to that area of things.
O’Brien: Yeah. That happens a lot. That’s half the reason why I got into comedy. I went to grad school for screenwriting and I liked to write comedy pilots. I was like, “How do these people get these made.” They were stand-ups.
I think that’s happening again. Yeah.
TrunkSpace: What’s the ideal headspace for you to be in to write?
O’Brien: I’m a mess when I write. There is no ideal headspace. It’s so hard for me to… once I start doing it, once I force myself to do it, I can do it for hours and hours, but I will clean my house three times over to procrastinate from writing. I will do anything to procrastinate it because it just freaks me out. So there is no ideal headspace. It makes me crazy.
TrunkSpace: Nothing wrong with that. We need a clean workspace to get stuff done.
O’Brien: Totally. I’m cleaning right now while we’re talking. Everything needs to be perfect before I can settle in to do something like that.
Listen to “Be Here For A While” here.
O’Brien also appears on Bravo’s “Vanderpump Rules.”