(CSC) 1. You’ve been pretty busy touring all over the world this past year! What’s that experience been like for you so far?

(Jennifer O’Brien)

Yes we have and coming up in February I will have been with Dolly for twenty years, off and on. It’s different but it’s always the same. (Laughs) That may not make sense but it is true. There are different groups of people, venues, and shows at every tour stop. It’s always wonderful because she’s (Dolly) there! The crowds overseas have been so enthusiastic and supportive of Dolly and her music… It’s unbelievable and electrifying.     

(CSC) 2. Working with Dolly for as many years as you have, how did that opportunity come together for you to work with her, and what do you enjoy most about it?

(Jennifer O’Brien)

Well I had just come off the road with George Jones and had decided that I wanted to do session work. So I got into session work and did really well with it. I started doing demo sessions for Dolly’s publishing company, my friend Stella; her sister, put all of that together. After one of the sessions Richard Dennison asked me if I had ever thought of going back out on the road, and I told him not really, but what did he have in mind? He told me that Dolly was getting ready to put a show together for the road, and he’d love it if I’d audition. So I auditioned, and got the job!  

(CSC) 3. When did you first realize that you wanted to become a part of the music business?

(Jennifer O’Brien)

I started singing when I was two years old. My parents told me that people would come over to the house and ask me to sing for them, but I was very shy and would walk under the table. They said I didn’t have to duck because I was so small; so I would sing for the people that way. (Laughs) My dad started taking me around to talent contests when I was two and three years old in my home state of Wisconsin….of course if you were under seven or in a wheel chair, you always won! (Laughs)

(CSC) 4. Growing up in Wisconsin, what was that like for you?

(Jennifer O’Brien)

It was cold, (Laughs) it was very cold. I started on a local radio show at eight years old called Amos Shepard and The WBEL Trailblazers and was known as Little Miss Ginny Lee. That was my first stage name. I couldn’t reach the microphone so I would have to stand on a chair to sing. That was my very first entrance into professional music; I earned two dollars per show.

(CSC) 5. Who were some artists in the country music business that inspired your style of singing?

(Jennifer O’Brien)

Growing up as a little bitty girl I loved Brenda Lee, Connie Francis, and Kitty Wells. I was a little older by the time Dolly came onto the scene. I can remember always loving different kinds of music. I grew up singing mostly Country Music as a young girl, and in my teenage years I was in a Rock & Roll band, but Country Music was always my favorite. Since moving to Nashville and being introduced to Gospel Music, it has now become the new favorite.

(CSC) 6. What is an average day like for you living life on the road, any ups and downs?

(Jennifer O’Brien)

Well it can be hectic depending on how far away the next venue is. A lot of times we’ll get done with the show, leave around eleven or twelve, and then travel for about four or five hours until arriving at the next destination. Once you get there, you have to get up, so your sleeping pattern is broken up. Sometimes it’s hard to get caught up on your sleep if you have a lot of one nighters, it’s always nice to be able to sleep in a hotel. I like pretty much everything about touring though! I love being out on the road, but also love going home. We’ve been very busy, and have been gone a lot, so it will be good to have a break. We’re all very sad though because it doesn’t look like we’ll be traveling next year (2009).     

(CSC) 7. Having the chance to work with several artists in your career, what are some important lessons you’ve learned from them, and how do you apply it to yourself?

(Jennifer O’Brien)

I’ve seen both sides, so I’d have to say that it is very important to stay grounded. The road is kind of a fantasy world; it’s hard because most people see you up on stage for that hour and a half to two hours, but there is so much more to it. I’m sure you know what it’s like because you’ve been around it enough to know what else goes on behind the scenes. I try to stay grounded in Jesus, through the word because that’s what keeps me centered.

(CSC) 8. I know that you often perform with Carol Lee Cooper at the Grand Ole Opry in Nashville, what’s that like, and what do you enjoy most about the Grand Ole Opry?

(Jennifer O’Brien)

I love Carol Lee! She calls me often to sub with her on the weekends. That’s one of the scarier things that I do because you rarely have rehearsal time. Sometimes when a song is being kicked off, I’ll look at Carol Lee and ask her, do I know this song? (Laughs) Here in town the Nashville Number System (a method of writing music charts) is used by most musicians. And then Carol Lee will give me my starting number and I’ll jump in head first!

(CSC) 9. What’s it like working with the legends of the Grand Ole Opry?

(Jennifer O’Brien)

There is nothing like the Grand Ole Opry! I’ve seen it change a lot over the last few years… they’ve got new management and sometimes I think they’re trying to make it like every other show; and its just not. It’s so unique and I really pray that they don’t lose that specialness. It’s so casual there; people can be out on stage, and there’ll be people walking around and socializing with each other. (Laughs) You’d think it wouldn’t work, but somehow it does, it just works!     

(CSC) 10. Did you ever have plans, or aspirations to become a solo artist in the business?

(Jennifer O’Brien)

That’s why I came to Nashville, but it just didn’t happen. I got a recording contract with Atlantic Records and the day after my record was released they closed the Nashville office. (Laughs) It just didn’t happen, and I really kind of thank God since then for not answering my prayers because I would’ve cut my right arm off to be an artist. Now I look and see what it takes, and I see how most of the times there’s not a lot of longevity. Of course we know that Dolly is beyond all that, but when you look around there are very few artists, especially more now than ever that if they have a five year span they are considered lucky or blessed. George Jones said something to me one time that I’ll never forget. I had been in town for about six years; and I come from a small town in Wisconsin. I worked in the hotspot club there in town and when I came to Nashville just knew I was just going to be the next biggest thing since sliced bread. (Laughs) So one of the few conversations that I had with him was about the first time I came to town. I told him when I first came to town I had no doubt that I was going to make it, but now was starting to wonder if things were going to happen. Then he said to me, “I’ll tell you something worse is to make it, and then lose it because you know what you’re missing.” I thought that was pretty profound.

(Country Stars Central)

It’s kind of like you have the best of both worlds. You have the excitement of being in the business, but you still have your privacy!

(Jennifer O’Brien)

Oh yes! I get to travel, and do what I love to do and get paid for it. All I have to do is show up and sing. It is the best of both worlds for me!

(CSC) 11. When you’re not working, what do you enjoy doing most on your free-time?

(Jennifer O’Brien)

Well I am involved with my church, and I love to walk in the woods. I’m really kind of a boring person. (Laughs) I love my home, love being home, and love small groups. I’m more of a one on one person. If I get into a big crowd of people I can fade into the sunset real quickly. I’m working a lot lately in the studios and that keeps me pretty busy. Time just goes, and I don’t know where it goes to.

(CSC) 12. How does the session work that you involve yourself in come together?

(Jennifer O’Brien)

Its different things; it can be with a solo artist or a group. I’ve done a lot of work with Bill Gaither (Gospel) in the past. That’s one of the downsides about being out on the road so much; even when you’re home people just assume you aren’t in town. That’s hard because it does conflict with your session work but figure I gain so much more than I lose when I’m working with Dolly!  

(CSC) 13. When you’re going on the road, what are THREE things that you can’t leave without?

(Jennifer O’Brien)

Makeup, Warm clothes, because some people like subzero temperatures, (Laughs) and my bible. Life on the road is like one big extended family because we’re together so much.

(CSC) 14. What is the daily routine like for you when you’re on the road?

(Jennifer O’Brien)

You get up and get ready to head to the venue around 3:30pm for the sound check. Then afterwards we head to catering for dinner. When we were in Europe we had our own personal caterers that traveled with us for the entire tour. Upon arriving in each town, they would head off to the local market and purchase an arrangement of fresh organic meats and vegetables. It was some of the BEST food that I’ve ever eaten and always consistent!! A smile comes to my face whenever I think of them. After dinner it’s time for hair and makeup. We had our little brother (Steve Summers) fix our hair every night, how spoiled can a girl get! Then it’s time for the show, and we head towards the stage and are in place about ten minutes before show time. The moment they see her, for the next hour and a half to two hours, they belong to her!

(CSC) 15. What motivates you?

(Jennifer O’Brien)

God!! I feel so blessed to have been able to live out my dreams. I love to sing, love to travel, and I just wake up every morning and thank God for another day.

(CSC) 16. You mentioned that you are involved in your church; do you get to sing with them in the choir?

(Jennifer O’Brien)

I sang in the choir for eighteen years. I go to a large church in Nashville and we’ve done some recording and TV appearances with Dolly actually (Christ Church Choir). I was very involved in that for eighteen years, and then got out of it a few years ago. I may go back to it one day though, who knows…

(CSC) 17. Out of all the beautiful countries you traveled to this past summer with Dolly, did you have a particular favorite?

(Jennifer O’Brien)

I don’t know I loved them all; I want to go everywhere. They talked about us possibly going to Australia one day, and I’ve always wanted to go there, so hope that will come true one day! We were actually going to go to Australia with Kenny Rogers back in the early 90’s, they were booking it, and then something happened to their economy so it ended up not working out.

(CSC) 18. What is the experience like for you performing on major television shows such as Jay Leno, American Idol, Dancing With The Stars, and Ellen?

(Jennifer O’Brien)

The first thing that comes to mind is every studio that we visit is so much smaller than it appears on television. Some of them are extremely cold during sound check (David Letterman likes to keep it at 49 degrees). We’ve always been treated so well, and it makes me realize that they are just people doing their job, just as I’m doing mine!    

(CSC) 19. Lastly, what would you like to share about yourself with the readers of this interview?

(Jennifer O’Brien)

God has been so good to me. He has allowed me to live a life most people only dream about and there is no telling what the future will bring. It’s in his hands….right where I want it.

Make sure to check out pictures from our interview below;