Kiley Dean Began As Britney Spears’ Backup Singer. She Ended Up Finding Herself

Rolling Stone interview series Unknown Legends features long-form conversations between senior writer Andy Greene and veteran musicians who have toured and recorded alongside icons for years, if not decades. All are renowned in the business, but some are less well known to the general public. Here, these artists tell their complete stories, giving an up-close look at life on music’s A list. This edition features singer Kiley Dean.

When Kiley Dean was little, her parents took her to see Elton John, New Kids on the Block, and Milli Vanilli when their tours came to her hometown of Orlando. “I would cry when the stage would open and the music would hit your chest,” she says. “I’d have tears rolling down my face.” And when she was a little older, she won front-row tickets to a Spice Girls concert through a radio station contest where she sang like them on the phone. “We were sitting really close to the subwoofers,” she said. “I remember that emotional feeling of ‘I belong here.'”

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Her dream came true within a couple of years, when she was tapped to sing background vocals for Britney Spears’ first headlining tour in 1999. In the years that followed, Dean inked a solo deal with Timbaland, recorded with Bubba Sparxxx and Flo Rida, and hit the road with Madonna, Matthew Morrison, and New Kids on the Block.

All of this was possible for Dean because she possesses an incredible voice and natural ability to blend with others. “There are people that are born with something special,” she says from her home in Nashville. “I’m for sure one of those people. When people ask me, ‘How do I become a better singer?’ I say, ‘It starts in your ear.’ If you can listen to something and you take it from your ear and emulate it through your mouth, that’s when you’re a singer.”

Dean was born in Arkansas, and can remember standing on a fireplace belting out “Tomorrow” from the musical Annie to her family when she was two. “My mom never pushed me,” she says. “She was the opposite of a stage mom. She did know, however, that I had something at a very young age.”

Her family moved to Orlando when she was six. As the years went by, Dean became infatuated with Mariah Carey, Whitney Houston, Taylor Dayne, and Polish pop star Basia. She spent countless hours trying to emulate their singing styles, and she further honed her voice in the choir of her megachurch. Around this time, she enrolled in the same Sunday school as a Louisiana-born singer/actress named Britney who had moved to Orlando to perform on The Mickey Mouse Club, though they wouldn’t formally meet for a few more years.

As high school came to an end, Dean had absolutely no idea what to do with her life. “I remember sitting in Marine Biology my junior year,” she says. “Everybody was looking at colleges. I was sitting there like, ‘Oh my gosh, what am I going to do?’ I was literally praying, ‘God, what am I going to do? I don’t want to go to college. I want to sing.'”

Her prayers were answered during a Christmas performance with her choir. “This guy, Mark Goff, was in the audience,” she says. “He was Britney Spears’ vocal coach. He heard me and was like, ‘That girl is amazing. I want to take her under my wing.’ He wound up actually getting me the audition for the Britney Spears gig.”

That gig catapulted Dean into the world of pop music. And nearly a quarter-century later, she’s still there.

Do you recall first hearing Britney Spears’ music?
Oh yeah. It’s so funny. I was like, “Whatever. This girl is lame. I need to be in her spot.” In high school she was out there doing it. But then I met her and I was like, “This girl is phenomenal.” And I fell in love with her. She’s just an incredible human being.

Tell me about getting the job.
Mark Goff called me while I was at Disney with my family. He says, “Hey, I have an audition for you. It’s with Britney Spears.” I was like, “That’s crazy!” I literally left Disney and ran to the audition, sang for [Spears manager] Johnny Wright, met Brit, and got the job. I left my senior year of high school to start this crazy year of stardom.

Was this after she opened for ‘NSync?
Yes. This was her first official [headlining] tour.

Tell me about preparing for the show. She was just exploding at this point.
Preparation was very minimal compared to … fast-forward ten years to Madonna. I didn’t know that, though. I’m a kid. Everything is fun. Everything is new. I’m so green. It felt like easy-peasy. We rehearsed for maybe two weeks. Then we go out and do this tour. It was wild. We were playing amphitheaters and fairgrounds.

The tour started in Pompano Beach in June 1999. Do you remember that night?
Yes! It was all little girls and their parents.

What was Britney like back then?
This is true today — even though you can see she’s struggling in a few ways, she’s truly one of the most precious human beings I’ve ever known.

You traveled together in the same bus?
Yeah, on the first tour. It was awesome. We were all a little family. It was Britney, the other background singer, the dancers, and me. We were all really, really close. It was just wild. Everyone was like, “Do you miss your life back home?” I was like, “I’m sorry, what? This is my life now.”

What’s it like to walk onstage and see thousands of children just screaming?
It’s wild. And it was weird. I was like, “Wow, I want this for me.” But it was really cool since you get to see how other artists handle stardom, handle not being phased by that. I would have dropped to my knees. It’s crazy to be able to watch my peers go before me and see how they handle it. She held her place really well..

She was a teenager, and the spotlight was so intense on her. She was really poised though.
Yeah. I think she did a good job being so young and getting really inappropriate questions asked to her about her personal life. That would have driven me crazy, but she held it together really well.

This was in a lot of the recent documentaries. It’s this 17-year-old being asked pervy questions about her body by adult men. It’s crazy when you look back.
It’s disgusting, honestly.

You played a lot of state fairs. What were those like?
I just remember the smell of cow shit when you’re singing onstage. That was the grossest, strangest thing. That was a really quick turn, though. By the next tour for Oops!…I Did It Again, we were playing arenas, and that was never an issue again.

Tell me about preparing for that tour. Suddenly it’s a much bigger production and she’s flying around on a magic carpet. You really scaled up.
We did a lot more promo for that one. You get bigger, you bring in the bigger choreographers like Jamie King. The stage is bigger, the arena is bigger. We weren’t standing in the background anymore. We were dancing and singing with Britney. It was fun. I never remember it feeling like work.

There were so many big opening acts. Did you spend time with LFO or Aaron Carter or Destiny’s Child on that tour?
We did. It’s crazy to think about being in close proximity of these people and getting to know them in a level of normalcy. When you’re backstage with these people, all fame goes away and you’re all on the same playing field.

How did Britney impress you just as a dancer?
She was great. I’m not a dancer, so that doesn’t really excite me. I’m not into dancing. But her choreographers really knew how to choreograph her body. I think that’s what people loved the most.

As the tour is winding down, are you starting to think about getting your own career going?
Actually, I met my manager in a hotel lobby. He was the A&R for one of the opening acts, Michael Fredo, who is Tommy Hilfiger’s nephew. He was on Warner Bros. He heard me sing in a hotel lobby and went, “Oh my gosh.”

From that point, he took me under his wing. From there, I did the Grammys with Britney and I met Timbaland in a hotel lobby at like 2 a.m. That’s where my relationship with Timbaland hatched.

What was his idea for you?
He freaked out. He was like, “I love her, she’s great.” At that time, he didn’t have a label. He was like, “I want to work with her, but I don’t know how.” At that time, he had Missy Elliott, Tweet, Aaliyah. He had all these deadlines. People were always on his heels since he’s the best.

I leave Brit. I fly out to L.A. I start living out there. Slowly but surely, I start meeting people in the industry. I start working out there. My manager would be like, “You don’t remember working with Tim and Bob?” But I didn’t. It was all happening so fast. I came up with so many people. It was a whirlwind.

We did a cute little pop demo. I started getting a lot of, “This girl is really good. I want to meet her.” They would see me and they’d be like, “Oh, you’re white. This doesn’t make sense to me.”

Especially at this time in the music industry, there weren’t white girls doing the music I was doing. You had Fergie, but Fergie is Fergie. You had Joss Stone, but she was doing neo-soul. Nobody was doing these hip-hop beats.

Anyway, I’m jumping ahead. I did a demo and I was going to sign. In 2002, he did a label deal with Interscope under Jimmy Iovine. He signed me there [to Beat Club Records]. That’s where my album Simple Girl was born.

Your single “Make Me a Song” hit Number 99 on the Hot 100.
It was absolutely incredible. We were right there. I mean, we were right there. [Sighs.] This is where politics enters. I’m just going to be an open book since this is the true story. I just adore Timbaland. He’s done this album for me. It’s the perfect album. It’s before its time. It’s literally a door-opener. We’re taking off. And the head, Jimmy Iovine, comes to my rehearsals. He caught wind of who I am, what I’m doing, what kind of performer I am. He’s like, “Oh shit, I gotta get down and see her.”

He comes in and sits down. I was filming one of those MTV You Hear It First videos. And everything stops. He wanted to take the reins and have Ron Fair come in and recut songs and make me into something different than what Tim and I were doing. He wanted us to change lanes. It ended up completely messing and destroying what we had made.

Did he want you to be less R&B and more pop?
He wanted me to be more white girl. “There’s a lane, let’s fit in that lane. Let’s play it safe. Let’s not take risks.” It was devastating, to say the least. Tim was pretty hurt by it, but Jimmy was at the top. I have nothing bad to say about anybody. I’m over that. I’ve had therapy, all those things. But it was devastating. We were lane-breakers. We were starting something that would, in a few years, open a lot of doors for a lot of artists.

You cut the whole Simple Girl record, and it just doesn’t come out?
Yeah. Brutal. This year marks 20 years. Isn’t that crazy?

At least “Make Me a Song” and “Who Will I Run To” came out.
Those two songs were my absolute least favorite. “Who Will I Run To” was my Number One least favorite out of the whole album. The deep cuts we had like “Kiss Me Like That” and “Cross the Line,” they are still relevant. That’s what’s crazy.

That year, Timbaland said he was going to record a big “We Are the World”-style song with Missy, Justin Timberlake, Bubba Sparxxx, and you, called “The World Is Ours.” It never came out, but did you ever record it?
No. I actually don’t even remember that. I probably would have gotten off of Interscope by then. I remember Tim being pretty heartbroken about the whole thing. Politics suck and they’re in every business we have. Growing older and seeing that, now I realize. It still doesn’t negate the fact that that really blew.

I imagine Jimmy Iovine looked at you and thought, “She should be on TRL singing like Britney Spears.”
Exactly. That was the curse of working with Britney. I would go into meetings and they’d go, “You’re not Britney.” I wanted to be like, “Are you kidding me? Why do you have a job? Aren’t you supposed to break artists?” This is from a day and an age where they actually had artist development. They would look at me and go, “Well, you’re not really like Britney.” I was like, “Oh my God.”

That’s the industry — when something comes along that’s new and different, all they think about is cloning it as fast as they can. You had Jessica Simpson, Mandy Moore, even Hoku all being pitched as the next Britney.
You took a girl that could barely sing, that’s very cute and could dance her butt off, and it worked. Her timing was perfect. She was lovable. But it wasn’t about her voice, and we all knew that. That’s fine. That’s OK. She worked. It really is about timing. She stepped in at the perfect time.

You were on the 2004 Bubba Sparxxx song “Nowhere.” How did that happen?
Me and Bubba were labelmates. He was always in my world, whether it was in a video or just at the office or gatherings we would have. I think we were in in New York and I was cutting a few things with Petey Pablo. It was just kind of organic since we were on the same label. I think it wound up being his favorite cut off that album, and a lot of other peoples. It was just really an emotional side of him that he was really stripped down and raw about. People appreciated that.

There was a brief period in 2005 where you were billing yourself as Blue Eyes. What happened there?
I didn’t understand that. That was my manager’s thing. I think he wanted to put out music without people knowing it was me since our past had been… In all honesty, after we left Interscope, nobody wanted to sign me. Nobody. Without saying too much, it was like, “If Jimmy can’t break Kiley, nobody can break Kiley.”

That’s how it was. I have no fear of saying how it was. People know the industry is dirty sometimes. It was a control thing. They had the control. I had none. If I wasn’t going to do everything their way, then there wouldn’t be a way.

A few years later, in 2008, you were with Flo Rida on “Elevator.”
I think I was on tour with Madonna. He called me into the studio real late in Miami and was like, “Come jump on this song.” We always had a good rapport. I always have love for him. I love him, love his family.

In the years before Madonna, around 2006 and 2007, how frustrated did you feel that things just weren’t happening?
Complete depression. I don’t know what it is about the industry. And this was before TikTok and all this ridiculousness we have now, all this social media. You really have the path to power if you want now. Back in the day, you were very small. Few and far between even got noticed by a label. To even get your foot in the door was, “Wow!”

We had come this far, and were damn-near blackballed by the industry. We just couldn’t figure out how to make things work. I was the most depressed ever. I was like, “Now what am I going to do? I’ve left high school. I have no idea.”

I was literally praying. I was like, “God, if you want me to stay in this industry, you have to drop something from the sky. I’m literally packing up my apartment and leaving L.A.” I remember just being the lowest. I was so emaciated that the wind would blow me over. It was just crazy.

And I get this call from ‘NSync’s musical director I had met 10 years earlier. He goes, “Madonna needs a new singer. We need you to come in quick since we’ve brought in some girls and they’re not cutting it.” I went in and I killed it.

How did you feel when that phone call came in?
I dropped to my knees. God was like, “There you go. Come on!” I knew at that point I was still able to use my gift. It just gave me faith. It restored my faith since my prayers were like, “Anything, God.”

What was it like walking into that rehearsal room? It must have been intimidating.
It wasn’t intimidating for me. I guess it’s just part of the world I grew up in. I walk in with these heels on and I own it. But she carried this really heavy, strong — as tiny as she is, she carries a very strong presence. I remember being like, “Oh damn, that’s Madonna.”

The first thing she said to me was, “Take those damn heels off.” [Laughs.] I’m really tall and I had these heels on. But I went in and killed the audition. And then I was her background singer for many years, the next three tours.

Tell me about rehearsals with Madonna. This is a really big show.
I have never in my life worked with anybody who rehearses like this woman rehearses. It is wild. Even now, she’s going out on tour and, I believe, her rehearsals will start in February. She doesn’t go out until July. That is five months of rehearsal!

Some people love it. I do not like the rehearsal process at all. But it is wild. I’ve never seen somebody with a work ethic like that. I was like, “This is what it takes to be great. This is what it takes to be on the level that she’s at.”

She had a hand in every single decision, down to the eyelashes that we wore. I swear. I kid you not. She would come up and look at my outfit and go, “What lashes are those?” I was like, “Oh my God. This woman is amazing.”

We started out with just the band. Dancers do their thing in a whole other area. And there was a couple of months with just us. Then it turns into production rehearsals where where we all meet to put the show together. And she comes in and works with the band for a couple of hours. Then she peaces out and goes and works with the dancers. This woman is unreal. She goes into a whole different room and starts dancing. I’m like, “Oh my God.”

Slowly by slowly, bit by bit, this absolutely massive production comes together. And then we’re in Cardiff. That’s the very first show I did with her. The curtains drop and we’re in a stadium. I’ll never forget it. Every hair on my body stood up. I’d never experienced power like that.

We’re talking about 60,000 or so people all pushing their energy towards where you are standing.
Yes! That is such a great way to put it. I’ve never heard it like that. And you feel it in the core of you. It’s wild.

The other backup singer was Nicki Richards. How did you two work together?
Very professional. We were very independent, but we come together and blend really well.

What were your favorite songs to sing?
When we did “Take a Bow” in Macau, China, I was like, “This is next-level.” That was one of my absolute favorite Madonna songs. As little or big a fan of Madonna as you are, you’re going to know her music. She’s going to have touched your life in some way, shape, or form with one of her songs.

I think the coolest part is hearing her sing “Borderline” or “Lucky Star” or “Open Your Heart.” Those are always the ones where I’m like, “Wow, I forget how many years she’s been around, and how massive her hits are.”

She can dance two hours and still sing that well. It’s a real athletic performance.
Of course. And behind the scenes, she has her workout regime. She’s just an all-around perfectionist. That’s what she is. It works for what she is.

What’s it like to travel by private jet and stay at the best hotels?
There’s a lot of tours I’ve turned down after working for Madonna. It got to the point where people stopped asking me. The first tour we did was my favorite since there’s something about the first time doing something. You don’t know what to expect. And then every expectation is higher than what you thought. It’s like, “Wow.” So Sticky and Sweet was hands down my favorite tour.

What were you doing in the downtime, say, when you were in Spain or wherever for two days between shows?
Absolute exploration. I saw places I otherwise never would have seen. It’s like putting your finger on a map. For instance, we went to Oslo and had a bunch of days off. I just remember exploring this unbelievable place. It was like out of a storybook. I would have never chosen to go there, but it was phenomenal.

With the MDNA tour in 2012, did you have to re-audition or it was just yours?
It was mine. That’s the thing with the industry. It’s so weird. Right now, I’m doing a lot of vocal production. It’s so funny when people say, “Send me a one-sheet.” I’m like, “What?” If you know, you know. I’m not used to the auditions, “tell me what you’ve done” kind of thing. But I’m in a new city now.

Was MDNA the same thing with the long rehearsal period?|
Oh yeah. And when we got to production rehearsals, we would run the set twice. It was wild.

What are your standout memories from that tour?
On that one, I became a little more open with the people I worked with. On the first tour, I was a little more closed-off. On this one, I befriended some of the dancers. I’d go out in these foreign places and just have a good time. That’s mostly what I remember. And working out a ton.

Singing “Like a Prayer” every night must have been really uplifting.
It was amazing.

And even lesser-known songs like “Masterpiece.”
She had some really cool songs on that album. I like “Masterpiece.” I really like the piano one she did from that movie. She had some good songs on the record.

I just can’t imagine standing onstage and singing “Vogue” in front of all those people.
Yeah. It’s crazy. That’s partly where the rehearsals come in. You do it so many times that you’re a little numb to it, until you get onstage and see people’s reactions. Then you’re like, “Oh yeah, we’re singing ‘Vogue.'”

By the time of Rebel Heart in 2015, is this just old hat for you? It’s just become your life.
Totally. That was probably my least favorite tour, if I’m being honest. It was just where I was. I wasn’t in the space to tour anymore. I was ready to settle down. I got married on this tour. He proposed at the beginning of the tour, and we ended up getting married on a day off in L.A. in a chapel. I finished the tour, but I was ready to be done with that chapter of my life.

You did 82 straight concerts.
It was a lot. And she was going out really late. She was going onstage two hours late. I’m not…it was just wild. People were getting angry. I was tired. I was tired. That’s me personally, though. I still love her. I love everyone I worked with. I was just done.

The last show was in Sydney, Australia. Did you think to yourself that night, “I’m done with this forever?”
Yeah. I did. I knew what I wanted to do. I knew I wanted to have a kid. I knew I was done. And mind you, this tour was over a year long. If we count Grammy and Grammy prep and the Brit Award prep, we started in December of 2014. I didn’t get off the road until April of 2016.

It took a lot out of you, but it gave you so much also.
Of course. The three years that she takes between her tours — that’s the time to get rejuvenated and want to go back out again. When that phone call would come, I’d be like, “Heck yeah, I want to go. I want to go!” But when life changes so much, that’s not even a thought in my mind anymore.

To go back a bit, how did you get on the New Kids on the Block tour with Matthew Morrison in 2012?
Oh my gosh! That was the best tour ever. So my buddy Kevin Antunes, who is the musical director for Madonna, called me up. He said, “There’s this guy Matthew. I think you guys would gel really well. He’s awesome. Do you want to do this little promo tour he’s doing?” I was like, “Of course. Yeah.” I ended up falling head over heels in love with this guy, just not in a romantic way. Just as a friend.

He’s the most incredible human being, love working with him, so talented. As I’m working with him, we pivoted and he went, “We’re actually going to open for Backstreet Boys and New Kids on the Block.”

We get out there. It’s kind of like the Tiffany effect, where she had New Kids open for her, and the fans were like, “No, we want New Kids.” It didn’t happen that intense. People obviously want to see New Kids. The women were like, “Whatever, we want New Kids.” And then Matthew would get out there and start doing his thing, and they would be wilding out.

He’s like this crooner that dances. He’s just amazing. We fell in love with the New Kids. This other background singer Kamilah [Marshall] and I wound up doing this thing called New Kids on the Block Update. The guys got wind of it and just loved it. It was phenomenal. It was so much fun.

I saw the video where Jordan Knight is bringing you your coat.
Yes! It was a blast.

The Blockheads are intense. They really love the New Kids.
That’s what happened. They found us. We were being so ridiculous with our over-the-top shenanigans on our video posts. They found us and they told the guys, “You need to go find those girls. They are hilarious.” It just snowballed after that. It was so much fun.

You were a childhood fan of Donnie Wahlberg. What was it like to get to know him?
It’s so funny. He is so down-to-earth, and just a good human. Sometimes I’m afraid to meet people I look up to if that’s not the case. But it’s so nice to meet people… Drew Barrymore is one of those, too. I was like, “I don’t want to meet her.” But she ends up being the sweetest thing you’ve ever met. All of them were so sweet and so kind.

How was the atmosphere different than the Madonna tour?
I think men, in general, hold a different energy than women, especially women who are solo. Men, in general, especially if there’s numerous men, are just a little more laid back. Not even men… Just a group. It’s not all on one person. It’s on five of them, so they’re naturally just a little more laid back.

I’m sure it was weird to go back to Madonna after that, since she’s less laid back.
Yeah. That’s not very laid back at all. Our soundchecks were like shows. That’s the reason she’s at where she’s at. She wants things perfect. If she’s missing something, she wants to make sure that she gets it. That takes time.

What were your goals after the Madonna tour finished?
Honestly, me and my husband got pregnant like three months after I got home. What I wanted to do was actually take some time off. Touring for that long, every night getting some sort of dopamine hit… The curtain drops and you’re on a high. Having that for a year is really something. You have to come home and decompress for a minute.

We got pregnant. We bought a house and were moving into this home. I just wanted to be domestic for a little bit. We weren’t planning on getting pregnant so quick, but we did. We were like, “Oh my gosh.” We always talked about not wanting to have kids so far from our family. And when we were on tour, we were talking about moving to Nashville. We ended up settling in L.A. since we both worked there.

But we made a really hard decision and sold our house a year later. We moved to Nashville. I knew it was going to be hard, but I also felt like, “I’m Kiley Dean. Everyone is going to…” But that wasn’t the case. Back up. We sell everything. We take this six-week-old baby on a plane and move to Nashville. We completely uproot our lives and move to a foreign, southern city. It’s been wild. It’s been just the most different lifestyle that I’ve known.

How did you establish yourself there?
I’m in the process of doing that now. When I moved here, I was turning down tours. I turned down a couple of really big artists.

Are you able to say who?
Janet Jackson. Matthew Morrison. These were things I didn’t want to do anymore. I had this baby. I said out loud, “I want to take two years and just solely focus on my child.” And I did that. And right when I was ready to get back to work, I got cancer.

That put me out for a while. I just remember Madonna going back on tour that year. I remember kind of being like, “I want to go.” I got that itch. She ended up hiring my girl, who I love, Latrelle Lanz, “Munchie.” She has a similar story. Her story is with Neptunes. I remember being like, “I don’t want to go since I don’t want to leave my daughter. Something else will come my way.” And it was cancer. I was like, “Daaaaamn.” And so 2019 and 2020 was me battling that demon, battling that gross, awful thing in my body.

I’m sure in some ways, you came out stronger on the other end.
Yeah. But it was brutal. There were constant complications. I was wheeled out on a stretcher because I went into anaphylactic shock twice on chemo drugs because my body was just not having it. I stopped breathing. They were straight up like, “This girl is going to die.”

What gave you the strength to get through those moments?
God. There was a peace that was out of this world, I guess you could say, when these things were so terrifying that I could not even begin to describe. It was this wash of just peace. That’s when I decided to do a Christian gospel EP. I don’t want to be a Christian music artist. That’s not my goal. I just wanted to put this music out to show people that I could not have done this without God.

One of the songs I wrote was “All Along.” It starts out with “In the quiet/In the dark/I lost the beating in this heart/And what I imagined in my arms so quickly fell apart.” I’m talking about my miscarriage. I was pregnant when I was diagnosed with cancer. Right before my mastectomy, I lost the baby at Publix [grocery store].

I’m so sorry.
It’s OK. I actually have therapy in 30 minutes because this is something that I wasn’t able to mourn. I had to put my boots on and walk through the fire. I didn’t get to cry about losing the baby, so I wrote a song about it. And I’ll be crying in therapy later. But God knew just because it was happening to me, doesn’t mean it’s happening for me. It’s to help other people. I get to talk about it and help other people through it.

I can’t tell you how many women have called me and said, “I’m terrified. I got diagnosed.” I said, “OK, this is not a death wish. Let’s talk about it.” I get to help people. This is not something you’re thinking when you’re almost dying on a gurney trying to breathe, but that’s how God used me. I was a tool.

Your song “Overcome” was clearly inspired by this.
Yes. And you don’t need to be super-uber-spiritual. I’m just spiritual. I love God. But you don’t have to have that relationship. It helps if you do. But you can still hear that music and go, “That’s really inspiring.” I’m not tooting my own horn at all, but that’s some inspiring shit. If you can come out of that and write a song about the hardness, that’s where the best songs come from, what you’ve walked through. Bad things will happen. We will get through them. We will overcome.

You shared your story in People. I’m sure you got a lot of great feedback for that.
Yeah. It was wild. I had the girl calling me. We did the interview over the phone. She was crying. It’s a crazy story. It’s wild to be on the other side of it. I was at church the other day, and my pastor was just up there killing it, giving this sermon. He was like, “Sometimes things in life don’t go the way you want. You get that call that cancer is back.” I was like, “You did not just say that.” But he’s right. We get things in life that hit hard. But we don’t have a choice. We have to walk through it. We can either do it alone or hold God’s hand. It’s way better.

I went up to him after the sermon. I was like, “Were you looking at me when you said that?” He was like, “No, never.” But the reason I say that is because that’s a real fear of mine, having a child and getting the call, “Kiley, it’s back.” He held my hands and he prayed over me. There was that peace again. Worrying won’t add another day to my life. I have to let this go and just live.

I saw all those cover songs you did on your YouTube channel. I’m sure it was fun to revisit “Baby One More Time” and “Like a Prayer,” which you originally sang as a background vocalist.
Yeah. It’s really cool. I love what I did with “Baby One More Time” since it was really different. But I’ve kind of taken a break overall from doing the whole artist thing. I’ve really sunk my teeth into vocal producing. I have so much to offer other artists in their journeys. I know how hard it can be, how intimidating it can be, and vulnerable, especially if you wrote a song or you’re singing a song that means something to you. It can be vulnerable to deliver the song in the way you really want to get across. I’m just there to help other artists sound like the best version of themselves. I always had a vocal producer, and I’m really good at that, so that’s the next shoe I’m stepping into.

You were with Britney Spears at a really pivotal point in her career. Do you ever get approached by filmmakers or writers that just want you to spill dirt on her?
I would never. And they haven’t. I would cut that down real quick. I would never spill dirt on Britney, Madonna, or anyone I’ve worked with. That is a precious, sacred thing. I think especially of Madonna’s children. I know her children. I would never say anything negative, and I don’t have anything negative to say. But even if I did, I wouldn’t do that. I’ve looked in her kids’ eyes. I’ve seen the vulnerable sides to these women, and I’d never do that.

If you were offered the chance in the future to do a big tour with someone like Madonna or Janet, would you consider it?
No… Let me not say “no.” If it was a residency, I could wrap my mind around that. But touring the world right now … it’s just not … I don’t think so.

You’ve done it at the highest possible level. There’s nothing bigger than a Madonna tour.
That’s the thing. Let’s go out on a high. I think that’s where I’m at. Let’s leave it there. It doesn’t get bigger than her. It doesn’t get better-paid. Let’s leave it there. Now, there’s other things I could do. I could vocal-produce a tour or whatever, but we’ll cross that bridge when we get there.

Do you think you’ll return to the artist thing in the future and record more songs?
I don’t think I could ever be officially done. Right now, I’m more behind the scenes. I wrote a song just yesterday that’s going to be phenomenal. But I’m more of a writer/vocal producer now.

I’ll wrap in a sec, but it would be great if Simple Girl could finally come out this year considering it’s the 20th anniversary.
Can you imagine? Can you imagine? It’s just sitting on a shelf somewhere. Nobody gets to hear it. It’s just sitting on a shelf somewhere. It’s the saddest thing, and that happens to so many people.

Last thing… If you could speak to yourself at 17 when you were on that Britney tour and just starting out your journey, what advice would you want to give her?
That’s a really good question. “Be strong. Take courage. This is going to be really hard. This is going to be a hard road to navigate.” [She starts crying.] This is making me emotional. I would tell myself, “You’re good enough. No matter what people say, you’re good enough. Don’t let what they say change you. Don’t take 20 years to get yourself back.”

I’d say that to any young girl. I think I’m emotional because I have a young girl now. And the men in the industry… I’m not even going to go there. I could. Trust me, I could. But the despicableness of the men that want control, how they control women, back when I was young… Timbaland was never like that. He was so good to me. He was a brother. I’ll love him forever for that.

But just the things that would come out of these grown-ass men’s mouths was despicable. That stays with you. Nowadays I think people are a lot more awake to that. Men are having to watch their mouths about what they say and how they say it, but I was one of the ones that got that all over me. That’s why I would say, “Take courage. Stand the hell up for yourself. Don’t move for anybody.”

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