Pitch Perfect

By Harrison Pierce

Originally published on Advocate.com July 28 2009 11:00 PM ET

Famed rap mogul Sean "Diddy" Combs has been turning aspiring musicians into music superstars for four seasons on his hit MTV reality series Making the Band . Among the better known products of the Diddy star-making machine are the hip-hop group Da Band, platinum-selling female group Danity Kane, and the award-winning R&B group Day26. For the show's fifth season, the Grammy-winning producer is on a nationwide hunt for backup musicians to join him onstage during his upcoming Last Train to Paris tour. Naturally, the king of moniker changes has renamed the season Making His Band to underline the fact that, yes ... this time the search is personal.

On Monday night's premiere episode, singer Jaila Simms emerged as one of the show's strongest -- and most controversial -- contestants. A powerhouse vocalist from Chicago, Jaila appeared early in the show, insisting that talent should matter more than a contestant's "story."

Nevertheless, Jaila's story -- specifically that she's a transgender woman -- quickly came to the fore during her Los Angeles auditions, in which she wowed Diddy with her soulful rendition of Estelle's "American Boy." Nevertheless, the Bad Boy Records impresario didn't fail to notice that Jaila's range ran suspiciously low. Fortunately for Jaila, Diddy's only concern was that she lose her "toe-up weave" before advancing the singer to the next round. In the coming weeks, we'll see if Jaila's natural talent prevails in her quest to become a unique and groundbreaking member of Diddy's band.

The diva-in-training talked to Advocate.com about her reality television debut, growing up transgender in a devoutly religious African-American household, and what she'd rename Diddy if given the chance.

Advocate.com: Jaila, tell us how you came to be involved inMaking His Band.Jaila Simms: I've been a fan of the Making the Band the series as well as of Diddy for years. When the opportunity came along, my girlfriend was like, "Hey, why don't you go audition? He's looking for background singers for his band." When I realized it would actually mean working with Diddy on his music, I couldn't pass up the opportunity to audition.

What was the audition like for you?The initial audition was in Chicago and it was a pretty lengthy process, weeding out people who actually had potential to be in the band. I really, really enjoyed meeting some of the judges there as well.

What did you sing at the Chicago audition?There was a list of songs we were able to choose from. For my first audition I sang Kanye West's "Heartless."

What was it like meeting Sean "Diddy" Combs for the first time?Intimidating. Intimidating, like ... I don't think I've ever experienced anything like that. I walked into the room and he sucked the life out of me. It was just, like, that kind of emotional, cathartic moment because everything I'd worked so long for was actually coming to fruition, with just one man in a room. It was then great to see him actually working on his own music and to see that he is an artist and has the same struggles everyone else faces. You know, he cries, he bleeds, he gets frustrated at times.

Did he give you valuable advice on making it in the music business?Definitely. You know, it was all about the live element with Diddy, and he definitely taught us valuable lessons throughout the entire process. One thing that stood out to me was, you know, to leave your heart on the stage. When you go up there, give your all to the audience because they came there to see a piece of your soul and that's what you want to give them. Diddy showed me how to do that as a vocalist.

Did you get along with the other contestants?Loved them [ laughs ]! No, of course any time you have 40-some-odd musicians and vocalists in a house together, it's definitely going to be a colorful event, to say the least. But the journey was great, and I wouldn't change the [ Making His Band ] family for anything.

What was the most challenging moment for you during the series?There were several challenges, and we were on pins and needles the whole time because this was our careers on the line. You don't want to mess up ever! A lot of [the challenges] were facing our own fears and overcoming our own insecurities. We had to always put our best foot forward for the judges as well as for Diddy.

Did you always want to be a performer?I did [ laughs ]! Ever since I was a little one. A little tot. I knew that music was my passion and my purpose for being here on this planet. I really feel like we all have a divine purpose, and, you know, at some point in our lives it's revealed to us. Luckily for me, it was revealed at an early age, and music was it. I knew that stepping into the music industry was going to be hard, but I've always known that music was my love.

Growing up, who were your musical role models?Of course Whitney Houston and legendary figures like Michael Jackson. I'm also a big musical theater buff, so people like Bette Midler or Liza Minnelli or Judy Garland as well as pop icons like Anita Baker and Mariah Carey -- they all influenced me. And of course, I've got to give a shout-out to Prince because he is iconic. And, of course, Diddy and the whole Bad Boy family.

Did you have any transgender role models?Hey, not really. I'm 27 years old, so I was growing up during the '80s. I was an '80s baby and there weren't too many transgender people in popular roles in the media. Just recently, I've been looking up to people like Laverne Cox and RuPaul, who's a female impersonator, but in the same vein. Also, people like [ America's Next Top Model transgender contestant] Isis and people that I can connect with on a personal level who are more in my generation.

Was your family supportive of your "coming out" as transgender?I feel like, with all the things I've gone through, my family has definitely been there for me and what's really important in our family is love. People can judge you -- society, even your friends on some occasions. But your family will always be bound by love. Growing up as a child and knowing that I might be more comfortable living my life another way, um, is definitely rough. But if you do have that kind of love in your life, you understand that they're going to love you no matter what.

So they didn't force you into therapy?This is the whole thing, and I'm gonna keep it all-the-way real. I come from a black family that was born and raised in the church, so we're deeply rooted in religion and in "doctrine," but at the same time, there has to be a balance. My family, for instance, may not have always accepted me and may not have always liked my actions, even so far as my putting popcorn in the microwave instead of on the stove. But at the end of the day, we know that our love for each other supersedes that. If more people take that into consideration, you'll have a lot less therapy patients.

What do you think is the biggest misconception about transgender people?A lot of people look at transgender women as people who are overly sexual, especially in the LGBT community. I think people don't understand that we're just trying to have our outsides match our insides. It's more than about sex. On a spiritual level, some people think their soul is caught in the wrong body. They're just not able to be themselves. And I want society to know that it's not based upon sex or image or wanting to be beautiful. It's about wanting to be who you truly are.

How would you define your sexuality?I'm a heterosexual woman [ laughs ]! At least that's what I think in my own head. Now, what the boys think may be something totally different, but that's how I feel.

In addition to singing, you also model and act?I model as a full-figured model, yes, and I'm a trained actress. I went to the American Musical and Dramatic Academy and studied musical theater, so I'm working on some endeavors in that light, but right now I'm just so focused on, you know, enjoying this ride.

Any plans to move to Hollywood?If somebody called me and said, "Hey, girl, we want you to come to Hollywood," then I'm on my way! Tonight's the premiere of the show, so I'm just gonna enjoy being at home with my boyfriend and my family and taking it all in. I'm hoping that, with a lot of the things I have in mind and some of the endeavors I want to pursue, that I'm gonna be away from home for quite some time. I'm trying to enjoy the time I have here [in Chicago] for now.

If you could give Sean Combs yet another new name, what would it be?Big Daddy Diddy [ laughs ]! He's such a father figure -- you see him playing with his children and the way he speaks to everyone else. He takes that paternal role in any situation. Yeah, he's Big Daddy Diddy to me.