Jeff Pearlman

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Kay Hanley

#121
The former Letters to Cleo singer talks about life in the spotlight, life in recovery and life as the musical force behind ... Doc McStuffins? Behold the long, strange musical journey of a Red Sox fan. POSTED September 25, 2013

kayhThis is my new favorite Quaz.

I know … I know—those six words have been written here before. And before that. And before that, too. This time, however, I mean it. I really do.

What I love about the Quaz (as an entity) is the random beauty of the interviews. It’s exactly what I aspired to more than two years ago—unique, unpredictable Q&As with riveting folks from all walks of life. I’d ask the questions I want to ask, the way I aspire to ask them. No nonsense, no BS, no corporate sponsors. Just … talk.

Kan Hanley, former lead singer of the awesome (and terribly underrated) Letters to Cleo, is a talker. We spent roughly an hour on the phone, and her thoughts on everything from ’90s music to cocaine addiction to growing up alongside Marky Mark and a New Kid to backing up Miley Cyrus to the near-destruction of her life were riveting, fascinating, breathtaking. She is painfully honest and refreshingly quick-witted and as big a motherfucking fucking fuck fuck curser as I am. Oh, and she’s one helluva singer—as well as (alongside Michelle Lewis) the co-musical director for the cartoon, Doc McStuffins.

One can follow Kay on Twitter here.

Kay Hanley, welcome to the Quaz …

JEFF PEARLMAN: You were born in 1968, I was born in 1972. Hence, we’re about the same age. I’m increasingly feeling obsolete; as if my time has sorta passed. There’s a fight to stay relevant and get work. And sometimes I feel like it’s slipping away from me. You’re in the music biz—a biz that’s very fickle on age, appearance, etc. Do you ever feel this way?

KAY HANLEY: Absolutely. And I can answer your question very easily by telling you I felt obsolete when I was 22. I didn’t feel like being a singer in a rock band was a valuable thing to do. I thought I’d do something more substantial with my life. And I kept being led down this road. I never totally enjoyed it. And it kind of breaks my heart. Because when great things were happening for us in 1995 and ’96 and I could have been a rock star and … I just didn’t want it. It felt embarrassing to me. And yet I have this thing I did, which was to write songs and sing them, and it didn’t make me happy. It wasn’t until I went behind the scenes in music and, without even meaning to, redefined myself, that I found happiness in what I do. So yes, I totally get it. The feeling of, like, having to compete against the newest, greatest thing. I’ve had that experience. But I was already miserable.

Photo by Boston Globe.

Photo by Boston Globe.

J.P.: Why were you miserable?

K.H.: I just … it felt … I think being the singer in the rock band … being from Dorchester, being from where I’m from, it felt like really showoff. Like, ‘What, you’re too fucking big from your britches now?’ Like that kind of thing. Like calling attention to myself in this ostentatious way felt embarrassing. So I couldn’t really own it. I couldn’t own being a pop star. I just couldn’t do the stuff you had to do. So I felt irrelevant before we even got famous.

J.P.: That’s weird.

K.H.: It’s very weird. It’s a very Boston thing. Classic Boston psychology of deferring your happiness. But in this case, it was true. I really wasn’t going to be happy until I figured out a way to make being a songwriter and a singer work for me. So when I started doing, like, Josie and the Pussycats, or when Letters to Cleo composed the music for a show called Molly-O!, which was a cartoon about an 8-year-old rock star. And it was like, ‘Oh, this is what I like!’ And doing Josie and the Pussycats—I was just being paid for my voice. And, like, I didn’t have to do any press for it, I didn’t have to promote myself, I didn’t have to show off. I just had to show up and do my job, and I was good at it and I got paid for it. I thought, ‘This is where it’s at.’ I’ve been incredibly lucky since then that I’ve … I have ADD, so I can’t focus long enough to work on one project. So I’m constantly moving around. And luckily I’ve partnered with people who help me figure out the crazy ideas I want to pull off. And that’s how I keep it fresh.

J.P.: So you’re the baseball player who had his best statistical season at age 25, but you’re happier being 20 years removed from it?

K.H.: You know who I am? I’m Lou Merloni.

J.P.: You were a better player than Lou Merloni. Maybe you’re Jerry Remy

K.H.: Um, no. I’m really happy, and I feel Jerry has struggled to be Jerry. I’m maybe Dennis Eckersley. I wasn’t as good a player, but he’s hit his stride after his athletic heyday.

J.P.: I’m still confused. You’re in a hot band, you’re touring, you’re popular, you have a record deal. And you were unhappy?

K.H.: Ask anyone. It was very frustrating. I was a pain in the ass. I was a classic lead singer. I was very conflicted. Very conflicted. And I sabotaged things many, many times.

J.P.: What was your lowest moment?

K.H.: Oh, boy. Probably, I wrote a song about it actually called Galapagos. We were driving cross country from maybe the very last big Letters to Cleo tour. We were driving back from Seattle and we drove cross country on our tour bus, and I was just, like, really … I was doing a lot of coke back then and drinking a lot and feeling not great about myself. Even though I was conflicted about being hugely popular, I was even more conflicted about the crowds waning. The crowds getting smaller. That was really hard, too. I just remember driving cross country and feeling, “Oh, my God, I have to go home. And what are we gonna do? What am I gonna do with my life? I’m stuck in this thing and …” Of course my overdoing it on the substances back then probably didn’t help.

Screen Shot 2013-09-24 at 9.20.55 PMJ.P.: Don’t you think there’s this idea that you’re supposed to be happy. I see it with ballplayers. “You’ve made the Major Leagues! You’re in the clubhouse! Why aren’t you happy?” There’s this concept—Happiness. And you’re supposed to be happy, because you’re on tour. And it almost makes it worse because you’re not happy. No?

K.H.: That makes total sense to me. And I do see it in ballplayers, and you see how they sabotage themselves. They go and act the fool in public. They used drugs, they get in fights with women, they have a lot of material things and a lot of attention and a lot of these things you’re supposed to want, but they can’t live up to it. So you start acting a fool. And sabotaging it. And daring your fortunes to go away.

J.P.: How do you explain the pull of cocaine?

K.H.: You want happiness, and then you can’t stop doing it.

J.P.: Why, if it’s not providing happiness, can’t a person stop?

K.H.: I’m sober now, and have been sober for a number of years. And so I lived many years as an active alcoholic and addict. And I can tell you when you first start doing drugs, booze, whatever—for those of us who are addicts, it worked really, really well. It’s your medicine. But when it stops working … there’s a term in heroine addiction, “Chasing the dragon.” And basically it’s chasing that thing you feel the first time you do it. Or even the first line of the evening. The first bump of coke and that first drink—it’s like the perfect buzz. And you spend the rest of the night chasing that feeling to get it back. And it just gets worse and worse and worse and worse, and you never get it back, but you think that you might. And the next thing you know the sun’s coming up and you want to kill yourself.

I haven’t done coke in a very long time. But that’s a very, very dangerous drug, because it just sucks you in. It makes you feel so good, you just want to do it all the time.

J.P.: How did you go clean?

K.H.: Well, I burned my life to the ground three years ago. You know, I lost my marriage [Jeff’s note: Kay was married to Michael Einstein, Letters to Cleo’s guitarist], lost my children, almost lost my career. Uh, lost my friends. Lost everything. I hit bottom and I was literally dying. And I was given some opportunities to get help. And I finally was able to get sober on June 24, 2011.

J.P.: So is it like, “Hey, I’m happy now! Everything’s easy!” Or is life a struggle?

K.H.: I have worked very, very hard to get my life back on track. Yes, I’m a very happy person with a very big, beautiful life again. But I work at it every day. I won’t say it’s hard. I enjoy the work I do to stay sober. And everything in my life supports that. I’m pretty happy, and I don’t take it for granted. Two and a half years ago my family and my children and people who loved me really unsure that I would live through my situation. I do not take it for granted.

J.P.: I’ll turn to a somewhat happier subject. I know you’re from Massachusetts, I know Letters to Cleo, blah, blah. But how did this happen to you? How’d you get into music? What’s your life journey?

K.H.: Well, my parents had lots of records in the house, and my sister and I took piano lessons. I was terrible at piano. That’s a whole other story. I wasn’t gifted, but I could carry a tune, and I remember really enjoying singing when I was a kid. I would sing at mass with my mom, and through my early teens I had big hair and I was a cheerleader and I wore pink lipstick and blue eyeliner and listened to disco. And my sister Patricia brought home a Smith’s record when I was 17. And I heard How Soon is Now, and it changed my life.

J.P.: How so?

K.H.: I just couldn’t believe it. I heard How Soon is Now and I was like, “What the fuck?” I just couldn’t believe music could sound like that and that a band could make me feel like that. And I started dressing in black, and within a year I was in a band with my cousin Greg. I was 18 when Greg and I started our first band.

J.P.: Did you go from being the cheerleader to the weird chick?

K.H.: Instantly. And I had a boyfriend, and my boyfriend lived in the Southie projects and all of a sudden I’m dressing in black and he’s like, “What the fuck?” And I didn’t know anybody who wanted to be like that. I don’t even know how I knew dressing in black was a thing. But I knew. And I just wanted to know people who were into the Smiths. I wanted to know people in bands and stuff. Greg McKenna—who I ultimately started Letters to Cleo with—he was starting a band, and he asked me to be the backup singer in the band. We were called Rebecca Lula. And so Greg wrote all the lyrics and all the music and the bass player was the lead singer and I was the backup singer. And then one day, a few years into the band, Greg and I showed up for rehearsal early. And he had started this song, and he had lyrics written down. And he just started playing this chord progression. And I had the lyrics sheet in my hand. And as he’s playing the chord progression I started hearing this melody to go with the lyrics. And I just started singing this melody with these lyrics he handed me over what he was playing. We’re looking at each other and I’m like, “Oh, my God. Oh, my God.” And he’s like, “Oh, my God. Oh, my God.” We ended up writing this song together. I didn’t even know you could do that. I didn’t know how to write a song. That’s how it started. We wrote our first song together, and within a year we got rid of the band and started Letters to Cleo.

J.P.: Wait! What was the song?

K.H.: It was a song called “Me.” I asked Greg if he had a copy of it laying around not long ago. And he never sent it to me. We recorded it. The melody is awesome. I still remember it. And one recording we did of it we had a big sax solo. It was terrible. We had a problem with the quality of our taste level back then. But we figured it out. Eventually.

Screen Shot 2013-09-24 at 9.21.55 PMJ.P.: I’m gonna be lazy and throw something to you from Wikipedia. You grew up diagonally across from the Wahlbergs? Is that true?

K.H.: Yup, I did.

J.P.: I don’t even know what to ask here. Were you buddies?

K.H.: We hung out every single day. Donnie was my best friend. It’s funny—Mark is only two years younger than me, but back then it seemed like he was a little kid. So he was the baby of the group. And when we were younger and the boys started the first incarnation of New Kids on the Block … they were called Nynuk. Don’t ask me why. And the guy who started all those bands … Maurice Starr. He would have these big showcases for all his new acts at this school on the Dorchester-Roxbury line, called the Lee School. Which was an elementary school. So we’d all pile in the back of my dad’s station wagon and we’d all go watch Donnie’s crappy band play at one of these showcases. It was really funny.

J.P.: So was it weird to you when the New Kids on the Block blew up?

K.H.: Oh, so weird. So weird. And it’s funny. Because I didn’t see Donnie for a really long time. And a couple of years ago when I was singing backup for Miley Cyrus, we were rehearsing next to New Kids on the Block. And Donnie and I ran into each other in the parking lot of this big rehearsal complex. And we were just, “Oh, my God!” So every day at rehearsal he and I would meet at lunch and just go hang out in the parking lot and catch up and stuff. One of the big topics was, “Can you believe we made it out of Dorchester doing this?” We both agreed that was very unlikely.

We lived two houses down, across the street. And right next to my house was a light pole. My house was Alicia Road, and their house was Mercier Avenue.

Kay with her daughter Zoe.

Kay with her daughter Zoe.

J.P.: I fucking love the Josie and the Pussycats soundtrack, which is a really weird thing for a 41-year-old man to say.

K.H.: No it’s not.

J.P.: Yes it is. It’s kinda weird.

K.H.: No, it’s a great record.

J.P.: Do you ever get 41-year-old guys saying, “Josie and the Pussycats! Great soundtrack!”

K.H.: In fact, the first glowing article I ever got was in the Village Voice by this rock critic, writing about Josie and the Pussycats and writing about me in regards to it. [Jeff’s note: The critic, Mike Saunders, wrote that Josie was, “the best album you’re gonna hear all year.”] That was the first time I had ever gotten any major respect from what I considered to be a cool publication. I went on Howard Stern and he was in love with the Josie soundtrack.

J.P.: Because the film wasn’t much …

K.H.: Oh, it wasn’t. It didn’t do very well. It was kind of ahead of it’s time.

J.P.: How did you even end up as the voice of Josie?

K.H.: Well, my friend Dave Gibbs, who was in a band called the Gigolo Aunts. He had moved out to LA a couple of years before, and he was paling around with people looking for musicians to do music for their movies. And he hooked up with people doing Josie. Babyface was producing the music for the movie, and Dave somehow got hooked into curating the music that would go into the movie. At the time there was no soundtrack. So he was curating songs for the movie, and Babyface had already hired a singer to do Josie. So Dave was like, “You should get my friend Kay to come out here and do the voice of the Pussycats.” My ex, Michael, myself and my 11-month old daughter, Zoe, we hopped on an airplane and moved into a hotel in West Hollywood. By the time we got here they had let this singer go. Babyface is from the R&B world, and he hired a girl to do Josie. She was this black woman with this incredible voice. Because it was raspy, he thought it sounded like a rock and roll voice. But as soon as they looked at Rachel Leigh Cook and heard this voice they said, “There’s no way this voice is coming out of her mouth.” So it allowed me to kind of swoop in and take the job. And that’s what happened.

Screen Shot 2013-09-24 at 9.23.08 PMJ.P.: I ask this with 100-percent respect. In 2010 there was an award show, and Stevie Nicks sang backup for Taylor Swift. And I was sorta like, “Are you kidding me? How is this possible?” So I learn you sang backup to Miley Cyrus—and my first thought was, “Are you kidding me? Kay Hanley’s voice is so much better …” Is this a dumb way of thinking?

K.H.: Yes. I’ll tell you why. First, I did take a lot of shit for it. But by that time I really could not have cared less. There was a period of time where I did care what other people thought. But by then I had become a businesswoman. And I had this whole career as a producer and a publisher and an artist developer and a manager. I had a thriving business. And I was doing quite well in my professional career. By then I was completely impervious to what anyone had to say about what I was doing. And Stacy Jones, the drummer from Cleo—he got the job as her music director. And he was just like, “Hey, Kay, would you be interested in doing backup for Miley?” Actually, before that he was auditioning people to be her band. There were two days of auditions, and she couldn’t be there. So he hired me to come in and just sing Miley songs over and over and over again while they auditioned people in the band.

Kay, right, backing up Miley Cyrus in 2008.

Kay, right, backing up Miley Cyrus in 2008.

J.P.: Was that fun?

K.H.: It was so much fun. Like I said, I just like doing something different all the time. I got to spend all day singing these pop, super-fun-to-sing songs. Totally in my range. It was so much fun. So they put together the band and they were planning the tour. By then her management knew me, and they knew I could sing her songs like her. So Stacy asked if I wanted to come on the road and sing backup. I asked Michael if he’d take care of the kids while I went on the road. The money was great. I took it. I’m 38 years old, and I’m learning choreography, going out and playing these huge arenas. I’ve never done that in my life. It was the funnest thing. And it was like going to the gym, so my body was slamming. I was in amazing shape. Oh, my God, it was the funnest job I ever had to this day. And not for nothing, but Miley Cyrus can sing her ass off.

J.P.: It sounds like a good-money, zero-pressure gig?

K.H.: Sparkly outfits and I’m dancing on stage! And I love dancing, so for me to learn how to actually dance … it was so much fun.

J.P.: So the talk of the world for a while was Miley and the VMAs and shock and blah, blah. What was your take of it all?

K.H.: I thought she was a 19-year-old girl trying to act like a sassy big girl. I mean, she was doing what rock stars should do, which is act out and call attention to yourself. She was doing the thing that I never could do. And the idea of the VMAs is that somebody is going to win the prize for being the most outrageous person. She went for it and she won the contest. And good for her.

And now she’s got her first No. 1 hit.

J.P.: Don’t you think it’s interesting how people become old so quickly. The same people who loved David Lee Roth shoving a mic stand between his legs are so outraged. People grow old quickly …

K.H.: That also makes me insane. I mean, personally I thought it was so contrived and so tame compared to how people used to be every day. For  example, and this is tangential, when we made the video for Here and Now, I rolled out of bed that morning, probably late, I don’t think I took a shower. I dug some clothes out of a corner of my room. Maybe my clothes were clean and folded. Probably not. And I put my dirty hair up in ponytails, because that’s what I could do with my hair that day because I’d just rolled out of bed, and then we went ahead and shot a video. And then it ended up being a big video for us.

And now, rock bands—you wouldn’t go to a video without having a team of stylists. Boys having hairdressers and makeup on the set of your video. Music has gotten so safe and so contained and so … the musicians have embraced the idea that it’s the music business. When we were young, musicians couldn’t run away fast enough from the idea that it was a business. And, I don’t know that there’s anything wrong with that necessarily. In today’s day and age, when records aren’t selling, you have to figure out a way to get your image out there. But there’s just this incredible lack of risk taking. So when Miley goes and does this weird, contrived thing of sticking her tongue out. I mean, I thought it was silly, to be honest. But it doesn’t make me mad. At least she was doing something. And she opened herself to be criticized.

The anger was so self-righteous and so ridiculous.

Screen Shot 2013-09-24 at 9.20.13 PMJ.P.: You’re supposed to be this hard-core Massachusetts gal … and you’re living in Los Angeles? What the hell?

K.H.: It’s where the work is, baby.

J.P.: Are you going to Dodger games and wearing a Puig T-shirt?

K.H.: C’mon. When the Red Sox came to town I did take my son to watch at Dodger Stadium. And I do like the Dodgers. They’re National League. I let my son wear a Dodgers cap. Mind you, I wouldn’t let him wear an Angels cap for a lot of reasons. But I feel like it’s the National League, the team is very exciting this year and it’s fun to check them out. But am I fan of anyone but the Red Sox? No.

J.P.: Do you like living in LA?

K.H.: I’ve never felt like this is home. This is where I am to work. I’ve had a great career out here, and my career is better now than it’s ever been. So for that reason I like it. But the goal for me is to become successful enough that I can move back to Boston and my phone still rings. But if I’m not here, my work goes elsewhere.

J.P.: What’s your main career focus?

K.H.: All Doc McStuffins, all the time. We’re about to go on hiatus, so I might do some pop writing. Being a composer for Doc McStuffins is great. It’s the biggest job I’ve ever had. A lot of responsibility, a lot of work—and it’s all consuming. When we’re in production there’s nothing else I can squeeze in there. As a musician, I’m the luckiest motherfucker ever—because I’ll be employed for the next five years. I’m so lucky. The difference between now and 1995 is now I enjoy every second of what I do. I’m so present, I’m not thinking about what better thing I can be doing. I love my job.

Screen Shot 2013-09-24 at 9.17.28 PMQUAZ EXPRESS WITH KAY HANLEY:

• Why the name Letters to Cleo?: My pen-pal growing up was named Cleo. She lived in Canada. My grandfather owned a motel in Nova Scotia. So every summer the family would get in the car and drive to Nova Scotia, and I would spend every day of the summer playing with Cleo. And then we would write to each other all winter long. So that’s why we named the band Letters to Cleo. It was just kind of a temporary name that stuck. This summer we were on the Cape at my parents’ house, and the kids were going through all these photographs in my parents’ basement. And they came across this school picture, and on the back it said, TO CATHY, FROM CLEO, AGE 11, 1977. And they were like, ‘Holy crap!’ I have a chill right now telling you this. It’s so intense, because I almost forgot that she was real. And she changed my life. I will forever be associated with this person I haven’t seen or talked to since I was 13. I’ll e-mail you her photo …

CleoIn 2006-07, you sang the National Anthem for eight-straight Patriots wins. How do you explain that?: Just lucky, man. And then I blew it on the last one and they never asked me back. I knew it would happen, because they called, like, two weeks before the game—a playoff game. Welker had gone down two weeks before and they called and it was the first playoff game and I said, ‘Oh, my God, yes!’ And I hung up and thought, ‘Oh my God, they’re gonna lose.’ Also, it was Hot Stove Cool Music the night before, and I got wasted. I was wasted, and the car came to pick me up the next morning. I was not in good shape. I remember Tweeting from the car service to Foxboro, “This hangover is not very patriotic.” And, of course, I sang terrible, and then they lost. It was terrible. And the Globe took my Tweets and blamed me for the loss. Which I was kind of oddly proud of. So I blew it and they never asked me back.

• Five favorite Red Sox of all time?: Freddie Lynn, Carl Yastrzemski, Dustin Pedroia, Jacoby Ellsbury, Jim Rice.

Rank in order (favorite to least)—Celine Dion, Luis Tiant, Rex Ryan, Jeff Horrigan, Starbucks’ new pastries, Joe Flacco, Run DMC, Legoland, Twitter, Bobby Valentine, Tesla: Jeff Horrigan, Twitter (Twitter is my life. I’m a Twitter whore), Run DMC, Luis Tiant, Starbucks’ new pastries, Celine Dion, Tesla, Rex Ryan, Legoland, Joe Flacco, Bobby Valentine.

• Rank in order, Rock n Roll Hall of Fame worthiness—Hall and Oates, Kiss, Styx, Chicago, REO Speedwagon, Blind Melon: Are none of these guys in the Hall? Wow. Hall and Oates first, for sure. Then Chicago for sure, next. REO Speedwagon. Kiss, Styx, Blind Melon.

• Five greatest vocalists of your lifetime?: God, of my lifetime? Shit. Oh, God. Jesus, this is hard. I’m gonna go with, not greatest vocalists, but vocalists who influenced me. Michael Stipe, Bjork, Jeff Tweedy, Morrissey. I only get one more, huh? Prince.

• Why do you think people are so attracted to musicians even if they’re physically ugly?: Anyone on stage is sexy. I don’t know why, but I feel that way. I don’t know why that is. But I’ve always been so attracted, even to this day, I just love people in bands.

• So you see Lyle Lovett on stage, you think, “Ahhh, Lyle …”: Well, I wouldn’t want to fuck him. But I’d want to know him. Is that gross? Is that TMI?

• Fear of death—scale of 1 to 10?: Um, two. Well, I know what it’s like to almost be dead. I did almost die many times. And, also, if I went out now, I’d go out at the top of my game. I would just hate for my kids not to have their mom.

• Have you ever thought you were about to die in a plane crash?: I had a deep fear of flying for about 1 ½ years back in the 1990s. It wasn’t a specific fear—but my heart would just pound for days before I got on a plane. Then I got hypnotized, and it worked. In fact it worked bizarrely well. My label made me go to the hypnosis in 1997, and I was afraid of going on this promo tour. I was going to have to fly all over. I was flipping out. We were getting on a plane from LA to Boston, and the label insisted I go to a hypnotist. I got on that plane that day and it was fine. After that I’d go to Castle Island in Southie every chance I got and watched planes take off and land. It was the weirdest thing. And I’ve never been afraid since.

• My good friend is dating a complete jerk. What should I do about this?: Nothing. Unless he’s hurting her. You risk—here’s the thing. In this life people really appreciate arriving at their own conclusions and finding their own answers for themselves. You run the risk being resented by your friend if you intervene.

• I was hoping you’d tell me to kick his ass: Nope, you do nothing. Just love and support her and show her what a man of honor is.

Showtime Book
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Once again, Jeff Pearlman has produced an exhaustively researched, elegantly written book that re-creates one of the most colorful and memorable teams of the modern era. No basketball fan's bookshelf will be complete without it.

— Seth Davis, author of Wooden: A Coach's Life