At 28, Kelly Cutrone Read Tarot On Venice Beach & Signed A Record Deal

For a certain subset of MTV-loving millennials, Kelly Cutrone needs no introduction. The public relations maven was a standout on The Hills and its spin-off The City in the late aughts for her all-black wardrobe and no-nonsense attitude. As the founder of the fashion PR company People's Revolution, where the show’s stars Lauren Conrad and Whitney Port served as interns, Cutrone was equal parts their foil and their mentor. “I was very polarizing on television. But that was the first time [young viewers] got to see inside a fashion office, and certainly inside a publicity office,” Cutrone, who also starred on Bravo’s Kell On Earth, tells Bustle. “That caused a lot of young girls and gay kids to go into PR because they watched that show. I felt like I really gave them permission.”

By the time Cutrone, now 57, entered her reality TV era, she was already a bonafide boss. But in her twenties, she busy making a name for herself. She worked with famed publicist Susan Blond, held a job at SPIN magazine, then worked with clients like Mark Ronson and Eartha Kitt at her own talent agency. But after a series of setbacks in her personal life, Cutrone decided to take a step back from the PR world. “[In my early 20s] I was kind of an ‘it girl’ in New York. I was one of the hot, young, successful girls at the time,” Cutrone says. “But on the inside, my life was falling apart and my marriage fell apart. So I split and I moved to LA.”

As Cutrone puts it, at 28, she was “very, very, very wild.” She lived in a hotel above Swingers diner, got heavily into drugs, then detoxed and started reading tarot cards on Venice Beach. But after landing a surprise record deal (more on that later), Cutrone began her journey back to PR. “I do think that I overshot it. I'm a little extreme,” she says of her legacy. “But at the same time, I'm proud of myself for sticking up for women, and I'm proud of myself for telling the truth as much as I do.”

Below, Cutrone talks being given a $6,000 cashmere coat, her spiritual practice, and making out with Jane Fonda.

Take me back to 1993, when you were 28.

I was just doing a ton of drugs by this point. I was drinking, doing coke. I was a hot mess. Then, right around the time that you're asking me about, I had this major spiritual experience. It was a whole thing — physically and emotionally. I went through a horrible detox and that was the last time I ever did any drugs. And I've never missed a day without doing spiritual practice since then. I also started reading tarot cards on Venice Beach.

How were you feeling about your life and career?

I was living the LA Dream. I started getting [tarot] business, like regulars coming back. [One day I was] sitting there reading tarot, and these guys show up I knew from New York. This guy named Sean Dinsmore from [the ska band] The Toasters. He goes, “What the f*ck is up with you, man? You're so different." So he calls me later and goes, "Hey, [my new band and I] are going to be in the studio. Do you think you could come by? I want to play something for you." So I go to the studio and he plays this beat. Then he was like, "We were thinking maybe you could just kind of talk-sing and we’d record you." I was like, "Okay. Am I getting paid for this?" Then I did it and it became a song called “Conversations with a Groovy Girl.”

Sean called me later and goes, “Atlantic Records heard the record. They want to sign you.” I said, "I don't know how to sing. What are you talking about?" He goes, “You’re going to get a record deal.”

Were you so excited? Or were you like, what did I just get myself into?

Upstairs from me [in my apartment building] was a girl named Chantal who was a player. So I went home and she's like, "How's your day?" I said, "I think I'm getting a record deal." She goes, "What? You need to meet Richard Perry.” Richard Perry produced “You're So Vain” for Carly Simon and Chantal was dating his best friend. So I go into the studio with Richard and we make a demo and we [start planning] to go to New York. I'm so poor that I don't even have a winter coat. My whole wardrobe was two pairs of jeans, two tank tops, a leather jacket, and a hoodie. That's all I had. I go, “Richard, I don't even have a coat." He took me to Fred Segal and bought a full-length, cashmere, really beautiful $6,000 coat. He goes, "You're going to look great." Then we went [to New York] and I got signed to Atlantic Records.

Once you got the record deal, did you splurge on anything with your own money?

I went to the bank, which was really funny because I didn't have a bank account. I tried to cash a check for $250,000. That's how much I got signed for, some big ass cash. Richard got 50% of it, but Richard’s great. He ended up dating Jane Fonda at the end of his life and Jane threw the Kell on Earth premiere. I actually made out with Jane Fonda.

What?!

I was at dinner with Richard Perry, Jane Fonda, Al Pacino and his girlfriend Lucinda, who’s Camila [Morrone’s] mom, Robbie Robertson and I think Robbie's wife, and [producer] Nick Reed who’s Harris Reed's dad. So we're at this dinner and all of a sudden my record comes on and Jane jumps around, over the table, and somehow ends up on my lap, and we kissed. Jane Fonda's hot. I'm here to tell you.

After the deal, did you keep pursuing music?

While my record was going on, I was also doing PR. The beginning of People's Revolution started right around that time, too. It was really a very vibrant and tumultuous time in my life.

Do you have any regrets from being 28?

I participated in behaviors that were degrading and horrifying to me and others, but that's what it took for me to get real. Would I want my daughter to behave like that? Absof*ckinglutely not. But not to be rude to my family, I wouldn't have left my daughter in that situation for that long. My mom went to Al-Anon and read a book about tough love. So I would call them in the middle of the night, tell them that I was going to be dead, that I was going to OD, and it was going to be their fault. Nobody wants to hear that and I had to take responsibility for that part. But do I regret that? Shaking my mom down a couple times? Yes, I do regret shaking my mom down. But that's what it took.

Has there been a moment in your life or career where you felt like you’ve made it?

No, but I feel like I mowed a nice lawn. I was the first poor girl in PR. Everybody in my world was super rich. I came from the middle of nowhere, my sister and I shared a bed, if we were going to get school clothes my parents had to sell things. I was really embarrassed about where I was from when I came to New York. Then as I got older, in my early thirties, I started feeling like it was something I should be proud of. Still to this day, I get so many emails and DMs from people like, "I saw you on that show and I moved to Toronto and now I own ten hair salons. I just faked it until I made it." It's super cool.

You’ve also mentored, or employed, so many people who have gone on to have massive careers after working with you. That’s certainly part of your legacy.

A lot of f*cking kids. Harris [Reed], I definitely raised. He used to come and stay with me in New York City at my house and work for me at People's Revolution during the summer so he wouldn’t be bullied [at home]. I also put him in fashion classes and stuff while he was growing up. I did Rag & Bone with [co-founder] Nathan Bogle from day one. Tracy Romulus [Chief Brand Officer of KKW Brands] was a shop girl at Vivienne Westwood and I would go there a lot because I was [Vivienne’s] publicist. One day I started talking to Tracy and I was like, “I need an assistant. Why don't you just come and work with me?" She became my assistant at People’s in New York. I mean there’s a ton of them, I still mentor even now.

What would your 28-year-old self think of your life now?

The first half of my life, I [did] what everybody wanted me to do, which was, "Be your best, be pretty, smart, polite." I spent so much time being “that girl.” But when I was growing up, it came a time where you had to make a decision. Do you want to be this guy's wife or do you want to own People's Revolution? So I [became] a solo wolf.

This interview has been edited and condensed for clarity.