At 28, Bridget Moynahan landed a television role she would reprise two decades later

Bridget Moynahan still remembers speeding down the Sunset Strip and listening to Prince's album "1999" as she drove to the set of her 2000 hit "Coyote Ugly." played repeatedly, hair fluttering in the wind. She spent hours learning how to swing a bottle behind her back to accurately portray Rachel, a shit-free bartender who works at the Coyote Ugly Bar, and her hands were getting tired. When the film premiered the following year, its billboard dominated prime real estate on the avenue. "That was the first time I realized, 'This is going to be a big movie,'" Moynahan tells Bustle.

Moynahan is 28 years old and has a lot of dreams coming true. She has built a modeling career, appearing regularly on the covers of Glamor and Cosmo . Although it was difficult to break into showbiz, her years of grueling auditions finally paid off: In addition to filming "Wolf Ugly," Moynahan also starred in "Sex and the City" as Mr. Big's ultra-stylish Ralph Lauren. Lauren's model girlfriend Natasha makes her TV debut . The character was so amazing that Carrie threw up immediately upon seeing her. Although the role was relatively small, it was so memorable that Natasha became a recurring character.

“She became Carrie Bradshaw’s silent nemesis,” Moynahan recalled. "Years later, when people would talk to me about Carrie, I'd be like wait a minute... Big cheated on Natasha and don't forget, you can't stand up for Carrie!"

Moynahan, 50, who has 20 years of experience and 12 seasons on the hit network series "Blue Bloods , " will return to her first TV job, starring in the HBO Max reboot of " Desire" Played Natasha in "The City" (And Just Like That) . It was a full circle moment. "I could never have predicted my career," she said. No one could have predicted that Carrie and Natasha would meet again after so many years.

Below, Moynahan discusses the energy on the Sex and the City set, her favorite leather pants, and the advice she'd give to her 28-year-old self.

Moynahan in "Wolf Ugly." Archive Photo/Moviepix/Getty Images

What was your life like as a 28-year-old in 1999?

This is actually very exciting. I just finished filming Sex and the City . I was living in Los Angeles filming Coyote Ugly and working with a trainer, learning to dance and drive in Hollywood. This is a new life for me.

What was your most memorable moment while filming Coyote Ugly ?

All of this is so exciting because it's such a complex process. The cast worked together, rehearsed together, learned dance together, learned how to wave bottles behind the bar - it was special. It’s not like every project where you immerse yourself in your actors from day one. This was my first big movie - I'd done a couple of independent movies and then Sex and the City , which was very big in its own way, but it wasn't like this. It's a wonderful introduction to the world of cinema.

I had been living in New York, going to acting school at night, filming with my scene partners on the weekends, and still modeling during the day to pay the bills. After focusing so hard and putting in the time to go to acting school, getting a project like Wolf Ugly is such a great reward. I really had no idea what I was getting myself into. I really had no idea who Jerry Bruckheimer was and I didn’t understand the magic and power he had. He just created such huge blockbusters - I don't understand how lucky I am to be involved in this. That year everything came together. This is a big year. Not to mention my favorite album is 1999 , so I listen to Prince all the time.

At 28, you also made your TV debut as Natasha in Sex and the City 's acclaimed drama "The Hamptons," where Carrie discovers Big met you in Paris and begins to unravel. Do you remember the feeling of arriving on set for the first time?

I had a very clear vision of what it would be like to set foot on Sex and the City . If you can imagine a full double Dutch game - a skipping game - and that rhythm and rhythm and then you have to jump in, that's what it's like. It's such an energy. I couldn't believe it, all these years later, walking onto the set of This Is It and it was still there. Whether you're in the hair and makeup trailer or in the crowd, it's huge, energetic, positive, and has an exciting feeling to it. This time I was really able to take it all in and say, "Wow, this is so special."

As a young actor who had never really done anything before— Sex and the City was before Coyote Ugly —I honestly didn’t even have any lines other than “Hi, nice to meet you.” But I still needed to make sure my lines were right, and I just didn't want to screw it up. You're just thrust into it. It’s a well-oiled machine and you have to jump right into action and I was really nervous.

People often confuse villains with the actors who play them. With so many people rooting for Carrie and Big, were you nervous to be on the show?

You know, I really felt like I was naive. I was like, I got a job. To be honest, I really wanted to get a job. I had no idea what Sex and the City was. I knew it was a show, but I had no idea what it meant to play this character. Maybe this is better, maybe ignorance is bliss. I didn’t think too much; I didn’t put too much pressure on myself other than not to mess up . Like at the end of the day, say your lines, don't mess up too much, and hope they get back to you.

Did you have Natasha in your life?

If there’s a real Natasha right now, it’s George Clooney’s wife, Amal Clooney. She is simply the epitome of perfection. Smart, versatile, compassionate, beautiful. To me, she is everything. She is the real Natasha.

Do you feel a sense of accomplishment at the age of 28? Do you feel like you know where you want to go in life?

I felt like at that particular time, I had already had a great modeling career, and Sex and the City and Wolf Ugly being my springboard in the industry was very exciting and very promising. I definitely feel like it's good, definitely, I'm on the right path. I'm making a living.

Do you have any other hobbies or passions?

I'm an amateur photographer. I had some old Polaroid cameras and I would walk around and take pictures with black and white images. I had a boyfriend who was a musician who lived in Los Angeles, and he bought me a guitar, so I was learning how to play it. I have to say, it's a pretty cool life.

Was it a difficult adjustment period moving from New York, your longtime home, to Los Angeles?

In New York, you know it's a grid - Los Angeles is not a grid. Driving on these highways, I would call my girlfriend, "I'm in La Cienega, I have to go to the 405...where do I go?" Thank god for Waze and Google Maps. I cried a lot on the road.

What was your style like at 28?

In fact, I wear a lot of leather low rise strappy crotch pants. There's a designer called Henry Duarte who's designed for a lot of rock stars, but I really like these pants. I really love them, I have a whole box of them that I can’t fit anymore. I was inspired by the Coyote Ugly wardrobe.

What advice would you give to your 28-year-old self?

Go buy property. Forget shoes, real estate would be a good idea. And trust my instincts. I remember a project that the writer-director wanted me to audition for, and I asked an actor friend to work with me, and he kept giving me notes, and I was like , seriously ? I just didn't see the notes. I auditioned but didn’t get it. I remember walking away thinking, I didn't do this my way . I didn’t use my intuition or trust my gut. I took that moment as a learning experience and trusted my instincts.

This interview has been edited and condensed for clarity.