Molly Ringwald is set to hit the stage in the musical Sweet Charity Sept. 12-17 at the San Diego Civic Theatre as Charity Hope Valentine, the taxi dancer with a heart of gold, following in the footsteps of Gwen Verdon and Shirley MacLaine.

Ringwald has been surrounded by music her entire life. Born to blind jazz pianist Robert Scott Ringwald, the youngest Ringwald daughter would frequently make appearances with her father’s jazz band.

At 6 years old, she released an album entitled I Wanna Be Loved by You, Molly Sings. She also scored gigs on “The New Mickey Mouse Club” at 8 and the West Coast production of Annie at 10.

In1982, she made a name for herself on the silver screen in the film Tempest, starring alongside Gena Rowlands and Susan Sarandon.

But her ascent up the ladder of teen stardom began when she was teamed with director John Hughes in 1984’s Sixteen Candles.

While most teenagers her age were worried about breaking out, Ringwald was breaking out as an actress who brought an air of realism to her roles as the outcast and the ostracized – something that many gay teenagers could relate to.

In 1985’s The Breakfast Club, she starred as Claire Standish, the popular antithesis of her Samantha Baker character in Sixteen Candles.

In 1986, her teen-queen trifecta was completed with her portrayal in Pretty in Pink of Andie Walsh, a girl on the wrong side of the popularity tracks. That same year, she was featured on the cover of Time magazine with the headline “Ain’t she sweet.”

Ringwald ventured outside of the Hughes bubble in the teen pregnancy flick For Keeps before securing adult roles in The Pick-Up Artist, Fresh Horses, Betsy’s Wedding and the TV movie Something to Live for: The Alison Gertz Story, the true story of a woman battling AIDS.

In the ’90s, she spent time living in Paris and appeared in the television show “Townies” and the mini-series “Stephen King’s The Stand.” She also married Valery Lameignère, though the two are now divorced.

The new millennium saw Ringwald spoof her teen-queen image in Not Another Teen Movie. She did the film because the filmmakers “offered me a ridiculous amount of money,” she said. The film also showed she had a sense of humor about her place in the pantheon of teen roles and that she had grown beyond them.

Ringwald then returned to the stage in Modern Orthodox, Enchanted April, Cabaret and When Harry Met Sally. But her biggest role took place offstage, when she gave birth to her daughter, Mathilda, in 2003 with boyfriend Panio Gianopoulos.

Ringwald spoke with the Gay & Lesbian Times in between rehearsals for Sweet Charity.

Gay & Lesbian Times: What was it like having your teenage years documented on film?

Molly Ringwald: At the time, it didn’t really seem all that significant; it was just what I was doing. I didn’t know that those were my awkward years until after [laughs]. Actually, you know what? I don’t think that my teen years were all that awkward; I think it was my early 20s [that] were kind of awkward.

I think it seems kind of strange in retrospect, ’cause not that many people have their first kiss documented on film. And it’s kind of like a double-edged thing; I think it’s kind of neat in one way, and in another way it’s sort of perverse. But there it is.

GLT: How did it feel to be voted the No. 1 teen star of all time on VH-1’s “100 Greatest Teen Stars”?

MR: Well, as my mom said, it’s better than being No. 2 [laughs].

GLT: Of the characters you played in the John Hughes films, who were you most like and why?

MR: At the time, I was probably most like Samantha. I was kind of at the age where I felt like an ugly duckling, definitely. I was sort of like the character in Pretty in Pink as well. Because of what I did, I was sort of different than everybody else at school. So I kind of got ostracized for that, much in the same way that she’s ostracized for being from the so-called wrong side of the tracks and not having the right clothes to wear and everything.

I really wasn’t at all like the character in The Breakfast Club. I put elements of my sister, who was a popular sorority girl, and she was in this sorority called The Puffs, and I kind of knew about the popular girls from that.

GLT: Which theater role was the most challenging?

MR: I think that the theater role that’s most challenging is the one that I’m doing right now. Maybe I just say that because I’m in rehearsals right now and I’m learning all these dance numbers and thinking: “Holy shit! Can I do this?” [Laughs]

For me, I always like to do things that scare me a little bit. And definitely dancing is something that I gave up on really early, when I got sidetracked by my film career. So this is something that I’m revisiting in a really intense way.

But then all the theater roles I’ve done have been challenging in one way or another. Cabaret was incredibly emotionally challenging, and physically too. There was a lot of running around. All theater is pretty much a grind, much more so than film. Film is like you wait around and then go and do your shot. It’s such a cakewalk compared to theater.

I’ve always liked the feeling of doing live theater. It’s the closest you can get to a regular job, I think, in our business.

GLT: How do you balance motherhood and doing a national tour like Sweet Charity?

MR: I’m actually realizing that this is the first time that I’m taking on such a big role and being a mom. My first play that I did after she was born, she was eight or nine months, was When Harry Met Sally in the West End. And that was fun because we got to go over to London, and she got to be a little baby in the London parks.

Then I came back and I did Modern Orthodox, and I feel like I really didn’t find a good balance then. I felt like I was spending way too much time just totally devoting myself to that.

So this time I’m trying to go home and spend a couple of hours where I’m not listening to the music, and I’m not practicing dance steps or running lines. I’m just running around with her and doing kid stuff. I have to, for her and also for me, because that bond is really important to me.

GLT: What can audiences expect from your rendition of Sweet Charity?

MR: I’m still finding that out now. Hopefully, they’ll be [able] to relate to this character. I don’t want her to be caricatural at all.

A lot of people, I think, are turned off by musical theater because it’s this kind of acting where everything is, like, out. All of the talking is just sort of something that fills in between the dance numbers.

My Charity is not like that at all. I think that the book and the script and this woman should be every bit as important as the dance numbers and the singing numbers. So I’d like to bring that to it.

Hopefully, they can expect to see something really exciting and fun – and a great head of red hair!

Tickets are $19 to $75. For ticket information and showtimes, call (619) 564-3000 or log on to www.broadwaysd.com. The Civic Theatre is located at Third and B streets downtown.