An exclusive interview with pop sensation Tiffany

photo credit Emily Jones

All the great divas are known by only one name: Madonna, Cher, Beyonce and 80's teen sensation Tiffany! As a teenager herself, Tiffany set a record for the youngest female artist to top the Billboard album charts. For the past 34 years, she's been making music and performing in the Chicagoland area.


Her first stop in our area was in August of 1987 at Woodfield Mall, during her iconic promotional mall tour. Her last stop to our area was during the Mixtape Tour alongside New Kids on the Block, Debbie Gibson, and Salt-N-Pepa.

She returns to Chicago this Sunday for two intimate shows at City Winery on Father's Day. We had a chance to chat with Tiffany by phone to talk her new music, her favorite song she recorded (hint: it's not 'I Think We're Alone Now'  and country superstar Carrie Underwood covering her music on 'American Idol.'

The first time you came to Chicago was in 1987 during a promotional tour at Woodfield Mall. What do you remember about that time in your life.

The mall tour was really special to me. I love a mall because of it. I mean, it was the beginning of my career, the fond memories and not knowing what's next. Seeing the girls in jean jackets and making friends with the fans who came out. It was very special.


You're bringing your Shadows Tour to Chicago on Father's Day. What memories do you have of dads bringing their kids to your shows and now that they are adults coming to shows now.

It's amazing to see parents bring their children to the shows. It's been amazing to grow up with everyone. Like my girls who had the jean jackets and my guys who secretly had me on their wall, which is cool. My gay fans who were finding out about themselves and some of my songs connected with them. A lot of artists are setting dates in the fall, and to be one of the frontrunners now to be on the road, I'm thrilled to be doing these shows.

Did you think the legacy of "I Think We're Alone Now' would be this immense. You hear it all the time on the radio, at weddings, and a staple song of the 80's.

It feels amazing. I am forever grateful. Coming from Norwalk and wanting to sing and it all happening, and 30 years later I"m still going. This all happened because of 'I Think We're Alone Now.' The song makes people happy, I never get tired of singing it. I sing it everyday, even on Cameo, I'll sing it for each of the videos. I am forever grateful, because it's taken on its own life. It's a proud moment of mine to be a part of music history.  'I Think We're Alone Now' was also one of the biggest songs of 2020. It was a mix of messages I would get from fans. From people hanging out at home and blasting the song and sometimes people messaged me and we're like 'No girl, I'm really alone' 

During Season 4 of American Idol, Carrie Underwood covered 'Could've Been.' Did you see her performance. Have you met her?

I've seen it. She's amazing. I'm a fan. I've met  her a couple of times. She's lovely and she's always been wonderful to get to know. It's a beautiful song , 'Could've Been.'  You know, 'I Think We're Alone Now' is a lot of fun.  but 'Could've Been' is my favorite song I ever recorded. For so many reasons, they told me not to record it. So there's also a rebellious angle to it. They told me I was too young to record it, and I said not really.Because Have you ever seen a 14 year old girl 
in love, it's the end of the world. So those lyrics meant something to me. 

Let's talk "Hey Baby' and some of the new song you'll be playing on this tour

We do all the retro stuff. 'I Saw Him Standing There' 'Could've Been' 'I Think We're Alone Now' but for the people who have been there over the years for 'Pieces of Me' and 'A Million Miles'. we've got those songs too. This new album is rock retro - it's a celebration of 80's music. It's fun, easy, and energetic.  It's rock retro with a modern day flair.

The last time you were here was during the Mixtape Tour with New Kids on the Block, Debbie Gibson, and Salt-N-Pepa. What was it like to be a part of that tour.

It was amazing. It was great to have everybody together. It was a life-changing event for me. and to have the love and support from the other artists was amazing. The tour was magical and people lost their minds over it every night. I loved the meet and greets too on The Mixtape Tour and we will be doing that on this Shadows Tour too. 

Catch Tiffany this Sunday, June 20th at City Winery for a show at 5pm and 8pm 
Tickets are available at https://www.citywinery.com/chicago/Online/default.asp?BOparam::WScontent::loadArticle::permalink=CHI-Tiffany-6-20-21-8pm&BOparam::WScontent::loadArticle::context_id=
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