[January, 1989] Tiffany vs Debbie Gibson: The Ultimate Showdown

1/17/89

Dear Journal,

I went to Pennsilvania and it was fun. There was a boy my age there named Wallace who gave me a tape. Tiffany.

Tomorrow night I am going to sleep over Rose’s and stay at her house for Thursday and Friday. I am not really mad at Rose but we get along pretty well.

Today we are going on a trip to prospect park. I am going to be partners with Nisa and Jessica.

I am glad things are working out well for me.

Art by DoA

I still remember that cassette, covered with green and blue marker squiggles to the point where you could barely make out the song titles. That weekend, I played that Tiffany tape so many times, I think by the end of my stay Wallace was happy for me to take it off his hands. I wouldn’t be surprised if to this day he shudders every time he hears “I Think We’re Alone Now.”

There have been numerous pop culture debates over the years. Coke vs Pepsi. PC vs Mac. In terms of music there’s been The Beatles vs The Rolling Stones and Blur vs Oasis. In the late 1980s there was a media imposed rivalry among two teen pop sensations: Debbie Gibson vs Tiffany.

Back then, numerous teenybopper magazines had charts comparing the blonde from Long Island and the redhead who got her start singing in shopping malls. As if we had to choose. While I discovered Debbie Gibson first, I wore out my copy of Out of the Blue and was thrilled to find another singer in the same vein. Back then, my main source for discovering music was Casey’s Top 40, which could be tedious considering all the commercials, the hit songs I wasn’t crazy about, and all those request letters Casey Kasem read on the air. Being handed a tape that contained songs I instantly loved was like magic.

While I have a tendency to be pretty damn gullible, I saw the Debbie Gibson versus Tiffany debate for the marketing ploy that it was. Why did one have to be better than the other? Why did we have to choose between them? Yes, Gibson wrote her own songs and had more Top 10 hits, but Tiffany had a bit of an edgy rasp to her voice and wasn’t afraid to sing her guts out to make “Could’ve Been” the heart-wrenching ballad that it was. Tiffany also gets bonus points for doing a cover of U2′s “New Year’s Day” with Front Line Assembly in the late 199o’s.

In the end, Debbie Gibson may have had more career longevity, but both she and Tiffany have a special place in my childhood and musical history. So let’s call it a tie.