For our first selection on this list, we went outside the lines a little bit, choosing this melodic track about a woman confessing her feelings to a person, knowing that due to circumstances -- and relationships -- beyond their control, the relationship could never take true flight. The song appeared on her under-appreciated 1996 disc Deborah.
9. Debbie Gibson - "We Could Be Together"
The fourth single from her album Electric Youth album in 1989, this dreamy song became one of Gibson’s last chart hits. The track only peaked at No. 71 on the Hot 100, but the acoustic sound of this one made the song a very charming addition to her stage show.
8. Debbie Gibson - "Staying Together"
One of five Debbie Gibson singles released from her debut disc, Out of the Blue, this track was a No. 22 Hot 100 hit in the United States. But, the up-tempo dance song performed even better abroad -- charting in Ireland, Spain, and the United Kingdom.
7. Debbie Gibson - "No More Rhyme"
There was a sense of an evolution in Gibson’s style that was apparent on Electric Youth, as the third single from the disc was one of the more adult-sounding songs that the teen phenom had released as of yet. Fans of the popular ABC sitcom The Wonder Years may recall Danica McKellar, a.k.a. “Winnie,” appearing in the clip as a cello player.
6. Debbie Gibson - "For Better or Worse"
In 1995, the singer -- five years removed from the Hot 100's top 40 -- released a song that should have been a comeback ticket for the singer, but sadly, radio didn’t notice. But, if you heard it, you were likely as struck as we were by the power and emotion that the singer struck on every line of this Debbie Gibson song. It’s a lyric that she likely couldn’t have delivered as strongly as when she started out. In all honesty, this may be her finest moment. Take a moment and re-discover this one. You’ll be glad you did.
5. Debbie Gibson - "Silence Speaks (A Thousand Words)"
Gibson was in her moment as a songwriter during her peak recording years. Not only was the vocalist, but check the writing credits. On Out of the Blue as well as Electric Youth, she composed both of the entire albums by herself -- including this evocative ballad about a relationship on the brink of extinction, which was featured on the latter.
4. Debbie Gibson - "Out of the Blue"
The title track from her first album, this 1988 single became her third-straight top five Hot 100 hit to kick off her career, as well as her biggest hit on the Adult Contemporary chart to that point. Gibson re-visited this song on her 2010 album Ms. Vocalist.
3. Debbie Gibson - "Lost in Your Eyes"
If you were listening to top 40 or AC Radio in the winter of 1989, there was no escaping this tender piano-driven love ballad, which gave Gibson her biggest hit ever -- peaking at No. 1 on the Hot 100 for three weeks -- and served as the inspiration for likely plenty of romantic moments for couples that year.
2. Debbie Gibson - "Foolish Beat"
In June of 1988, Gibson -- not yet 18 -- made history when this song topped the Hot 100. In leading the charts that week, she became the youngest person to sing, write, and produce a number one hit all by herself. (She still holds the record among women.) The ballad performance was one of her most heartbreaking, allowing this Debbie Gibson song to strike an emotional reaction to the listener.
1. Debbie Gibson - "Only in My Dreams"
The song that launched her career also stands as one of her most memorable. Released in the winter of 1987 -- the singer was just 16 when this song about a girl longing for that special someone after a breakup started to take flight on the charts, peaking at No. 3 on the Hot 100. This was an artist who knew exactly what she wanted to be at an early age -- and she made it all the way to the top, starting with this song.