Chart Beat Podcast: The Hot 100's Top 40 This Week in 1987, Part 2 … With Special Guest Debbie Gibson

Madonna, Debbie Gibson & Michael Jackson
Getty Images; Design by Jessica Xie

Madonna, Debbie Gibson & Michael Jackson

Classic songs by Madonna, Michael Jackson & more highlight Nos. 20 through 1, as Gibson celebrates the 30th anniversary of her debut album, "Out of the Blue."

Welcome to the Billboard Chart Beat Podcast, where each week co-hosts Gary Trust and Trevor Anderson, from the Billboard charts department, discuss why what's on the charts … is on the charts, while also looking at current chart action in a historical context for even greater insights.

This week, Gary and Trevor continue counting down the Billboard Hot 100 this week 30 years ago – Aug. 29, 1987! In the second half of a two-part episode, following last week's Nos. 40-21 rundown, we recap Nos. 20 through 1. As the numbers get smaller, the hits get bigger (to borrow from Casey Kasem), with songs by George Michael, U2, Michael Jackson, Whitney Houston and Madonna all in the top 20. Plus, as Luis Fonsi and Daddy Yankee's "Despacito," featuring Justin Bieber, leads the current Hot 100 for a record-tying 16th week, 30 years ago the chart welcomed its first Spanish-language No. 1.

Meanwhile, Debbie Gibson joins the podcast to recap the 30th anniversary of her debut album, Out of the Blue. On the Aug. 29-dated Hot 100, the set's lead single, "Only in My Dreams," became her first top five hit, while the album would enter the Billboard 200 a week later on its way to a top 10 peak in 1988. The set would generate four top five Hot 100 hits, including her first No. 1, ballad "Foolish Beat."

"Those were my favorite songs from four years of diligently writing pop music," Gibson says of the LP. (On Aug. 29, 1987, she was two days shy of celebrating her 17th birthday, or "arrival" day, as she dubs it; thus, this podcast is posting on her latest special day!) "I had a lot to choose from. That whole batch of songs really became the foundation of my style."

Having started in the industry so young, just like last week's podcast guest (and Gibson's good friend – they were never rivals), Tiffany, Gibson can relate to another star, one especially in the news this week, who launched her career as a teen, Taylor Swift, in terms of beginning with an authentic image (as opposed to industry executives largely dictating such a personal direction). "I just look at [Swift] and think, even the songs that she co-writes are her. They're quirky. They're connected to her life [and] her fans. You can tell it's an extension of her," says Gibson (whose first box set, We Could Be Together, is due Nov. 3).

"It's not about being the slickest vocalist, or having the cleverest song. I think it's about that connection, within yourself and to your audience. To keep that going at all costs … I think that's the key to all of it."

Enjoy the entire latest Chart Beat Podcast and check back for more upcoming episodes with artists, label executives, radio programmers and personalities, songwriters, producers and more. And, to receive every episode automatically in your inbox, subscribe to (and rate) the Billboard Chart Beat Podcast on iTunes!

(Up next week: we'll discuss Swift's "Look What Made You Made Me Do," which appears headed for No. 1 on the Hot 100, and speak with two Houston radio programmers about how their stations are helping listeners through the area's devastating storm.)

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