Pop Shots – The 3 Most Loving, & The 3 Saddest #1 Songs of Valentine’s Day

Welcome to your weekly dose of pop world musings. Covering all things pop culture, with Valentine’s Day coming up on Wednesday I decided it’s the perfect time to look at some of the songs that have topped the Billboard Hot 100 on cupid’s favorite holiday. I’m not looking for just any #1 songs, however. In honor of the holiday, I’m choosing the three most loving, and the three saddest songs that have been #1 on Valentine’s Day.

Why both sides of the coin? Because I wanted to make sure both those who have, and don’t have, that loving feeling are well represented. Plus, it’s just freakin’ fun to see totally contradictory songs topping the chart on Valentine’s Day. It’s like the entire nation is using their taste in music to show how they really feel.

I’m limiting the musical selections to the ‘80s and ‘90s, so I can come back next year and do it all over again with the ‘00s and ’10s (if I remember)!

Of course, since this is Pop Shots you know everything is seasoned with a little bit of attitude.

The 3 Most Loving #1 Songs of Valentine’s Day 

Whitney Houston – I Will Always Love You (1993)


I don’t think there could possibly be a more appropriate song at #1 on Valentine’s Day than “I Will Always Love You.”

Whitney’s rendition of the Dolly Parton classic would wind up spending a then record 14 weeks at #1, propelling The Bodyguard soundtrack to becoming the best selling movie soundtrack of all-time.

Whitney had a career filled with a lot of amazing moments, and “I Will Always Love You” is either #1, or #2, with only her rendition of the National Anthem before Super Bowl XXV as competition.

Celine Dion – The Power of Love (1994)


Speaking of women with tremendous voices, Celine Dion was at #1 on Valentine’s Day in 1994 with a song that is still a perfect fit for the mood of the day – “The Power of Love.”

Much like Whitney, Celine was a master of knowing how to use her voice. Just because she could go big, didn’t mean she belted out every lyric. She saved her biggest vocals for the most important moments of the song, and that’s one of the reasons why “The Power of Love” works so well, and has become a classic.

Usher – Nice & Slow (1998)


Usher was at #1 on Valentine’s Day back in 1998 with a very specific kind of lovin’ – the knockin’ boots kind!

“Nice & Slow” is a song forever etched in the minds of everyone who is of a certain age for two main reasons – 1. We’re incapable of saying the time seven o’clock without completing the opening lyric of the song, and 2. The spelling lesson midway through somehow became an earworm, and we now all spell Usher’s name in that cadence.

You know what? We wouldn’t have it any other way.

The 3 Saddest #1 Songs of Valentine’s Day 

George Michael – Careless Whisper (1985)


While it was technically a Wham! song, “Careless Whisper” was frequently credited solely to George Michael, which would turn out to be a prescient forecast of a legendary solo career.

Unlike many songs about heartbreak, “Careless Whisper” is heartbreak of a self-inflicted variety, inspired by a time Michael was dating two women (yes, women) at once. It’s painfully gorgeous, and has one of the most memorable sax solos of the ‘80s.

Valentine’s Day in 1985 actually saw the entire Top 5 of the Billboard Hot 100 being all about love, with “Careless Whisper” being the heartbreak at the top.


Exposé – Seasons Change (1988)


As much as it can hurt, sometimes people simply grow apart, and that’s the theme of Exposé’s Valentine’s Day #1 from 1988, “Seasons Change.”

The ballad was the freestyle trio’s biggest hit, and was actually quite the landmark song as it made them one of only two female vocal groups to hit #1 in the entire decade, the other being Bananarama.

Thirty six years later “Seasons Change” is just as beautifully heartbreaking, and wistful as ever.

Toni Braxton – Un-Break My Heart (1997)


In the ‘90s Toni Braxton had a way of making pretty much all of us get into our feelings every time she sang, whether she was heating things up with something sultry, or, in the case of her epic heartbreak ballad “Un-Break My Heart,” inspiring us to relive every breakup we’ve ever experienced.

The fact that this song was #1 on Valentine’s Day is an amazing juxtaposition. “Un-Break My Heart” wasn’t just a one week wonder, however, it stayed at #1 for 11 weeks, and sold more than 10 million copies worldwide, including going triple platinum in the U.S.

Apparently a lot of hearts needed mending in 1997, even – or perhaps especially – on Valentine’s Day.

That’s all for this edition of Pop Shots, but come back next Monday for more shots on all things pop.


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