When the Boys Cover Whitney Houston #4: "Didn't We Almost Have It All," by Michael Masser & Will Jennings, 1987

Andy, of the entertaining "The Vinyl Room," joins us again for our FRONT ROW & BACKSTAGE continuing series, as we continue our romp through a legend's catalog! This time, a yearning, heartfelt ballad.

Welcome to Part 4 of our musical road trip to the hits of Whitney Houston from a male perspective! We’re pleased to have

Andres

(aka Andy) of Substack’s popular The Vinyl Room joining us again to offer his talented ear, singing voice and expertise, and unique writing style (from his UK home…or, in this case, just in off the beach, recently, from the Mexican Riviera)!

Since Whitney’s award-winning career began in the mid-’80s, she’s not only had an abundance of mega-hits, but many recording artists have covered her hits, including a surprisingly large number of male artists!

Please enjoy our debut edition of “When the Boys Cover Whitney Houston,” here, as we dug deep into her “Saving All My Love For You” and “How Will I Know” with some striking covers by select male artists!

A Little Context

“Didn’t We Almost Have It All” was recorded by Houston for her second studio album, Whitney (1987). It was her 9th single released by Arista Records in her fourth year with the label. It would become Whitney’s 5th straight #1 hit in a run of seven consecutive chart-toppers!

“Didn’t We Almost Have It All” was the second single released from her Whitney album, following her landmark “I Wanna Dance With Somebody (Who Loves Me),” a record that broke all records by amassing sales of over 14 million units, worldwide!

“I Wanna Dance” hit the #1 spot in 8 of 10 countries! The two lone countries where it fell short? Ireland (“only” #2) and Austria, where it needed a little ‘alp, as it couldn’t climb its way past #3 (she should’ve yodeled)! Andy and I covered that ground-breaking song here:

🎤When the Boys Cover Whitney Houston #3: "I Wanna Dance With Somebody (Who Loves Me)," Merrill & Rubicam-1987

“Didn’t We Almost Have It All” was written by Michael Masser and Will Jennings and produced by Masser. This was the third Masser-composed collab recorded by Whitney (following “Greatest Love of All” with Linda Creed, and “Saving All My Love For You” with Gerry Goffin).

By this point, Masser was all but becoming the go-to songwriter for Houston, whether or not he wrote with her in mind. Case in point: While he co-wrote (with Gerry Goffin) her 1985 #1 smash, “Saving All My Love For You,” it was originally recorded in 1978 by Marilyn McCoo & Billy Davis, Jr. (produced by Masser and Davis, Jr.):

The Queen “B”

Initially, Houston’s cover of The Isley Brothers’ “For the Love of You” was intended as the second single from the album. However, as Houston’s career was being intentionally and carefully crafted, Arista founder and president, Clive Davis (and the label’s A&R staff), decided to release “Didn’t We Almost Have It All,” believing that all the singer’s material should be original.

The song was released as a single in July 1987. Whitney’s Isley cover, however, ended up as the B-side to her next single, the hit, “So Emotional,” in November 1987. In fact, her version of “For the Love of You” earned her a nomination for Best Female R&B Vocal Performance at the 1988 Grammy Awards! Even her B-sides are special!

The Song

“Didn’t We Almost Have It All” received positive reviews from most critics, who praised the song’s lyrics, Masser’s production, and of course, Houston’s vocal performance.

There was some critical snark, however, for the song, most notably from well-regarded rock critics, including Los Angeles Times editor, Robert Hilburn, who wrote, “Houston’s stardom will be boosted most by ‘Didn’t We Almost Have It All,’ a sweeping Masser/Jennings ballad with the kind of big, emotional finish that will make Liza and hundreds of other singers wish they had been given first crack at the song.”

Rolling Stone’s Vince Alleti, similarly opined, “Masser reprises the show-tune schmaltz of ‘Greatest Love of All’ in his even cornier ‘Didn’t We Almost Have It All.’”

At the 1998 Academy Awards (l-r), lyricist, Will Jennings, singer Celine Dion, and composer, James Horner. From the May 29, 2024 Tyler (TX) Today Magazine: “Before Celine Dion powerfully sang the romantic theme song from the motion picture, Titanic, East Texan native Will Jennings had penned the dramatic lyrics for ‘My Heart Will Go On.’ The song earned Jennings his second Academy Award for Best Original Song, having won the Oscar fifteen years prior for ‘Up Where We Belong,’ from the movie, An Officer and a Gentleman. Jennings would go on to write more than 500 songs which would be performed around the world by some of the most talented artists of our time.”

Lyricist, Will Jennings (above left, in 1998), in an interview with Songfacts, revealed that “‘Didn’t We Almost Have It All’ is a song about wishing for reunion with someone, and making the case for it by recalling past good times.

“I think that probably took longer than any other song [to write]. Michael [Masser] was traveling and he was in the studio and doing this and that, so I think it was about a year or two after we started it that it was finished.

“And, I sort of lost track of the whole thing. I don’t know how many times I rewrote bits and pieces of the tune. I remember distinctly that we ran (up) over two hundred dollars worth of phone calls from a hotel in Nashville! Of course, it was well worth it in the end.

“It was one of those never-to-be-repeated experiences, because he was producing the record and he wanted to really nail it down. He kept feeling it wasn’t finished and so he’d put it away, and I was off working on something. I’d lost track of what went on with it.”

Early domestic live performance of the song, 1987 at Saratoga Springs, NY:

Live at London’s Wembley Stadium, 1988:

The Covers

Andres

, and his take:

The assertion that a Whitney song is difficult to sing is as old as yesterday’s news. Nothing in her repertoire is precisely what you would call a walk in the park, but this particular tune always ranks pretty high in virtually every “Toughest Whitney Songs to Sing” compilation I’ve seen over the years.

One could argue it’s that tricky, unforgiving tempo. Those quick transitions into head voice and back into chest. The key-change in the chorus. The high belts. That bridge.

In fact, it’s all these elements combined, all at once (sorry, I had to!) that could destabilize some of the most accomplished singers out there.

You see, it’s not just the 2 octaves and five notes you’ll need to have available, all nicely connected, at the snap of a finger. The levels of strength and stamina this song requires are arguably among the most advanced in contemporary singing.

Let’s be honest—very few singers are at Whitney’s level. Most of us mortals, when trying to cover this song, would need to leave at least something behind.

If it helps, I’ll tell you what you definitely cannot do without: vocal dynamics.

Loosely defined, these include any variations in pitch, volume, pace, tone, occasional pauses, and generally all the aesthetic resources singers use in order to convey emotion and deliver an impactful performance.

From the gentlest of whispers to that dramatic, heart-wrenching climax, a strong command of vocal dynamics is non-negotiable if you want to do this song justice.

That’s what I decided to focus on when analysing the covers today.

Filipino singer, Jed Madela (above; he’s now 47), does a pretty good job at recreating the dramatic mood crescendo of the original in his 2015 cover (video just below). He had the guts to tease the tempo quite early on in the first verse, which I felt was a sweet nod to Ms. Houston, as she would often do the same with her own songs, especially when performing them live.

Yet, not even Jed’s studio-perfect environment can hide the fact he then had to pay for his chutzpah by taking a couple of extra (unplanned) breaths mid-sentence. Still, I celebrate his bold moves, and how he raised the stakes (and a couple of notes) at the end. Very decent work (Iconic album produced by Madela and Jonathan Manalo).

[By the way, Madela possesses the vocal range of a countertenor (equivalent to that of the female contralto or mezzo-soprano voice types), spanning from his lowest note at F#2, to his highest note at B♭5.]

But, it was Daniel Briones who impressed me the most: His 2023 cover taps into a sweet, gentle vulnerability which gives the song an interesting twist. Matters of the heart tend to trigger a wide array of feelings and emotions in each of us. Right from the start, Daniel makes it clear that this is his story to tell.

I like how he holds onto that sense of restraint for most of the song whilst still keeping things interesting by adding some tasteful (and well-executed) melisma. You know he’s got more in the tank, but he’s letting things simmer.

When he gets to the bridge, he astutely throws in some staccato notes as he’s heating things up, thus creating a smooth transition from his earlier sweetness into the most dramatic section of the song. It’s called a bridge for a reason, and this is what I call smart singing in action.

For the big note, I loved how he went into that beautiful falsetto, as opposed to belting it all out. This was the perfect progression from his earlier sweetness and vulnerability. Technically brilliant and aesthetically beautiful. I’m sure Whitney would have been proud!

Brad’s Cover Choice: Stefan Borsch, 1987

Stefan Borsch, solo in the ‘80s (r), and (l) with ‘70s dansband, Vikingarna (aka The Vikings), the best-selling dansband, and one of the best-selling artists in Scandinavia, and is often regarded as the greatest dansband to have existed. At the time of its 2004 dissolution, it had sold more than 11 million records. Borsch was in Vikingarna from 1973 to 1979.

While Whitney was rocketing to the top of worldwide charts with both her “I Wanna Dance With Somebody (Who Loves Me)” and “Didn’t We Almost Have It All,” Swedish singer, Stefan Borsch, was the first to tackle the Jennings lyric in a language other than English!

Fellow countryman, songwriter Christer Lundh, translated the lyrics into Swedish for Borsch’s 1987 album, Dansa en dans med mej (“Dance a Dance With Me”):

Bosch, 77, was active in Swedish dance band music between 1965 and 1999 and was lead singer of Vikingarna, 1973 - 1978. Somewhat predictably, he doesn’t take too many chances in his interpretation (especially given his dance band experience and fan base), but he offers a solid performance with his smooth tenor atop a string-laden arrangement (produced and arranged by Bert Karlsson and Anders Engberg)….“Låt det bästa stanna kvar”:

In a bit of delicious musical serendipity (which we here at FRONT ROW & BACKSTAGE always love!), our Tune Tag friend, Dave, of

Music Influence

, also wrote a Whitney-related article he published the same day as this one! Catch his Tune Tag appearance by clicking here, and please take in his wonderful Whitney piece, here:

From Dolly to Whitney: The History of “I Will Always Love You”