This is the 76th post in a weekly series. Read about it here and see the list of previous songs here. A new post about a different song is posted each Monday. You can listen to the songs in a Spotify playlist.

During the 1980s, singer-songwriter Nik Kershaw made it on the charts more than a dozen times in his native England. In 1984 alone, Kershaw had five hits on the UK charts, the most successful being “I Won’t Let the Sun Go Down on Me,” which reached Number 2, “The Riddle,” which peaked at Number 3, and “Wouldn’t It Be Good,” which hit Number 4. Releasing those three songs, as well as writing Chesney Hawkes’s 1991 hit, “The One and Only,” gave Kershaw enough financial stability that he was able to put his kids through private school and then college.

But for all his success in his home country and other parts of Europe, “Wouldn’t It Be Good” was Kershaw’s only song to make it onto the Billboard Hot 100 in the US. That song, from his debut album “Human Racing,” spent 13 weeks on the charts, peaking at Number 46. The song did better in Europe, reaching the Top 10 in Germany, Finland, and Norway.

An earworm because of its crunchy guitars and poppy keyboards, “Wouldn’t It Be Good” had Kershaw lamenting his hard life to an unnamed person:

I got it bad
You don’t know how bad I got it
You got it easy
You don’t know when you’ve got it good
It’s getting harder
Just keeping life and soul together
I’m sick of fighting
Even though I know I should
The cold is biting
Through each and every nerve and fibre
My broken spirit is frozen to the core
I don’t want to be here no more

Wouldn’t it be good to be in your shoes
Even if it was for just one day?
Wouldn’t it be good if we could wish ourselves away?
Wouldn’t it be good to be on your side?
The grass is always greener over there
Wouldn’t it be good if we could live without a care?

The song’s pop sensibility came not just from its infectious riff, but from how he can sing verses of despair in between a chorus that longs for an idealistic alternative. And his delivery sounded equally parts sincere and tongue-in-cheek, as if he couldn’t decide if believed every whiny word he crooned or if he thought the character in his song was obnoxious.

Of all of Kershaw’s songs, “Wouldn’t It Be Good” has been his most covered, with SecondHandSongs listing more than 40 versions. There could be a few explanations for this trend. Among American audiences, this is arguably his most recognizable song, given that it’s the only one that charted. It was ubiquitous on radio and MTV, and two years after Kershaw’s version, a cover of “Wouldn’t It Be Good” received one of the best gifts an ’80s song could get, appearing on the soundtrack for John Hughes’ “Pretty In Pink.”

That slightly more polished version of “Wouldn’t It Be Good” was performed by The Danny Hutton Hitters, led by the Three Dog Night alum. With less crunchy guitar and more synth, this version sound just as earnest as Kershaw’s original. And with Hutton’s throaty voice replacing Kershaw’s nasally tones, it was substantially less whiny.

Belgian band Soulwax included a version of “Wouldn’t It Be Good” on its single “Too Many DJ’s.” The faithful version sounded like Kershaw’s, though stripped down to just guitar and no drums.

The 2000 compilation album “Isn’t She Still…: The ‘Pretty in Pink’ Soundtrack Revisited” featured covers of all the songs on the soundtrack. Project Tru’s cover of “Wouldn’t It Be Good,” which had male and female vocals, messed with the pacing of the song, speeding it up at some points and slowing it down at others. As a result, he chopped-up cover ended up sounding hiccupy and uneven between its slow horns and fast guitars.

Rap group Down Low refashioned “Wouldn’t It Be Good” as a hip hop song for its 2001 album, “The 4th Level.” Other than the recognizable riff, the only part of the original to make it onto this version was Kershaw’s chorus. The rapped verses were new, but fit well over the familiar crunchy guitar.

German dance group Cascada’s 2006 album “Everytime We Touch,” which included a cover of Kim Wilde’s “Kids In America,” also included a dance remake of “Wouldn’t It Be Good.” Like the Down Low version, Cascada’s “Wouldn’t It Be Good” had its own verses in between Kershaw’s chorus. Without the lyrics lamenting “I got it bad/You don’t know how bad I got it,” Cascada’s “Wouldn’t It Be Good” was more optimistic and cheery than Kershaw’s version. Kershaw sounded like he wanted to live without a care because he was burdened with anxiety, but Cascada’s Natalie Horler just sounded like she wanted to dance. And with that Hi-NRG backing track, how could anyone not want to dance?

After covering Dusty Springfield’s “I Only Want to Be with You” on her album “Songs of Love & Loss” in 2007, Tina Arena followed it up the next year with “Songs of Love & Loss 2.” That collection of covers included a stripped-down “Wouldn’t It Be Good” that had no scrunchy guitars and synthesizers in favor of featuring Arena alone with a haunting piano in the background.

Placebo released what is probably the most faithful version of “Wouldn’t It Be Good” when it featured the cover as a B-side to “For What It’s Worth.” Covering a song that was whiny and had crunchy guitars was not a stretch for Placebo, as that is on brand for the band.

On the 2010 covers album “Beat It,” The Mocks turned “Wouldn’t It Be Good” into a sunny tune that sounded like early Ben Folds Five channeling The Beach Boys. In other words, it was full of poppy riffs, harmonies, and back-up singers singing “ahhh, ahhhh, ahhh.” As one does.

If The Mocks’s version sounded like early Ben Folds Five channeling The Beach Boys, then Cliff Hillis’s version sounded like “Don’t Change Your Plans”-era Ben Folds Five channeling Matthew Sweet. Which is a roundabout way of saying that Hillis’s cover, which appeared on the 2014 compilation “Here Comes The Reign Again: The Second British Invasion,” was just as earnest as The Mocks’s cover, but had more piano and some horns.

The following year, folk singer Amy Loftus gave “Wouldn’t It Be Good” a country-tinged makeover, managing to make Kershaw’s crunchy riff sound poppier. And even more infectious.

These covers can either sound cynical or hopeful depending on the singer. Kershaw’s brooding performance fit the vibe of the ’80s, as it was the “me” decade, after all. And Hutton’s less pouty rendition fit perfectly with “Pretty In Pink,” which as an ode to sour pusses whining about what they didn’t have.

The variety of covers in the last three decades should indicate how beloved the song has remained. It was, after all, a big enough hit for Kershaw that he was able to live comfortably off the royalties. It’s a shame he didn’t have more success in the US, but if you’re only going to have one hit in a country, you could do worse.

You can listen to these songs and previously discussed cover songs in a Spotify playlist.
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