David Jackson came from working-class England – born in Burton upon Trent, he bounced around a few places before landing in Portsmouth’s Paulsgrove area. Think council housing, not country estates. His parents weren’t thrilled when teenage David demanded they stick a piano in their narrow hallway, but they did it anyway. Fortunately, this was also a good thing, because by the age of 16, he was already earning money playing in local bars, and somehow managed to secure a scholarship to the Royal Academy of Music.

Look Sharp was our introduction to the music of David “Joe” Jackson. What did we think of this young man channeling the musical stylings of the 30s and 40s with lyrics sharply tuned to the zeitgeist of the day? We thought about how much we loved musical surfers not tied to the pop norms of the moment. We thought about how amazing a lyricist he was and not bad on the keys. Now we dive into the music and will update this article each week with new and old tracks that we enjoy and think you will too.

The Look Sharp Revolution

When “Look Sharp!” hit in 1978, it was like getting slapped awake. Jackson wasn’t your typical new wave guy fumbling through three chords. This guy had serious piano chops and wasn’t afraid to use them. His songs jumped from reggae beats to punky attitude to swing club sophistication, sometimes all in one track. And his voice – man, he could sound sarcastic and romantic within the same breath.

Everyone remembers “Is She Really Going Out with Him?” but that song was just Jackson getting warmed up. The deeper cut “Sunday Papers” was where he really showed his smarts, basically calling out Britain’s trashy tabloid obsession years before anyone else noticed it was getting out of hand. While other musicians were still writing songs about cars and girls, Jackson was dissecting media culture.

What made Jackson different was this: he wasn’t pretending to be dumb. While punk was busy celebrating three-chord ignorance, Jackson was showing off jazz chords and complex rhythms. He made being smart cool again, which in 1978 was almost revolutionary.

The Jazz Detour Nobody Expected

After a couple more rock albums, Jackson did something that should have killed his career – he made a swing album. “Jumpin’ Jive” in 1981 was Jackson fronting a full jazz band, doing old standards. Music critics lost their minds. Fans felt betrayed. Jackson didn’t care.

Listening to it now, you realize he was right. The guy could swing. He understood the songs. More importantly, he understood that being an artist meant following your curiosity, even if it meant confusing everyone who thought they had you figured out.

Definitely not some midlife crisis thing either – Jackson was still in his twenties. He just got bored easily and wasn’t about to spend his career repeating himself.

Night and Day Changes Everything

“Night and Day” in 1982 was Jackson’s masterpiece, though he’d probably roll his eyes at that description. The title track became his biggest hit, and for good reason – it’s a perfect pop song that doesn’t talk down to you. Latin rhythms, sophisticated chord changes, lyrics about adult relationships, all wrapped up in something you could dance to.

The whole album felt like Jackson had figured out how to be commercially successful without selling out his brain. Songs like “Real Men” tackled gender politics with more intelligence than most sociology papers. “Steppin’ Out” was pure nightlife glamour. “A Slow Song” was genuinely touching without being sappy.

The Classical Years (Yes, Really)

Then Jackson disappeared into classical music for a while. Albums like “Will Power” weren’t rock star vanity projects – they were serious compositions that got performed by actual orchestras. Classical music critics took him seriously, which probably annoyed a lot of people who had fancy degrees and couldn’t write a pop song to save their lives.

The classical work fed back into his later albums. You can hear it in the arrangements, the way he thinks about melody and harmony. It’s like he went to graduate school for ten years and came back a better songwriter.

Still Surfing After All These Years

Jackson never stopped changing. “Rain” in 2008 showed an older artist still pushing buttons, refusing to play it safe. “The Duke” was his tribute to Duke Ellington – not covers exactly, but Jackson’s take on Ellington’s compositions. It was brilliant in the way only Jackson could pull off.

His most recent album, “Fool,” proves he’s still got it. Still writing songs that make you think. Still playing piano like his life depends on it. Still being Joe Jackson, which means you never know what’s coming next.

What Makes Joe Jackson Special

Look, Joe Jackson did something most artists never pull off – he stayed interesting for decades. Most musicians find a formula that works and then overuse it. Jackson got bored easily and kept switching things up, dragging his fans along for the ride whether they liked it or not.

He also never talked down to people. Record labels in the ’80s thought audiences wanted everything dumbed down, but Jackson kept writing complex songs with actual ideas in them. Turns out people were hungry for music that treated them like they had functioning brains.

These days, when every song gets tested by algorithms before anyone hears it, Jackson’s career seems almost impossible. Imagine telling a record executive you want to make a jazz album, then a classical album, then go back to rock but with Latin influences. They’d laugh you out of the building. But Jackson made it work because he never pretended to be something he wasn’t.

Jackson was doing what everyone talks about now – following your passion, being authentic, not letting other people define your limits. He just did it when record companies actually had power and radio stations could make or break careers.

The Weekly Deep Dive Starts Here

We’re going to spend the coming weeks exploring Jackson’s catalog, from the obvious hits to the deep cuts that only the obsessives know. Each week, we’ll pick tracks that show different sides of this restless artist’s journey.

Some will be from the famous albums. Others will be B-sides, live versions, collaborations you’ve probably never heard. All of them will be Joe Jackson being Joe Jackson – unpredictable, intelligent, and never boring.

Starting next week: “Sunday Papers” gets the complete treatment, because any song that predicted our current media landscape deserves closer attention. Plus, it rocks.

1) *Paulsgrove is an area of northern Portsmouth, Hampshire, England. Initially a small independent hamlet for many centuries, it was admitted to the city limits in 1920 and grew rapidly after the end of the Second World War.   

1) Paulsgrove – Wikipedia. https://en.wikipedia.org/wiki/PaulsgroveNext week: Sunday Papers – How Joe Jackson Predicted Social Media Outrage in 1978