It can be hard to not engage in a mental game of “What if?” when it comes to artists who died well before their time. Would Kurt Cobain have released more albums as zeitgeist-defining and powerful as Nevermind or In Utero? Would Biggie Smalls have achieved the same elder statesman status as Jay Z or RZA? Would Marvin Gaye have maintained his status as one of the preeminent voices in soul music even amid the rising tide of hip-hop and harder edged R&B?

While the other two artists mentioned above make it harder to make any absolute claims about their imagined futures, I think it’s a little easier to imagine that Gaye would have found a way to thrive even while his peers were pushed into commercial redundancy or started making music that felt beneath their abilities. It feels easy to predict that fate because there’s precedent. Gaye is one of the few Motown artists who came up through the ranks of that label’s star-making system and continued to evolve with the times up until his untimely death one day shy of his 45th birthday.

After some dabblings in doo-wop early on, Gaye positioned himself as a crooner of pop standards like “My Funny Valentine” and “How High The Moon,” before quickly embracing the new sound of R&B and soul. When the mood turned psychedelic, so did Gaye, putting his own spin on Dion and Beatles tunes. Then in the early ’70s, he started writing his own material, deeply personal songs that explored social ills, the ups and downs of his personal life, and yes, plenty of songs about getting it on, all to the tune of sly funk and disco.

By the time of his death, he was showing signs of moving in the direction of quiet-storm soul and world music inspired pop with his final album, Midnight Love. Through it all, that magisterial tenor of his only got deeper and more heartfelt; more sensual and gritty. You can imagine a trajectory that involves him working with Nile Rodgers or Quincy Jones, or finding a way to embrace even more synthetic sounds and electro-pop beats in ways that felt vibrant and original instead of cloying. That we never got to see where he could have gone is one of pop culture’s greatest tragedies.

If there’s any positive to be found amid all the legal clamor regarding the similarities between “Got To Give It Up” and Robin Thicke’s “Blurred Lines,” it’s that it’s great to see Marvin Gaye’s music is still influencing today’s artists and producers. Rappers like Drake and Mos Def have dedicated songs to him. Singers like Michael Bublé and Robert Palmer have tried and failed to capture the gravitas that Gaye brought to even the lightest of pop songs. And his music continues to sell steadily as new generations are introduced to his back catalog. With such a vast and varied career, winnowing this list down to just 10 songs felt like a Herculean task at times. And if you catch me next month, I might rank these differently or include songs that didn’t make the cut this time around. That, again, is what makes Gaye one of the greats. Just as he evolved with the tenor of the times, so, too, does his fans’ appreciation of his work shift and adjust as the years go by.

10. “You’re All I Need To Get By” (from 1968’s You’re All I Need)

The death of Marvin Gaye in 1984 was a huge loss to the musical universe, a still-blazing light snuffed out well before its time. An equally painful departure, and one that was perhaps more devastating considering she was only 24 at the time of her passing, was Gaye’s frequent duet partner Tammi Terrell. As fantastic as the two were on their own (and as Gaye was in the company of other female singers like Mary Wells and Kim Weston), they seemed to bring something extra out of one another. Each was inspired by what they heard and saw in the other — Terrell’s command of a stage, Gaye’s knee-buckling voice — and became the closest of friends. You get the fullest sense of that in this song, that warm regard that glows out of each line they sing. It feels like you’re listening into a conversation between a couple having a cozy anniversary meal together. Sex isn’t on the menu; just a lot of pleasant anecdotes, gentle laughter, and lingering gazes across the table.

9. “I Want You” (from 1976’s I Want You)

Not even Carly Rae Jepsen, in the context of the otherwise-chaste pop song “I Really Like You,” can make the word “want” sound like anything but a sensual come-on. Wrap “want” up in slippery, sweaty, string-soaked midtempo disco trappings, complete with slight groans of pleasure that kick in mere seconds after the music, and that word becomes the hottest thing you’ve ever heard. As with his better-known song “Let’s Get It On,” the heat comes from the spirit of reciprocation. Written by Leon Ware (and originally intended for that artist’s less-than-suggestive album Musical Massage), the lyrics are all about making sure that the door swings both ways: “To share is precious, pure and fair / Don’t play with something you should cherish for life.” Even today that takes some guts for a man to sing about halting a potential tryst before it gets too far so he can make sure there’s real feelings behind this desire.

8. “Is That Enough?” (from 1978’s Here, My Dear)

This album shouldn’t have been as good as it wound up being. As part of the proceedings surrounding his divorce from his first wife Anna Gordy, Gaye agreed to give half of the money he would earn from his next album to his ex. He intended it to be a throwaway recording to just get this particular monkey off his back. It turned into an epic-scale double LP that turned over the details of his broken marriage and ongoing relationship with then-girlfriend Janis Hunter to the tune of synth-drenched and often-delicate funk/R&B. Great as the whole thing is, the apex is this nearly eight-minute track that balances his raw anger and resignation at his ex dragging him through a nasty court fight with one of his more sensual vocal performances and a steamy backing track that cedes three minutes to a duet between Fernando Harkness’ tenor sax and Gaye’s Moog reports.

7. “That’s The Way Love Is” (from 1969’s M.P.G.)

Gaye had yet to really start writing songs, or at least start writing songs that came from deep within his person (sorry, “Hey Diddle Diddle”) by the time he recorded this. Most of his work up through 1970 was trying to make each song written for him or cover song into something personal. It’s a rare skill and one he uses to scale incredible heights on this cover of an Isley Brothers jam. The original is all punch and fire, but inspired by the success a few years earlier of “I Heard It Through The Grapevine,” Gaye and the Funk Brothers turn it into the soulful show of support that songwriters Barrett Strong and Norman Whitfield expressed in their lyrics. So much of this song’s greatness is thanks to the little musical details that give it shape and depth: the dancing Rhodes piano and bass lines that kick it off, the understated backing vocals of session singers the Andantes, and the little swoops of the string section that cut in and out of the mix before taking over the bridge alongside an insistent tambourine. But it’s a great showcase for all of Gaye’s impressive vocal skills, letting him growl and croon while reassuring all of us that he’s had his heart broken a few too many times. If he can survive the pain, surely we can, too.

6. “Distant Lover” (from 1973’s Let’s Get It On)

No song better passes the baton from Gaye’s ’60s swinging R&B era to the unbridled Afrocentric/bodycentric funk/soul of the next decade than this track from Let’s Get It On. Because if this had shown up on one of his albums in, say, 1967, it probably would have been as good, but would have skewed toward treacly ballad territory. You catch hints of what could have been in the strings of the Detroit Symphony and doo-wop backing vocals. In 1973, however, the mood is both sensual and weird. The rhythms slide and glide in a nice slow dance fashion, but the song is driven more by the chicken-scratch guitar line that lingers in the left channel and those synth blips that tiptoe through it all. If Gaye would have recorded it six years or more earlier, it also would have lacked that tone of desperation and angst that he brings to his performance. Listen as the song moves along at how his voice goes from that gentle pleading to an arms akimbo falsetto to something closer to desk overturning anger. Gaye is not about to let that woman walk away without a fight.

5. “How Sweet It Is (To Be Loved By You)” (from 1965’s How Sweet It Is To Be Loved By You)

This is one of the crown jewels of the Motown sound, and a song that came during a jaw-dropping period of greatness by songwriters Lamont Dozier, Brian Holland, and Eddie Holland that included peerless classics like “Come See About Me,” “Nowhere To Run,” and “It’s The Same Old Song.” And it’s a tune that everyone from James Taylor to the Grateful Dead wanted a piece of over the years. That could be attributed to the earworm quality of the song but more so it is a factor of how Gaye sings it. For the then-25-year-old singer, this was like slipping into a comfortable pair of shoes. It’s effortless romanticism that could easily be a heartwarming phone call or post-coital pillow talk. Try as they might, no other vocalist could combine those two sensibilities as Gaye does here, bringing to life the guy that you wanted to bring home to meet mom and then sneak off to the bathroom for a quickie before dinner is served.

4. “Mercy Mercy Me (The Ecology)” (from 1971’s What’s Going On)

The same year that sessions began for this album, Wisconsin senator Gaylord Nelson declared the first Earth Day for April 22, 1970, a chance for U.S. citizens to learn about environmental issues facing the nation. With all that activism in the air, it’s no wonder that Gaye wanted to address those same concerns as part of a song cycle that explored what he saw as a broken and bleeding country. Like a lot of the album, the lyrics are very on the nose, lamenting the “radiation underground and in the sky” and oil-slicked oceans, but that doesn’t make the sentiments any less heartfelt and affecting. The twinkling xylophone and steady heartbeat of the music gives it a tone of hopefulness as well, a feeling that maybe these dire conditions could get turned around if folks would just start to act with a little more care. Compare that to the resignation so many people around the world seem to be experiencing today about the miserable state of our air, oceans, and land. A quaint notion, perhaps, but one that we could all be striving for with this as our soundtrack.

3. “Ain’t That Peculiar” (from 1966’s Moods Of Marvin Gaye)

Try as you might, there’s no way to avoid getting swept up in this song. The production by Smokey Robinson practically begs you to get up and frug along with every overdriven handclap and that insistent melody line that gets doubled up by piano and guitar. This had instant success written all over it. Why then did Robinson and the Miracles hand it over to Gaye and let him be associated with the song far more than its creators? I think Smokey knew that through his voice and perspective, it would have been almost too sweet or too quaint sounding. And goodness knows he’d given his heartaches a platform many times over in songs like “Tears Of A Clown” and “Tracks Of My Tears.” What this song required was an earthiness and slight hint of bitterness to give a truthful root to lines like “The things you do and say are designed to make me blue / It’s a doggone shame my love for you makes all your lies seem true.” For as sunny as he sings it, Gaye can’t hide the hurt he’s feeling.

2. “I Heard It Through The Grapevine” (from 1968’s In The Groove)

The story behind the success of this song — and Gaye’s rendition of it — is one of those tales that lovers of pop music still marvel at to this day. Written by Whitfield and Strong, “Grapevine” was recorded twice in 1967: first by Gaye and later with a funkier arrangement by Gladys Knight & The Pips. And it was the latter rendition that Motown head Berry Gordy gravitated to, releasing it as a single in the fall of that year and winding up with a chart success as a result. When it came to Gaye’s translation, the label founder was reticent to put out another version, instead opting to tuck it away on the singer’s next album. Radio DJs, however, rightfully fell quickly in love with this new, moodier take on the same material, spinning with such regularity that Gordy had no choice but to release it as a single. The result: seven weeks at the top of the Billboard charts and the canonization of both song and singer. Nearly 50 years later, “Grapevine” is as arresting as ever. The threadbare arrangement that puts the emphasis on the string section and that primal drum beat; the Andantes’ unrelenting presence that evokes the whispers that led the protagonist to his revelation. Through it all, Gaye paces back and forth, going over the details of what he heard to his soon-to-be former lover with an air of incredulity to his voice. He just can’t believe that it would come to this. If you listen close at the end, he starts to let a little bit of light in the room. As painful as this moment is, he knows it will soon pass and he’ll have better luck with another sweet young thing. It’s not so much resignation but something closer to acceptance.

1. “Inner City Blues (Make Me Wanna Holler)” (from 1971’s What’s Going On)

In the hands of a lesser singer, there would have been plenty of hollering on this song, or at least a tone of anger to these bleak visions conjured by Gaye and his co-writer James Nyx, Jr. Not even the music created by those two and the Funk Brothers gets up the kind of steam or fury that you would expect to complement lines like “Crime is increasing / Trigger-happy policing” or “Bills pile up sky high / Send that boy off to die.” Instead everyone shuffles through these desperate scenes, shoulders slumped and eyes cast downward. You could holler, sure, but what good what that do? Gaye and Nyx prefer to do the job of reportage, bearing witness to the vast income inequality and broken social structures that plague the inner city. And even with his scintillating falsetto, Gaye goes about breaking everyone’s heart a little bit with each line and each simmering minute of this peerless tune. For as great as the rest of the album that this song comes from is, this one still lingers the longest. And that has everything to do with the fact that the situation in many of America’s inner cities hasn’t improved markedly in 30 years. Just read those lyrics I quoted earlier and see if that doesn’t bring to mind Trayvon Martin or the poor young people with few prospects other than to sign up for active duty. For as great as “What’s Going On” is, the references in it are so specific to the time that it doesn’t resonate nearly as much because of them. Sadly, until some earth-shattering change befalls our capitalist system, “Inner City Blues” is always going to provide a reflection of the current state of affairs. Makes you want to throw up both of your hands, doesn’t it?

Listen to the playlist in full on Spotify.

[Photo by Jim Britt/Michael Ochs Archives/Getty Images.]