Farewell, genius. If Sylvester Stewart’s only legacy had been the generations of musicians he influenced (from Miles to Prince) then he’d be a legendary figure, and the way he crossed over to diverse audiences made him an essential cultural trailblazer and industry leader. But the music! The music he produced from the late ‘60s through around 1973 represents one of the most remarkable flurries of creative fertility and vibrancy the world has known – on par with the respective heydays of Stevie, Joni, the Beatles, Coltrane, and so on. His band, Sly and the Family Stone was likewise a cultural force (integrated by both race and gender, and dig those outfits!) and a musical one with the magical combination of Freddie Stone’s soulful guitar and voice, Rose Stone’s grooving keyboards and smooth vocals, Greg Errico’s deep drum pocket, Larry Graham’s deep-throated singing and innovative and influential bass playing, Jerry Martini’s fiery saxophone, and Cynthia Robinson’s authoritative trumpet and endearing vocal exhortations.  

It would’ve been easy to just spew out the hits (yes, this list omits “Everyday People” and “Stand!,” “I Want to Take You Higher,” and “Family Affair,” all songs I can’t imagine living without) and call it a list but the “deep cuts” warrant attention too, so I did my best to balance that while allowing myself the personal biases that are the nature of a list of favorites (including, sorry, the bias against his post-Fresh output, which is endearing but perhaps not at the same level as what came prior).

In roughly chronological order, here we go – note that unless designated otherwise, all of these tracks are by Sly and the Family Stone and dates (aside from #4) are those of the corresponding album releases even if some were recorded the year prior.

1 ) “Run, Run, Run” from A Whole New Thing (1967)

This album predates the hits, but I love it both as a super-grooving record and as a quirky document of Sly’s and the band’s conception as a work in progress. Some of the songs on the record are a bit more polished, but hearing Sly’s extensive soloing on celesta here is just fascinating.

2 ) “Dance To the Medley” from Dance to the Music (1968)

The 1967 single “Dance to the Music” is of course what established the group as a commercial powerhouse, not to mention (with apologies to King Curtis’s “Memphis Soul Stew” and Archie Bell and the Drells’ “Tighten Up”) my favorite-ever “meet the instruments” song to use when teaching. This twelve minute companion piece from the album (which also introduces us “Music Lover,” later made all the more iconic in the Woodstock movie as part of a different medley, with “I Want to Take You Higher”) digs in deeper to exposing us to the individual band members and the infectious layering among them, as well as presenting some of the psychedelic sounds that underscored their relevance to  the Bay Area scene.

3 ) “Plastic Jim” from Life (1968)

This is one of the earliest examples of Sly’s social critique. Sort of a companion piece (if likely unintentional) to Frank Zappa and the Mothers of Invention’s “Plastic People,” this piece eviscerates the superficiality and materialism of the fictional titular character atop a groove that hits so hard that one could (and presumably many did) just ignore it and shake it down, with Freddie Stone’s guitar in particularly fine form.

4 ) “Turn Me Loose/I Can’t Turn You Loose” from Live at the Fillmore East October 4th & 5th, 1968 (1968)

I’ve seen many videos of the original band performing (the Woodstock and Summer of Soul films, as well as various television shows) in the late ‘60s and early ‘70s and every moment of every clip I’ve seen is amazing, so I needed to represent that. Rather than using it as a loophole to shoehorn another hit song on the list, I instead chose to represent their capacity to rave up and demonstrate their foundation in ‘60s soul, in this case with an incendiary medley that mashes up a track from their first record with a (God help me) more-energetic-than-the-original cover of an Otis Redding classic.  

5 ) “Sing A Simple Song” from Stand (1969)

This frequently-sampled track was the song that first got me naively ruminating, at around age 15, about why Sly and the Family Stone wasn’t getting played among the other “classics” of the era on the rock radio stations I listened to. This rocks as hard as anything I’ve ever heard by the Stones and while it may be a “simple song” on the surface, it sure is deep.  

6 ) “Hot Fun in the Summertime” from Greatest Hits (1970)

One of the three new songs included on this hits package (one of the superlative examples of how compilations like this could be meaningful and thoughtful works of art themselves and not just label cash grabs), this relaxed, grooving song features most of the elements that typified the group’s best-loved crossover hits, from subtly thoughtful lyrics to intricately layered production to the communal feeling of the shared vocals, Sly’s own soaring with tremendous virtuosity.

7 ) “Stanga” (single, later reissued on I’m Just Like You: Sly Stone’s Flower Power 1969-1970) by Little Sister (1970)

I wanted to get Sly’s production work for others and this is probably my favorite of those. “Stanga” is a piece Sly wrote and produced for the vocal group Little Sister, which featured his sister Vet Stewart (who had been a Family Stone member on their first album before Rose joined). Though the A-side of this single was the hit, the slinky drum machine-fueled funk production is especially nasty here and foreshadows “Family Affair” and other work from There’s A Riot Goin’ On.

8 ) “Thank You For Talkin’ to Me, Africa” from There’s a Riot Goin’ On (1971)

Though he also guests on the next track on the list, I look at this (and the companion piece “Africa Talks to You”) as bassist Larry Graham’s swan song, demonstrating the possibilities of the slap-and-pop articulation style he trailblazed. But the sheer nastiness of the funk here makes it a worthy epilogue to the iconic “Thank You (Falettinme Be Mice Elf Agin)” and a worthy centerpiece of one of the moodiest and downright greatest albums ever, period.

9 ) “Que Sera Sera (What Will Be, Will Be)” from Fresh (1973)

When one thinks of the formula for slow-burning gospel-infused soul classics, one might not immediately think of a sardonic 1950s pop tune popularized by Doris Day. But here we are. There are a couple other classics on this record, which to many (myself included) represents the bookend of his glory years, and I certainly listen to (and share with students) “It’s Time” and “If You Want Me to Stay” often. But wow, the mix of dark irony and transcendent soulfulness of this performance is still-at-his-peak Sly in full glory.     

10 ) “Remember Who You Are” from Back On the Right Track (1979)

Were the album title only prophetic. I admit that I want to be more enthusiastic about his post-Fresh output, his George Clinton collaborations, his various comeback endeavors, guest appearances, and so on regardless of the explanation of what happened (Questlove’s Sly Lives documentary is extraordinary and a must-watch, so I won’t elaborate here). Still, this is a prime example of the enormous amount of music still inside him past the glory days – he obviously remembered who he was enough to shine at least for fleeting moments.