Jun 272025
 

Head back to the beginning.

10. Pee Wee Herman & Friends — Sly and the Family Stone Medley

This is gonna sound like a crazy conspiracy theory, but here goes: Pee Wee Herman introduced an entire generation to the music of Sly and the Family Stone.

Okay, maybe not an entire one, but for sure a very specific subsection of the population, namely TV-obsessed American kids and teens in the early ’80s. For years, I’d thought I was the only goofball inspired to buy their first Sly record because of Pee Wee. Then I saw YouTube comments attached to the video above and did a little online digging and discovered that I was far from alone in this experience and that Pee Wee’s leading the children to Sly was an actual thing.

How did this happen? Well, in 1981, HBO broadcast the first Pee Wee Herman TV special (The Pee Wee Herman Show). Recorded live in Los Angeles the year before, it was absurd, kitschy and hilarious, home to a handful of lovably eccentric inhabitants, with Pee Wee (aka Paul Reubens) leading the way. During the show, he and his next-door neighbors, the Jelly Donuts (played by Monica Ganas and Brian Seff), perform a musical salute to Sly Stone. It is pure, unadulterated joy and undoubtedly the greatest live cover performance of a Sly medley in human history. As an added bonus, it includes a proto version of the soon-to-be iconic Big Shoe Dance as seen in 1985 film Pee Wee’s Big Adventure.

To this day, whenever I hear “Hot Fun in the Summertime,” I always insert a Pee Wee style “OOOH-ARGHHH” before the chorus. Thanks Sly, you genius. And on behalf of the kids, thank you Pee Wee/Paul for being yours-elf. “OOOH-ARGHHH”! — Hope Silverman

9. H.E.R. — Dance to the Music

This faithful cover has all of the essentials: scatting, big-band brass, the mix between deep and punchy vocals, the pleasant whiplash you get when most of the big sound elements suddenly drop out. It’s the feel-good song we know and love, though some common elements, like the organ, take a more prominent role here. I’m surprised not to hear more overt minion participation in the chorus parts though given this song’s place on the Minions: The Rise of Gru soundtrack. A missed opportunity by producer Jack Antonoff? Maybe it’s best to avoid an over-cheese effect. — Sara Stoudt

8. Joan Osborne — Everybody Is a Star

“Everybody Is a Star,” the b-side of the “Thank You (Falettinme Be Mice Elf Agin)” single, was the end of the “classic” era for Sly and the Family Stone. It would be nearly two years before the release of “Family Affair,” which lacked most of the Family Stone other than Sly and his sister Rose, and the music began to turn darker and more political. “Everybody Is a Star,” is a gospel-inflected soul ballad, featuring members of the band describing how each individual is special. Although the general uplifting nature of the song does give way to some uncertainty, when it discusses falling stars. Joan Osborne included the song on an all-covers album How Sweet it Is, released as a reaction to the 9/11 attacks. Her version takes a soulful, mostly acoustic approach, leavened by some tasteful tenor sax and trumpet. — Jordan Becker

7. Dillard Hartford Dillard — The Same Thing

This cover brings the same straightforward delivery of the lyrics, but it goes country with the style. Banjo fans rejoice! The Charlie Brown adults’ speaking noises never sounded so cool as in the original, but not to be outdone, here the twangy banjo first goes all out as a replacement. Then other sounds take turns during this “wah wah” phase; each time, a different character appears. A kazoo, a distorted harmonica, tinkly chimes, the banjo again (this time with a new pluck pattern), even a fiddle at the very end… the family twang is all here. — Sara Stoudt

6. Walter Sickert & The Army of Broken Toys — If You Want Me to Stay


Boston-based Walter Sickert & The Army of Broken Toys decided not to overthink it: the song’s signature bass and vocals remain prominent in their cover. But the feel is completely different: the track is super echoey, with whispered backing vocals and every instrument other than the drums, bass and lead vocal seemingly piped in from a different room. The horn part is here, played by a guitar with an effect, buried way deeper in the mix than the original. As the cover builds to its conclusion, strange things start to happen: drum fills seemingly out of time, weird edits, the occasional extra vocal. Though it never fully announces itself as capital-W weird, it’s pretty aggressively arty, as you might expect by someone who self-describes his sound as “Dada-esque.” And despite honoring the bassline, the funk is sapped out of the song for something more akin to post-punk. — Riley Haas

5. British Electric Foundation ft. Lalah Hathaway — Family Affair

B.E.F. snag this catchy refrain and incessant beat and recognize that it’s a perfect fit for the type of electronic dance music being made in 1991. Singer Lalah Hathaway elevates the original’s low-key and lower register vocals to a soulful and groovy new level and the song slowly adds in funkier elements. The little guitar licks that come through are a nice callback to the Sly version, but the drums in particular are the musical star sharing the spotlight with Hathaway’s chorus of voices. Both versions will get you on the dance floor, but the B.E.F. song has more of the pop sensibility the early ’90s was known for. — Mike Misch

4. Diana Ross — Le Lo Li

A deep cut from Sly’s first credited solo album, “Le Lo Li” is one of those nonsense songs of his that is just remarkably catchy and remarkably well arranged. Ross’s version is the only notable cover of this song, but for decades nobody knew about it. It was recorded for her self-titled seventh album released not long after Sly’s “solo debut” but not released until a 2012 reissue. As was her wont then, she takes Sly’s funky original and discofies it. She speeds it up so that the feel is now entirely disco rather than funk. The arrangement is stripped down to the bass and drums, a very busy organ and Ross’s vocals. The piano intro is still there for the briefest moment but disappears. That piano provides some equally brief punctuation midway through the song until there is an extremely jazzy piano solo late in the song. Ross’s voice sings the hook almost more relaxed than the original, but the verses are as uptempo – almost rushed – as the beat is behind her. It’s soulful disco that becomes basically disco-jazz for the climax. — Riley Haas

3. Magazine — Thank You (Falettinme Be Mice Elf Agin)

With the original as funky as a barrel of snakes, it might seem quite a jump for Howard Devoto and his ascetic brand of aquiline punk to carry off. Yet carry it off he does, and more, in no small part to the guitar of John McGeoch, later of the Banshees, and, especially, Barry Adamson, later one of Nick Cave’s Bad Seeds, on bass. Add in the keys of Dave Formula and there is the belated realization as to quite what a heavyweight band this was, if largely unrecognized at the time. The vocals are harsh and brittle, and the overall is a precedent for goth. I can imagine a dancefloor of pale and painfully self-conscious beings, flailing about, unsmilingly. — Seruas Og

2. The Dirtbombs — Underdog

The Dirtbombs are a Detroit-based garage-rock group that first formed in 1995. Known for their unique blend of rock, soul, and punk, this band is fittingly described as being gritty or even sleazy in the best of ways. Somehow, it makes a lot of sense for the words “Dirtbombs” and “Underdog” to be in the same sentence.

The opening guitar line has undergone the garage rock treatment; it’s tinny, raw, and oddly charming (detuned Frere Jacque, avec incorrect notes). As it rumbles into existence, one wonders where it’s all going. Next up, Mick Collins’s effortless voice starts the song at a running pace: “But they won’t let you forget that you’re the underdog and that you’ve got to be twice as good.”

The original “Underdog” was written by Sly in 1965 (for the San-Fran-based Beau Brummels) but wasn’t released until much later. In this version, somewhere between that tinny guitar, the smooth yeah-yeahs, light-footed drummer, and effortless sing-talk vocals, The Dirtbombs make some sonic magic, owning “Underdog” as if it were their own. — Aleah Fitzwater

1. Bettye LaVette — Thankful n’ Thoughtful

In Sly’s hands, “Thankful n’ Thoughtful” is delivered as a slice of prime clavinet-infused boogie that sashays along with ants in his pants. But LaVette takes it down to the levee, on a slow boat through the swamps. As such, she finds whole more depth in her gratitude; you feel she really means it. Of course, however distinctive Stone’s voice may be, LaVette is one of those rare few who can pick up a song by anyone and make it better. You read that right: her versions of songs by singers can be as varied as Sinead O’Connor, Nat King Cole and Van Morrison, yet she makes them all her own. Mind you, she has done one hell of a lot of covers, in her near-to-eight decades, with no signs of stopping any time soon. — Seuras Og

Check out more installments in our monthly ‘Best Covers Ever’ series, including the Rolling Stones, Kate Bush, The Beatles, and more.

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