30. Roberta Flack – The First Time Ever I Saw Your Face (Ewan MacColl cover)
Let’s start here: Did you know this song was a cover? Well, perhaps you did if you’re reading this site. But Flack’s breakout hit so thoroughly owned the song that preceding versions became irrelevant. Everyone from Gordon Lightfoot to Peter, Paul, and Mary had sung this song in years past, generally keeping it as an acoustic folk number. Flack maintained just enough of that DNA, but brought jazz flourishes. More importantly, though, she brought her voice, which no singer of this song before or since has matched. Ironically, though she released it on an album called First Take, the song didn’t become a hit on its first take. It took its inclusion two years later on the soundtrack to Clint Eastwood’s movie Play Misty for Me to send it to the top of the charts.
29. Plastic Penny – Hound Dog (Big Mama Thornton cover)
Though Plastic Penny uses the rewritten lyrics from Elvis’s version (catching rabbits and all that), the spirit here comes from Big Mama Thornton’s raw blues. They infuse it with a dose of heavy psychedelia, pushing it towards something Canned Heat might have played on the Woodstock stage. These would-be British invaders never quite invaded, but the members went on the bigger and better things: One joined Procul Harum, another became Elton John’s longtime drummer.
28. Levi Smith’s Clefs – You Can’t Do That (The Beatles cover)
Not only was 1969 a big year for Beatles covers; it was a big year for long Beatles covers. Most don’t earn their extended runtimes, but this one does. Led by soul belter Barrie “The Bear” McAskill (weirdly, there is no Levi Smith in Levi Smith’s Clefs), this Australian band roars through a true showstopping performance. The band went through members so fast – 59 musicians came and went between 1963 and 1972 – it’s hard to give credit where it’s due, but if Discogs is to be believed, John Bissett is the man stealing the show on the organ for this particular recording.
27. Fresh Air – For What It’s Worth (Buffalo Springfield cover)
Southern California psych band Fresh Air never went anywhere with their sole album, but it’s become a minor collector’s item in recent years. Though they wrote most of their own songs, A Breath Of Fresh Air (yech) opens with an absolutely storming cover of Stephen Stills’ recent Buffalo Springfield hit “For What It’s Worth.” The entire band races full bore through a frantic stop-start arrangement, only coming up for air for the choruses before diving back into the mayhem. If the slashing guitar solo wasn’t dramatic enough, singer Allen Carey’s throat-shredding yelps in the background add a little extra chaos.
26. Joan Baez – Poor Wayfaring Stranger (Traditional cover)
For someone known as a folk traditionalist, Joan Baez takes some liberties with the extremely traditional “Poor Wayfaring Stranger.” Her voice remains, as always, unimpeachable, but some credit must also be due the session musicians known as the Nashville Cats, who began playing on all sorts of folk-rockers’ albums after Dylan used them in ’66 for Blonde on Blonde. They give the song a funky acoustic rhythm, with little licks popping up here and there. Guitarist Jerry Reed, who plays on this and will appear elsewhere on this list, released his own great cover of this song in ’69.
25. Lloyd Price – Light My Fire (The Doors cover)
One of the most-covered songs of 1969, at one point a half dozen “Light My Fire”s competed for spots on this list. New Orleans soul singer Lloyd Price, best known for a string of ’50s hits like “Lawdy Miss Clawdy” and “Personality” – which gave him his nickname, Mr. Personality – bests the bunch with a soulful, swaggering blast that takes huge liberties with the melody and arrangement. It even looks forward to disco, which was all over the last retrospective list I did, in the backing vocals.
24. Area Code 615 – Lady Madonna (The Beatles cover)
Speaking of the Nashville Cats, Area Code 615 was a band made up entirely of these session musicians (you’ll never guess what city has the area code 615). They somehow still had free time after playing on every prominent folk-rock musician’s record. On their first album of their own, they deliver a wonderful instrumental “Lady Madonna.” Like true collaborators, they trade off which instrument takes the lead every few lines, leaping from fiddle to banjo to harmonica, but play together so well it doesn’t sound scattershot.
23. The Flying Burrito Brothers – Do Right Woman, Do Right Man (Aretha Franklin cover)
Despite having maybe the stupidest name in music history, the Flying Burrito Brothers released one of the greatest country-rock albums ever in 1969 with The Gilded Palace of Sin (we’d call it Americana now, but that term was still years away). Along with a ton of great originals by Byrds alumni Gram Parsons and Chris Hillman, the quartet tackled two numbers by songwriting veterans Chips Moman and Dan Penn. Their version of James Carr’s “Dark End of the Street” is gorgeous. Their version of Aretha Franklin’s “Do Right Woman, Do Right Man” is even better.
22. Albert King – Blue Suede Shoes (Elvis Presley cover)
When you’re name’s King, I guess you have to cover The King. Blues-guitar great Albert King must have thought so at least, releasing the tribute album Albert King Does the King’s Things in 1969. It’s a mixed bag; some tracks suffer from overly elaborate arrangements that drown out the central stars: King’s voice and guitar. But his swinging take on Elvis’s “Blue Suede Shoes” (itself a cover, of course, of Carl Perkins) shines, as the horns and tight Stax rhythm section give his playing a stage on which to shine.
21. Bobby Bryant – Happiness Is a Warm Gun (The Beatles cover)
In a year of a million instrumental Beatles covers, Bobby Bryant’s horn symphony tops them all, swerving through Lennon’s song-mashup “Happiness Is a Warm Gun.” Instrumental jazz covers of pop and rock songs tend to get expansive – just wait until we get to #6 – but Bryant succeeds by keeping things tight. “Happiness” already offers enough zigs and zags to keep this combo quick on its feet, and it’s not ’til the very end that the jazz trumpeter bursts free to pack in some furious soloing, as if racing against the clock.