Much like our 100 Greatest Covers post last year, this was a collaborative effort for the Popdose staff. Although our list of nominees was a bit smaller – only 300 songs – the voting was every bit as competitive, with our #7 and #8 songs being separated by just one tenth of a point. As a collective, we wish you a happy Valentine’s Day, whether you’re a member of a Bizarre Love Triangle, a pair of Two Hearts, or even if you’re a member of the Lonely Hearts Club. Love to all. — Zack Dennis
If you’re listening on Spotify, you can find a link to versions of all of the songs here.
100. “You Belong to Me” – Bob Dylan.
Of all the things that can cause friction in a relationship, physical distance can be one of the hardest to endure. It softens a couple’s strengths, and makes every single problem – even the smallest ones – harder to address. Without a definitive end in sight, very few long-distance relationships survive. And yet, almost all of us have been willing to give it a shot at some point, because it’s worth it to us to see if we can beat the odds. “You Belong to Me” isn’t particularly specific about when a reunion is expected – but there’s definitely a happy ending in sight. The song was first recorded in 1952 by Sue Thompson, and has been covered by an endless list of artists since, including Bing Crosby, Ella Fitzgerald, Crystal Gale, Dean Martin, Patsy Cline, Marshall Crenshaw, Rod Stewart, and Tori Amos. The punk band The Misfits even tried their hand at it. As far as Billboard is concerned, the most popular version was Jo Stafford’s 1952 recording, but my personal favorite has always been the version by Bob Dylan that was included in the 1994 film Natural Born Killers. Dylan’s voice was never stellar to begin with, and has deteriorated steadily over his long career, but the thin rasp of his voice fits perfectly here with a single acoustic guitar, singing of a lover off exploring the world, enjoying the splendor of exotic locales, but ultimately destined to return home to their one true love. — Zack Dennis
99. “I Say a Little Prayer” – Aretha Franklin.
As anyone who reads Popdose’s “Digging for Gold” series knows, I’m no fan of the Bacharach-David-Warwick triumverate’s ’60s oeuvre. Where others hear melodic invention and lyrical sophistication, I hear pretentious cheese, masturbatory trumpet obbligatos and an inauthentic vocalist with a 10-foot stick up her ass. That’s why I get such joy from Aretha’s cover of “I Say a Little Prayer,” which replaces the usual staidness with a boatload of soul — and ditches Dionne’s prissiness in favor of a loose, almost tossed-off revelry. In Aretha’s assured hands — and with name-above-the-title-worthy assistance from her backing vocalists, the Sweet Sensations — the song becomes at once both spiritual and transcendently earthy and playful, its protagonist’s mundane musings rendered exultant thanks to those interrupted verse lines and irresistible call-and-response choruses. By investing “I Say a Little Prayer” with the trappings of the church, ReRe cut through B&D’s pretentions and finally brought one of their songs into the world where people actually live. — Jon Cummings
98. “Genius of Love” – Tom Tom Club.
Whatcha gonna do when you get out of jail, Tina Weymouth and Chris Frantz of Tom Tom Club, by which I mean form a side project to get out from under the oppressive, pretentious thumb of your Talking Heads bandmate David Byrne? Fun. Natural fun. Which is form your own cool New Wave band and make a playful, joyful club jam for adults/crush mixtape staple for quirky teens but which will sadly be ultimately shadowed by Mariah Carey’s pathological need to repeatedly sample it. Still, this song so succinctly captures those tipsy, giddy feelings of the beginnings of a new relationship. –Brian Boone
97. “Cupid” – Sam Cooke.
It’s not as romantically inclined as “You Send Me”; it’s not as saccharine as “(What a) Wonderful World”; no, somehow “Cupid” lands somewhere in-between the two, with Cooke pleading his case to the little winged cherub. Here’s the thing, though: the sound effect of the arrow being fired and hitting it’s target makes the whole thing a bit too literal.
— Michael Parr
96. “And I Love Her” – The Beatles.
This might be Paul McCartney’s first great love song, emerging as one of the standouts on a record dominated by his songwriting foil John Lennon, A Hard Day’s Night. It’s also a rare moment of perfect quiet amid the churning guitars and pounding drums of the group’s Beatlemania era. Like so many of McCartney’s most shining tunes, the words aren’t going to win any poetry contests. “Bright are the stars that shine/Dark is the sky/I know this love of mine/Will never die,” he sings, and it’s like he thumbed through some poor sixth form’s diary for inspiration. Aw hell, who am I kidding? He’s frakking Sir Paul McCartney. He could fart into a microphone and I’d at least listen once. But the melody, ah, the melody–no man in the twentieth century has played vessel to so many effortlessly perfect melodies, and “And I Love Her” is no exception. It aches. — Matt Springer
95. “For Emily, Whenever I May Find Her” – Simon & Garfunkel.
I don’t know how to explain this, the song that turned me into a hopeless romantic from the first time I heard it as a 9-year-old. So I won’t try. Instead I’ll just reprint its emotionally engorged lyric: “What a dream I had! / Pressed in organdy / Clothed in crinoline of smoky burgundy / Softer than the rain / I wandered empty streets down, past the shop displays / I heard cathedral bells tripping down the alleyways / As I walked on / And when you ran to me, your cheeks flushed with the night / We walked on frosted fields of juniper and lamplight / I held your hand / And when I awoke and felt you warm and near / I kissed your honey hair with my grateful tears / Oh, I love you, girl / Oh, I love you!” — Cummings
94. “Swing Life Away” – Rise Against.
“Swing Life Away” isn’t a sell-out song. The sound is very much a departure from Rise Against’s usual straight edge punk, but the sensibility is authentic. It’s a song of struggling in the city, trying to get by on minimum wage, and that near-universal act of new love, comparing scars. We get by with love and with friends and good music. The video is excellent, too, with its great scenes of Chicago including the image of the Virgin Mary that many believed could be seen on an underpass of the Kennedy Expressway. It just goes to show that there’s a lot of romance in everyday life, romantic and otherwise. — Annie Logue
93. “Samson” – Regina Spektor.
Many of Regina Spektor’s songs are self-contained stories, and “Samson” is no exception. While the biblical version of Samson and Delilah is one of the most famous and familiar love stories of all time, Spektor adds a different twist to the tale. It’s open to interpretation whether her song is the story of Samson’s unknown first love, or an alternate history of his affair with Delilah, but there’s no question that the anonymity of the couple in her story provides for a happier ending than the sordid and tragic tale originally told in the Book of Judges. Personally, I prefer the version of this song from Regina Spektor’s 2001 album Songs, than the one that was re-recorded and released with Begin to Hope in 2006. The new version is too quick and light – the original version has less polish and is heavier in a way that makes it feel so much more emotional, and dampens my eyes just a little bit every time I hear it. — Zack Dennis
92. “The Look of Love” – Dusty Springfield.
It figures that my favorite Dusty song is one that hardly makes use of her belting, soulful contralto. There have been more commercially successful covers of this, one of the finest Bacharach/David compositions, but none matches Dusty for sheer sensuality. Bacharach claims the melody was inspired by watching Ursula Andress in an early cut of Casino Royale, and I believe it. And that sultry, Stan Getz-inspired sax solo? Timeless. — Chris Holmes
91. “You’re My Home” – Billy Joel.
According to Joel’s Songs in the Attic liner notes, this was written as a Valentine’s Day present for his first wife, because he had no money for roses or chocolates. That we’ve all been the recipient of such a heartfelt, eloquent gift says something about the capacity of a great song to be universal, of a single sentiment to be so true for so many. It’s also pretty easy to sing, and it always helps the young romantic to have a decent serenade or two ready and available when wooin’ the ladies. Not that I’d know anything about that or nothin’ … — Rob Smith
90. “Fairytale of New York” – The Pogues.
It’s widely recognized as a Christmas song. Fair play. But that doesn’t mean there’s not a virulent strain of contagious, infected, decaying romance at the heart of Shane MacGowan’s ode to New York City at the holidays, a duet with Kirsty MacColl written from the point of view of two alcoholics falling in and out of love in the span of a night in the drunk tank. MacGowan’s slurred response, “I kept ’em with me, babe/I kept ’em with my own” remains gutting decades after release and constant overplay every holiday season. — Springer
89. “You’re My Best Friend” – Queen.
Sure, Queen (usually Freddie and Brian) had written love songs before on the albums prior to Night at the Opera, but none of them had the wholehearted sentiment of this John Deacon composition, written for his wife, Veronica, to whom he remains hitched to this day (so there’s no doubting his sincerity!). The song’s construction itself is a great example of Queen at (I insist) their peak, with its sumptuous Roy Thomas Baker production, jaunty melody, layered harmony vocals, and Brian May’s sprightly solo all standing out. Mercury sings it, as he often could when he wanted, without a trace of irony or smirkiness- and that makes all the difference. While not a big hit single in 1976 (#16 US, #7 UK), it has gone on to become a favorite of many a Queen fan, and Veronica Deacon too, no doubt. — Johnny B
88. “Vision of Love” – Mariah Carey.
Forget about the decade of Froot Loop behavior from the porpoise-voiced diva, and focus on the amazement we all felt when Carey — all of 20, and just a diaphonous slip of a thing with a voice built for moving mountains — burst on the scene with what might have been the last great torch ballad of the 20th century. Her later recordings were built for cheap speed, but “Vision of Love” is timelessly classy. — Jeff Giles
87. “Crazy Love” – Van Morrison.
Van Morrison’s Moondance album has become standard issue for any college kid’s CD collection, and for good reason–like Bob Marley’s Legend, it’s an unstoppable parade of hits. “Crazy Love” finds the Belfast Cowboy stepping back from the jazz-infused delirium of the title track to deliver a straight-ahead message of affection, graced as all his songs are with his unforgettable vocals. It’s been covered countless times, but really, what’s the point? Who’s more definitive than Van the Man? No one, that’s who. — Springer
86. “Too Much Heaven” – Bee Gees.
A gorgeous plastic soul ballad, sung in falsetto by the kings of night fever. When I hear it, I think of the first flushes of new love, when all things are possible, when time and space are just there to serve as markers of your love affair, one that cannot help but go on forever, or beyond. Disagree? Listen again. “You’re my life,” Barry Gibb sings, his voice soaring over the orchestration, “I can see beyond tomorrow / Everything we are will never die.” Is there another time in your life when you could think, much less say, something like that? — Rob Smith
85. “Harvest Moon” – Neil Young.
Neil Young has written his share of songs about love over the years, but they were mostly written from a young man’s perspective prior to the 90’s, and were not necessarily concerned with “romance” as much as examining his feelings about the ups and downs of his relationships with Carrie Snodgress and others. 1992 found him seeking to mellow out a bit after his “difficult” Geffen period and a few years of critically-approved crashing and bashing with Crazy Horse, and the 20th anniversary of his Harvest album seemed to be as good a reason as any to do so. There’s a definite autumnal vibe to it’s sequel-in-name-only release Harvest Moon, and its title track, arguably the finest thing on the whole record, is not only a beautiful love song set to a shuffling beat (visualized in the video by an old man sweeping the floor in a bar) written for his longtime wife Peggy, but is also a genuine valentine written from the point of view of someone who’s lived life and realizes what he has, and is grateful for it. This comes across as one of the most honest songs Young has ever committed to tape, and given his history, that’s saying something. — JB
84. “Love Will Tear Us Apart” – Joy Division.
What the hell is this doing here? This is not a love song — its legacy is not festooned with flowers and devotion, but is shrouded in depression and death. Am I right? Well, tell that to the Gen-Xers who have turned Ian Curtis into perhaps the most romantic figure of the punk/new wave era — and who have attached a sort of perverse reverie to his melancholia and unfulfilled potential … and to “Love Will Tear Us Apart.” (This same generation of fans spent much of the ’80s swooning over, and chucking daisies at, a gloomy, self-proclaimed celibate like Morrissey.) In any case, Curtis was the brooding antihero that every post-punk girl wished she could have saved, and “Love Will Tear Us Apart” is the deathtrap that took him away. And you gotta admit, that’s fodder for one kick-ass unrequited-love song. — Cummings
83. “My Love” – Paul McCartney & Wings.
By 1972, in the wake of the Beatles’ breakup, Paul McCartney was creatively scuffling. 1971’s Ram was successful commercially, but was a bit of a mess. The first Wings album, Wild Life, which came later that same year, made Ram look like Abbey Road, its off-the-cuff would-be spontaneity coming across as half-baked and slapdash (but still tuneful- McCartney never lost that). Though he continued to have chart success, the likes of singles-only “Hi Hi Hi”, “Give Ireland Back to the Irish”, and “Mary Had a Little Lamb” were perceived (rightly so, but I like all three) as juvenile and shallow. Macca’s cred, as it were, was at an all-time low. So, after all this (and after a battery-charging tour of college campuses, his first since the Fab days), the smooth, polished, produced-to-a-tee “My Love” took everyone by surprise- here at last was a callback to McCartney the balladeer, the shot caller, the Beatle Magic Man, and the song went straight to #1 in the U.S. and #9 in the U.K. Written of course as an ode to his Lovely Linda, it sounded so earnest, suave, and dreamy that it was easy to ignore how simplistic the lyrics were- its moon-June-spoonish rhyme scheme and reliance on whoa-ohs instead of actual, you know, words, were a sign that Paulie had only partially regained his Fab mojo, as a look at the subsequent Red Rose Speedway lyric sheet would bear out. But hey- it does conjure up a potent romantic vibe with its lush, echoey strings, and former Grease Band guitarist Henry McCullough’s tasteful solo (Macca had written it out, but Henry asked if he could do a take his way- Paul wisely used the new take) is as good as any that can be found on any other McCartney solo recording. — Johnny B
82. “Sweet Love” – Anita Baker.
Here’s an impeccable example of the type of classy grown folks’ music that we used to leave room for on the Top 40 — and damn, what a pedigree: Baker co-wrote “Sweet Love” with prolific session bassist/Brothers Johnson member Louis Johnson, a.k.a. “Thunder Thumbs,” and Earth, Wind & Fire saxophonist Gary Bias. And there, on top of that effortlessly sexy arrangement, is that Voice. “Sweet Love” is hold music now, but don’t be fooled — this is a classic baby-maker of the highest order. — Giles
81. “The Book of Love” – The Magnetic Fields.
“The book of love is long and boring,” sighs Stephin Merritt. “No one can lift the damn thing.” Such wit and candor is rare in pop songs, and Magnetic Fields’ 69 Love Songs (of which “The Book of Love” is one) is brimming with Merritt’s refreshingly honest slant on the oldest and greatest of popular song subject matter. Merritt’s peculiar brilliance lies in his way of warping genre conventions without breaking or ridiculing them — he’s an affectionate ironist, and “The Book of Love” embodies that as well as any song on that sprawling collection. The book of love that he describes is tedious and “filled with things we’re all too young to know,” just as a real, comprehensive tome on love would be. But Merritt knows love is not all facts and figures, and the affectionate choruses mean just what they say: “But I/I love it when you sing to me/And you/You can sing me anything.” — Dan Wiencek
80. “Crush” – Dave Matthews Band.
Dave Matthews writes songs about God, death, and sex with the reckless aplomb of a stunt pilot, but where he really shines are the times where he hones in on matters of the heart. “Crush” is, without pretense, a song to celebrate the love he has for his wife. Firmly rooted by Stefan Lessard’s bouncy bass line, Matthews’ tenor plays in the pocket, building with each verse. — Parr
79. “I’ve Been Loving You Too Long To Stop Now” – Otis Redding.
Love is pain sometimes. It gets inside of you, makes you sick, seizes your brain, wrings your heart out, and the cruelest card in the deck is that we shuffled it ourselves and added the joker in. There have been millions of “Baby, please don’t go” kinds of songs (including K.C. and the Sunshine Band’s “Baby Please Don’t Go”), but you never truly felt it like you feel it from Otis Redding. Here is a guy who, at some point or another in what would wind up a desperately short life, knew real pain over having that lover leave, and having no ability to escape that connection. It’s not obsession; that’s way too easy. Obsession is all touch and no feel. “I’ve Been Loving You Too Long To Stop Now” is all about the heart, the veins, the soul. The song is coming from somewhere way down deep, and as you find from only the best performers, you not only feel Otis’ pain but your own. The song makes you not mates of misery but mates of soul. — Dw. Dunphy
78. “Moving Pictures, Silent Films” – Great Lake Swimmers.
On its surface, “Moving Pictures, Silent Films” is a simple song about hibernation. When we burrow deeper for meaning, it seems as though it has much more to do with waiting. At times in our lives, many of us tuck ourselves into an emotional cocoon, where our heart beats “slower and slower,” until something – someone brings us to life again. Songs that are written in 3/4 time are comparatively rare, but this one is achingly beautiful. It’s the perfect song for the first waltz at a wedding. — Zack Dennis
77. “Hallelujah I Love Her So” – Ray Charles.
Everyone from Hugh Laurie to Crystal Gayle has covered this song, and for good reason: Sad or romantic love songs are a dime a dozen, but it’s tricky to capture the joyous excitement that a good relationship can bring, and “Hallelujah” manages it better than most. — Giles
76. “Crazy for You” – Madonna.
The first single released from the soundtrack of the 1985 film Vision Quest, ”Crazy For You” was Madonna’s first ballad and is probably one of her most enduring. It was a huge hit for her, becoming her second number one on the Billboard Hot 100 and netting Her Madgesty her first Grammy nomination. Written by John Bettis and Jon Lind, its lyrics tell the tale of the first meeting at a night club of the film’s main characters, played by Matthew Modine and Linda Fiorentino. (Madonna also appeared in the film performing the song at a night club and is credited as ”Singer at Club.”) ”Crazy for You” was a little more sophisticated and demure than her work up until then, and it was important to her to prove that she could do more than just dance-pop. The song’s crossover appeal introduced her to legions of new fans, as it also charted on the Adult Contemporary and R&B charts. It was also the song my aunt and uncle danced to at their wedding in the late 80s, which I thought, at the time, was the coolest thing ever. — Kelly Stitzel
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