Top 15 Old School Pop Tunes

I’m not surprising anyone by saying the Internet is an enormous place, and throughout its digital catacombs music fans have non-stop discussions and conversations about various music genres and why they matter.  Rock, Hip-hop, and even early 20th Century Jazz have been treated to full analysis, giving their themes the full scope of intellectual discourse, but one genre has been left out of these discussions, the Pre-Rock and Roll Pop of the Fifties and early Sixties.

This era of big band crooners and campy lounge has been critically neglected for decades thanks to the rockist fascism of critics like Christgau controlling the narrative, deriding them as quaint artifacts of a bygone era. Surprisingly, the use of many of these tunes in works like Mad Men and Bioshock has rehabilitated them somewhat, even inching them towards a vintage sense of cool. Now in honor of the golf swinging Fifties Dad in all of us, here are the top 15 best classic pop tunes.

PS: All tunes are from either the Fifties or the Camelot era so modern guys who make music like this won’t be on this list, sorry Michael Buble fans.

  1. Perry Como- Bippity Boppity Boo

Perry Como is one of the biggest cheeseballs on the planet, he’s so squeaky clean cut that he makes Barry Manilow look like frickin Burzum. But this same over the top wholesomeness lent his music a squishy puppy dog heart that was hard to truly hate, so his appropriately schmaltzy cover of Cinderella‘s “Bippity Boppity Boo” is a hand in glove fit. With its peppy, string sweetened arrangement and cloying sentimentality, it recalls the Leave it To Beaver innocence the Eisenhower Era tried (very hard) to project, and it’s a perfect pop tart of a tune.

  1. Johnny Mathis – Wonderful! Wonderful!

Of any song on this list, Wonderful! Wonderful! might be the tune that best captures the Atomic Age futurism that colored Fifties culture thanks to its spacey, instrumental hook. Johnny Mathis is obviously integral to the songs success, he’s one of the best vocalists of his time but the real star of the show is the arrangement which really transports the listener into the chrome plated, “jetpacking to work” future Fifties sci-fi predicted.

  1. Dean Martin – That’s Amore

Dean Martin might be the only guy on the planet who can hang out with Frank Sinatra and still seem like the coolest guy in the room, and this same sense of gravitas helps him vocally sell this tunes laughably corny lyrics. While people may associate Dino with his brassier, Vegas type numbers, “That’s Amore”’s kitschy, faux-Italian arrangement make it the best vehicle for his relaxed vocal style. No mob video game is complete without it.

  1. Percy Faith – Theme From “A Summer Place”

The definitive soundtrack to over-romanticized, suburban bliss, “Theme From ‘A Summer Place'” might be the best pop instrumental in the history of the Billboard charts, and that includes “Wipe Out.” Similar to the previously mentioned Perry Como song, “Summer Place” is unashamedly sentimental; boasting a cloyingly sweet melody and the sappiest string section ever put to tape, and this weakness is also its strength. You’ve probably heard it in a supermarket somewhere, which doesn’t hurt it in the slightest.


  1. Jack Jones – Wives and Lovers

This is a hard song to defend, considering the lyrics portray the dated chauvinism you see in Mad Men episodes, but musically few tunes capture the bright feel of Camelot Era culture better than this one. Penned by Burt Bacharach, it bears his trademark sophistication, combining punchy horns and a posh bridge into one of the best arrangements of the early Sixties. To his credit Jack Jones is a suave vocalist (you might recognize him as the Frog from Over the Garden Wall) which helps the cringeworthy lyrics go down easier.

  1. Ella Fitzgerald – Manhattan

Take it from someone who lives in NYC; Manhattan’s an overrated mess of hipsters and tourists, but that doesn’t mean I don’t support the “idea of Manhattan”. Ella Fitzgerald’s aptly titled ode to the city captures the “myth” of the city, fabricating a bustling land of joy and opportunity, painted in the garish colors of Broadway. Fitzgerald was a vocalist without peer, and her wide-eyed delivery can make even the most cynical old codger give in to the songs rose colored vision.

  1. “Tennessee” Ernie Ford – Sixteen Tons

Probably the most cynical song on the list, “Sixteen Tons” is as dark as the coal mines described in its lyrics. Perhaps as minimalistic as 50’s pop ever got, this slice of country-blues stands in stark contrast to the more polished songs of the era. This “unrefinedness” ended up endearing it to the rockabilly’s who formed in reaction to Fifties pop, as artists like Elvis and Bo Diddley would cover this in their early years.


  1. Bobby Darin – Beyond the Sea

Let’s be honest here, you already like this song, you’ve heard it everywhere and nothing I say will really add anything to your perception of the song. I will say this, it’s the definitive Vegas Lounge Lizard tune and everything about it, from Darin’s swaggering delivery, to every burst of bombastic brass, makes this song a time capsule of its era. A true classic of Casino Kitsch, and you totally sing it every time it plays over the credits of Finding Nemo.

  1. Rosemary Clooney – Mambo Italiano

Similar to “That’s Amore,” this is another thoroughly Americanized, wannabe Italian novelty that remains hard to resist due to the sheer ridiculousness of its existence. Mambo Italiano is ridiculous, with Clooney giving perhaps the most overheated vocal performance ever set to tape. The fact that a lot of the “Italian” used is actually misspoken or actually Spanish only contributes to the sheer goofiness of the tune. It’s actually hard to believe this song was probably treated as an authentic representation of It1alian culture, but that’s the Fifties for you I guess.

  1. Frank Sinatra – Young at Heart

Similar to how “Sorry” made us take Justin Bieber seriously practically overnight, “Young at Heart” singlehandedly change the perception of Sinatra from a washed up Big Band singer into a swinging lounge crooner for the Fifties. The opening strings breath youthful enthusiasm as Sinatra gives one of his more heartfelt performances. While we can all blame Sinatra for the scourge of fedora wearing, cringeworthy alt-righters, we can all agree that he made some of the greatest pop tunes in history and this song graces those ranks.

  1. Elvis Presley – Can’t Help Falling in Love

I know I said there wouldn’t be any rock artists on this list, but this tune is so glossy that it shouldn’t be slotted anywhere near artists like Little Richard or Buddy Holly. Contrary to what John Lennon would say, this is actually one of Presley’s strongest tracks, as his deep country croon feels perfectly at home next to its brushstroke drums and swirling piano. The early rock critics may have blasted it at the time but few can argue that it’s pretty much a standard as of now.

  1. Nat King Cole – Unforgettable

Nat King Cole’s the man, it’s just an incontrovertible fact. The dude was slagged off constantly by beard stroking Jazz phonies for ditching the genre in favor of manicured pop, but he rose above the hate and made some of the most subtly beautiful tunes of the decade. Cole’s restrained, sophisticated delivery makes it the perfect film noir soundtrack for private eyes to brood to as they walk cold streets. Seriously, go to Manhattan at Nighttime in Mid-December and listen to this tune and tell me you don’t think the same thing.

  1. Skeeter Davis – The End of The World

This is the most melodramatic in history, the definitive diary entry to eschatological lost love ever read by mankind. This weepy, Camelot Era ode to a breakup is perfect in the way the best pop songs are perfect, it’s short, slick and experiences emotions on a mythic level. Its lush strings are manifested teen heartbreak and Davis’ straight-faced reading of its lyrics makes it even more irresistibly maudlin. End of The World is a bratty, childish and absolutely wonderful gem that’s used ironically in Fallout soundtracks to this day.

  1. The Lettermen – The Way You Look Tonight

This song captures an oft-ignored period of early Sixties music; when Doo-wop and close harmony R&B groups smoothed out and fully entered the pop world. For Fifties rock fans who couldn’t relate to the Mod-Pop of The Beatles and The Stones, groups like The Lettermen offered an alternative with their mellowed out take on early rock. “The Way You Look Tonight” is a spooky piece of early 60’s ephemera, distinguished by The Lettermen’s beautifully stiff and robotic harmonies. Eventually this sound would mature into the smooth Californian Yacht Rock of the 70’s, and what would we ever do without that.

  1. Vic Damone – The Street Where You Live

Perhaps the best pop song of the Fifties, it captures everything the genre and time period were about and it does so beautifully. All at once it’s grotesquely schmaltzy (not surprising since it’s a cover of a My Fair Lady song) and stunningly emotional, not to mention catchy beyond all reason. The rushing violins and Damone’s operatic vocals compete for the listener’s attention and the lyrics, about how walking down a crushes street makes the narrator feel like he’s reached literal nirvana, are sappily heart rending. It’s a Norman Rockwell masterpiece, corny beyond all reason, but so idealistically sugary that it’s impossible to not love.

Sean Romano is 21 year old who lives in New York City. He is currently studying Journalism at SUNY Purchase where he writes for The Beat, the music and culture magazine of the school. He knows more than about pop music than is probably healthy and spends most of his time listening to tunes from the 2000’s, the '80s, and the '60s.