50s

My Top 10 Doo-Wop Songs

April 20, 2026 — Leave a comment

No music captures the yearning feeling of a tender heart quite like doo-wop. In its purest distillation there are only vocals, blending strong harmonies and bittersweet melodies to tell tales of love and heartbreak. Pioneered by young Black men in the 1940s, doo-wop songs became pop hits in the early 50s and went on to influence the DNA of contemporary R&B music. The golden age of doo-wop skirts the end of the singles era and the beginning of full-length albums in American music. The Flamingos, Chantels, and more put out great LPs, but doo-wop is largely a singles genre. So after a month or so steeped in doo-wop classics, I present my top 10 doo-wop songs of all-time. Youtube links are under each song and a Spotify playlist of all these songs and more is at the end.

10. Lee Andrews & The Hearts – “Long Lonely Nights” (1957)

Questlove’s father Lee Andrews fronted The Hearts, a doo-wop quintet in Philadelphia who recorded this classic, written by Andrews himself. Its circular melody is indicative of classic doo-wop, and the piano accompaniment (with a notable two-note highlight in the bridge) perfects the composition.

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9. The Chantels – “Maybe” (1957)

The song that inspired Ronnie Spector to sing. “Maybe” is shot out of a cannon, with classically trained lead Arlene Smith piping the vocals down from heaven. Its heavenly sound is further cemented by it being recorded in a midtown Manhattan church. Love-blind desperation is a recurring theme in doo-wop, but rarely has a singer sounded so in need of their beloved. Her love returns, of course, but only in dreams.

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8. The Moonglows – “Sincerely” (1954)

What sounded like a fairly standard, mellow doo-wop tune really surprised me during the chorus. Lead singer Bobby Lester’s vocals flutter way up high during the delivery of “why I lo-o-ove that girlie so,” before the whole group creates a sharp wall of sound behind “never let her go” It’s a truly striking moment that makes “Sincerely” one of my standout doo-wop songs. I find myself blaring this one in the car.

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7. The Jive Five – “My True Story” (1961)

One of the more dramatic entries in doo-wop, with lead Eugene Pitt hitting a heart-piercing falsetto on the repeated “cry, cry, cry” chorus. The narrative is a bit muddled (some kind of love triangle?), but what matters is the pain that comes through.

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6. Danny & The Memories – “Can’t Help Lovin’ That Girl (of Mine)” (1964)

My most esoteric choice on this list, Danny & The Memories were an early incarnation of the group that became Crazy Horse. Before backing Neil Young, they recorded a few doo-wop tracks in the early 60s. I’ve been listening to their version of “Can’t Help Lovin’ Dat Man” (from the Kern and Hammerstein musical Show Boat) for years, and I can’t shake how good it is. Their doo-wop vocals are pitch-perfect, and the melody is timeless.

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5. The Chords – “Sh-Boom” (1954)

Perhaps the happiest of the tracks on this list, “Sh-Boom” looks hopefully toward the future rather than wistfully toward the past. The first verse turns from English to gleeful vocalese (“boom they-lama-be-ding-dong…”), as though normal words couldn’t express the joy of love. This scat-singing was further explored by The Chords in their single “Zippity-Zum” (lyrics include “wee-bop and a skippity-hop”), but that record failed to chart the way “Sh-Boom” did. “Sh-Boom” reached top 10 on the pop charts, proving the infectious possibilities of doo-wop. Sh-boom!

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4. The Harptones – “My Memories of You” (1954)

Sweetly crushing and deceptively simple, this Harptones tune begins a capella and softly mixes in bass, guitar, and organ to accompany some of the strongest doo-wop harmony I have heard. The refrain “Knowing that I love you how could you break my heart?”, (with a touching vocal lift on “that”) kills me every time. This track is addictively good.

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3. The Flamingos – “I Only Have Eyes For You” (1959)

Uniquely mystical, hypnotizing, brilliant… there are hardly enough superlatives you can lay on this canon classic. The rapid “do-bop shoo-bop” vocals remain one of the most iconic doo-wop vocalizations. What I learned only recently is that this song was written decades before The Flamingos’ recording. The 1934 Busby Berkeley musical comedy Dames features the first recording, with a sappy and upbeat, almost comedic tone.

The Flamingos version, however, slows the pace down to a spacious waltz. The echo-laden recording adds a haunting effect, further cemented by the group recording it on October 31, 1958. This song’s late-night atmosphere is unmatched.

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2. Little Anthony & The Imperials – “Tears on My Pillow” (1958)

“Little” Anthony Gourdine was 17 when The Imperials recorded their first single, “Tears on My Pillow”. His uniquely high-pitched vocals make the song an instant head-turner, and the background vocals create a heavenly atmosphere. This song contains perhaps the most heartbreaking and poetic verse in doo-wop: “If we could start anew, / I wouldn’t hesitate / I’d gladly take you back / and tempt the hand of fate” Key doo-wop themes of time, desire, and a kind of doomed unlimited devotion all summed up in a single stanza. The aching “oh-whoa-oh…” outro adds the cherry on top. Perhaps the most potent 2 minutes in doo-wop.

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1. The Five Satins – “In the Still of the Night” (1956)

Recorded in a church basement in New Haven, Connecticut, “In the Still of the Night” (originally “Nite”) is the peak doo-wop track for me. Everything about it is perfectly imperfect: the fuzzy sound quality, the yearning vocal, the saxophone solo that almost falls off beat. It’s a simple song lyrically: the narrator remembers this one night in May where he held his beloved. But for him the experience is profound, so profound that he is haunted by it. That one moment in the pre-dawn meant everything, and it always will.

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Spotify playlist of all tracks and other doo-wop favorites

Album of the Week: Ahmad Jamal’s Chamber Music of the New Jazz (1956)

June 26, 2023 — Leave a comment

Ahmad Jamal had a long and lucrative career in jazz piano, and it started off with the smooth Chamber Music of the New Jazz. Recorded in 1955 and originally released as Ahmad Jamal Plays, the album was re-released a year later (with every successive reissue known as Chamber Music). Jamal would score a hit in 1958 with his live trio album At the Pershing, recorded with bassist Israel Crosby and drummer Vernel Fournier. Chamber Music is also a trio album but without drums, instead featuring guitarist Ray Crawford (a Pittsburgh native like Jamal).

Crawford’s guitar is notable, as he plays around with little pops on “All of You” and “I Don’t Wanna Be Kissed”. Crawford’s own composition “Jeff” has always been my favorite track here, and it’s opening call-and-response between guitar and piano sticks in my head. The rest of the album is largely standards, with Jamal’s opener “New Rhumba” the exception. That track is mellow, whereas Jamal and company play with a lively flair on “I Get a Kick Out of You” (both modes are great).

The lack of drums makes for a nice late-night listen and really allows Jamal’s piano playing to stand out in all its beauty. Short and sweet, Chamber Music of the New Jazz is an easy record that nevertheless captures a magic exercise in jazz collaboration.

Listen to Chamber Music of the New Jazz here.

Album of the Week: Champion Jack Dupree’s Blues From the Gutter (1958)

July 12, 2021 — Leave a comment

“I was born in New Orleans on July 4, 1910. My father and mother were burned up in a fire when I was a kid, and I was sent to an orphanage.”

So begins the life of Champion Jack Dupree, according to the original back cover of Blues From the Gutter. A couple months ago on GSG, Jackson C. Frank told you that blues run the game, and poor Jackson dealt with a devastating fire early on in his life too. But the clearest difference between them is apparent from one glance at their album covers: Frank was a white man from New York, and Dupree was a black man from New Orleans. And it doesn’t get more Bluesy than down at the mouth of the Mississippi.

As a young man in the Depression-era South, Dupree learned piano from his mentor Willie “Drive ‘Em Down” Hall. Playing in clubs for $1.50 an hour, Dupree said he “was lucky to get [even] that”. To make ends meet, Dupree took up boxing, which is how he earned the nickname Champion. “In 1940 I fought my last match,” he said. “It was in Indianapolis and I knocked out Battling Bozo in the tenth round.” Around this time, Dupree started recording for the legendary Okeh label (they had a novelty hit in the 20s with the bizarre “OKeh Laughing Record”), before studio albums really existed.

Dupree plays deeply-rooted Blues, but one thing I really enjoy about him is his sense of humor. “Man, slow down, don’t walk so fast!” are the first words heard on Blues from the Gutter, Dupree’s first album. “Walkin’ Blues” had existed for a couple decades already, but Dupree gave it a stroll. The “Gutter” title likely comes from the inclusion of several songs about drugs. This concept wasn’t totally new, but Dupree certainly possessed a lyrical and vocal dexterity to the subject that stands out among 50s recordings. He demonstrates the two sides to the life of a drug user: “I hung around my friends that smoke reefer, I thought I was doin’ alright… But this dope is killin’ me” he sings on “Can’t Kick the Habit”. Then later, on “Junker’s Blues,” “Oh yes, I’m a junker… but I feel good all the time!”

In terms of the music, it’s tight as can be. Dupree was famously noted as a “Boogie-Woogie” pianist, but this only really comes through clearly on “Nasty Boogie”. It’s great, but I’m glad we get more hard-line blooze on most of the album. The backing band puts in work: that electric guitar on “T.B. Blues” rips, and “Bad Blood” contains a thrilling solo as well. The records wraps up with “Stack-O-Lee”, one of the most covered blues standards out (even The Grateful Dead made it a live staple for some years).

A little Google searching led me to this wonderful video of Champion Jack Dupree playing live in 1990. Starting slowly with “Bring Me Flowers While I’m Living”, the 80 year old Dupree sings with a wry smile, “I can’t use no flowers when I’m dead”. At about the 3:25 mark, none other than Allen Touissant sneaks up behind him and starts playing the piano’s highest keys. Their faces are both shining with joy. A couple minutes later, they’ve moved on to “Shake the Boogie”, and Toussaint takes over on piano while Dupree stands up to dance. Shaking his hips back and forth, he has the crowd in the palm of his hands. Sipping a beer and twinkling the keys away into a finale, the people erupt with applause. “The Champion,” Touissant says, “The Undisputed Champion.”

Listen to Blues From the Gutter on Spotify.

Album of the Week: Ray Charles & Milt Jackson’s Soul Brothers / Soul Meeting (1958)

March 8, 2021 — Leave a comment

I recently rewatched Ray (2004) on HBO, which was fun, since Jaime Foxx is so charismatic and the music is so good. I think I realized this last year watching Fassbinder’s Gods of the Plague (1970), in which the protagonist slow-dances to “Here We Go Again” in one of the best scenes. Indeed, Ray Charles was immensely talented and his discography is full of gems. In 1958 he recorded Soul Brothers with the famed jazz vibraphonist Milt Jackson, AKA Bags.

This collaboration is interesting for a few reasons. For one, there are no vocals, which makes it atypical of Ray’s output and is probably why it’s one of the lesser-known releases in his oeuvre. Additionally, the two musicians decided to play around with different instruments, switching roles occasionally. That’s Ray Charles on saxophone on “Soul Brothers” and “How Long Blues”, where Milt Jackson plays the piano.

Soul Brothers and Soul Meeting were originally released as two different albums, both culled from 1958 sessions with the latter first released in 1961. The reissue combines them and sort of jumbles the track orders: for example “Soul Brothers”, originally the first track on the titular album, is now track 8. No matter – the two albums are quite similar and the relaxed nature of the pieces don’t require much of a formal order.

As I mentioned above, Ray plays the sax here, and he rips it. I especially love “How Long Blues”. Like most of these tracks, it’s in no hurry, but once you do reach Ray’s sax playing about 6 minutes in, it’s well worth the wait. “Blue Funk” has some tight guitar playing (courtesy of Skeeter Best) and groovy vibes from Bags. You can practically smell the smoke wafting out of some southern bar 60 years ago. As a jazzy collab, this is not the most immediate Ray Charles release. But it’s perfect for that laid-back Sunday afternoon vibe.

Listen to Soul Brothers / Soul Meeting on Spotify.

Album of the Week: Frank Sinatra’s Where Are You? (1957)

November 16, 2020 — Leave a comment

Ah, Autumn. The perfect time to wistfully smoke a cigarette while staring into the ground. What’s that Frankie? You’re wondering where she is? Damn man, sorry. Haven’t seen her around. You’ll get over it, bro (probably).

I had a bit of a Sinatra phase this year. Lovely stuff, and it felt appropriate during the lonely summer months of 2020. If you ever felt like you couldn’t see your S.O. because they were in another state and it wasn’t feasible to travel during a global pandemic, or you couldn’t go to your favorite restaurant or see friends for the same reason, don’t worry! Frank understands. He’s been lonely. He’s been through it. He’ll tell you all about it.

Yes, Where Are You? is depressing, but also comforting. Stephen Thomas Erlewine of Allmusic praised its “luxurious sadness”. Want to cry diamond tears on your 24k gold pillow? This is the album for you. As soon as those first string notes open the title track, you’re wrapped up in the sad glory of traditional pop’s greatest singer.

I’ve mentioned this before, but I love music without drums. No drums! And hey, no piano either, so no percussion to be found. Standards become lullabies. But if you’re snoozing by the end of the sublime “Laura”, Sinatra bellowing “New York, NEW YORK!” at the beginning of “Lonely Town” might wake you up. No, this isn’t that New York song. In fact, most of these standards were unfamiliar to me prior to listening. The notable exceptions were also recorded by Miles Davis: “Autumn Leaves”, which Miles performed live frequently in the early 60s, and “There’s No You”, which appeared on the underrated Blue Moods.

Where Gordon Jenkins orchestrated the Where Are You? sessions, the bonus tracks (13-16) were recorded with Nelson Riddle, who conducted two of Frank’s most acclaimed works – In the Wee Small Hours and Sings for Only the Lonely. I’ve read reviews that characterize Jenkins’ arrangements as “dour” and “overwrought” compared to Riddle’s work. Frankly (heh), I can’t tell the difference. Where Are You? sounds lovely to my ears, and it’s perfect for this time of year.

Listen to Where Are You? on Spotify while smoking wistfully.