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.
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.
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.
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.
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.
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!
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.
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.
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.
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.
Spotify playlist of all tracks and other doo-wop favorites
good singing gum 
