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Welcome to the next installment of my 1950s Wedding series. Following my look at First Dance classics, I’m sliding into the suave sophistication of the Sands Hotel and the echo of the Brooklyn subway stations.

Welcome to a new 1950s Wedding series:

First Dance & Timeless Love Songs
Rat Pack & Classic Crooners (This issue)
Doo-Wop & Vocal Harmony (This issue)
Rock & Roll Classics
Dance Floor Hits
Country & Americana
Fun & Novelty

To me, the 1950s represent a unique intersection in music history: the smooth, tuxedo-clad elegance of the “Crooner” meeting the raw, youthful energy of the “Group Sound.” This era gave us the definitive blueprint for wedding atmosphere. Songs that can transition a room from a formal dinner to a lighthearted, finger-snapping cocktail hour.

Whether I’m looking at the effortless cool of Frank Sinatra and Dean Martin or the hauntingly beautiful street-corner “close harmony” of The Five Satins and The Platters, I find these tracks carry a distinct nostalgia. They provide that rare “multi-generational” appeal that keeps the grandparents on the floor while giving younger guests a taste of timeless style.

Table of Contents

Rat Pack & Classic Crooners - 24 songs
Doo-Wop & Vocal Harmony - 20 songs
Spotify Playlists

Rat Pack & Classic Crooners

Bobby Darin - Mack The Knife

1959 - It was composed for the 1928 German musical The Threepenny Opera. Louis Armstrong introduced the song to the American mainstream in 1955. Darin’s song spent 9 weeks at #1 on the Billboard Hot 100. It eventually won the Grammy Award for Record of the Year.

Dean Martin - I’ve Got My Love To Keep Me Warm

1959 - The song was written for the 1937 musical film On the Avenue. Many artists covered this song, including Frank Sinatra and Billie Holiday. However, Martin’s version is considered the definitive “crooner” take.

Dean Martin - Memories Are Made Of This

1955 - This was Dean Martin’s biggest hit ever. It spent five weeks at #1 on the Billboard charts and was his first-ever million-selling single. The lyrics are written like a recipe for a happy life, listing “ingredients” like one small accent of blue and a sip of honey. A perfect cake-cutting song.

Dean Martin - That’s Amore

1953 - The song was originally written for the 1953 film The Caddy, starring Dean Martin and Jerry Lewis. It was nominated for an Academy Award for Best Original Song. The track hit #2 on the Billboard charts and became his first gold record.

Dean Martin - Volare

1958 - The word “Volare” simply means “To Fly”. The original version was by Domenico Modugno. Martin’s adaptation reached #12 on the Billboard Hot 100. “Volare” is considered a more “classy” alternative to a Conga line or the Bunny Hop.

Domenico Modugno - Volare (Nel Blu Dipinto Di Blu)

1958 - The original version by Domenico Modugno made history at the very first Grammy Awards in 1959. It is still the only foreign-language recording to win both Record of the Year and Song of the Year. It is one of the few songs in history to hit #1 on the Billboard Hot 100 while being sung entirely in a foreign language.

Frank Sinatra - (Love Is) The Tender Trap

1955 - The song served as the title track for the 1955 romantic comedy The Tender Trap, starring Sinatra and Debbie Reynolds. It peaked at #7 on the Billboard charts and earned an Academy Award nomination for Best Original Song. The lyrics warn of love’s dangers only to celebrate its irresistible pull.

Frank Sinatra - Come Fly With Me

1958 - The album hit #1 on the album charts, but the song never actually hit #1 as a single. However, the track has been used in many movies, making it highly recognizable to many generations. It mentions Bombay, Peru, and Acapulco Bay - perfect for destination weddings.

Frank Sinatra - High Hopes

1959 - The song was released for the film A Hole in the Head, and won the Academy Award for Best Original Song. It was so catchy and inspiring that John F. Kennedy used a version of it with rewritten lyrics as his official campaign song for the 1960 Presidential election. The track peaked at #30 on the Billboard Hot 100.

Frank Sinatra - I Get A Kick Out Of You

1954 - The song was originally written and performed by Cole Porter in the 1930s. Sinatra actually recorded this twice, with the 1953 version being a bit more relaxed and intimate - perfect for dinner music because it’s upbeat but doesn’t overpower the conversation.

Frank Sinatra - I’ve Got You Under My Skin

1956 - The song was originally a Cole Porter song from 1936. However, Sinatra’s 1950s “swing” version completely reinvented it. The “energy shift” in the middle of this track is a great time to invite all couples onto the floor.

Frank Sinatra - Love and Marriage

1955 - The song won the first-ever Emmy Award for “Best Musical Contribution” for its appearance in Our Town. The track will be recognizable to many generations. It was the theme song for the long-running sitcom “Married... with Children”.

Frank Sinatra - My Funny Valentine

1954 - The song was written for the 1937 musical Babes in Arms. It became a popular jazz standard, appearing on over 1300 albums performed by over 600 artists. It is a slower tempo and shorter song, clocking in at 2 minutes and 35 seconds.

Frank Sinatra - You Make Me Feel So Young

1956 - The song was written for the 1946 film Three Little Girls in Blue. The lyrics are famous for comparing love to “Spring”. It was the opening song for Sinatra’s landmark 1956 album, ‘Songs for Swingin’ Lovers!’. The track was strategically placed as the first track to signal a new, high-energy era for Frank.

Louis Armstrong - A Kiss To Build A Dream On

1951 - The song was featured in the 1951 film The Strip, where Louis Armstrong performed it on screen. Additional generations will recognize the song because, in 1993, it was featured prominently in the movie Sleepless in Seattle.

Louis Armstrong - La Vie En Rose

1950 - The title translates to “Life in Pink”. While Edith Piaf made it a French icon, Louis Armstrong’s version (sung in English) is the one that truly conquered the American wedding scene. It reached #28 on the Billboard charts.

McGuire Sisters - Give Me Love

1954 - The sisters got their big break on Arthur Godfrey’s Talent Scouts in 1952. By 1954, they were staples of American television. The lyrics describe a romantic, straightforward plea for affection.

Muir Mathieson - Lola’s Theme

Mathieson’s arrangement of “Lola’s Theme” (also known as the “Theme from The Blue Angel”) adds a layer of sophisticated, European-influenced drama. EDM fans will recognize “Lola’s Theme” as the 2004 house hit by The Shapeshifters.

Nat King Cole - Unforgettable

1951 - The song reached #12 on the Billboard Singles chart. It made history again in 1991. Nat’s daughter, Natalie Cole, recorded a “virtual duet” with her father’s 1951 vocals. It swept the Grammy Awards and made “Unforgettable” one of the few songs to be a massive #1 hit in two different eras.

Peggy Lee - Fever

1958 - The song is most well-known for its sparse arrangement consisting only of a walking bassline, a drummer using fingers instead of sticks, and her own finger snaps. “Fever” earned nominations for Record of the Year and Song of the Year.

Perry Como - Magic Moments

1957 - The song features one of the most famous whistling hooks in music history. The lyrics function like a musical photo album, listing simple, happy memories like “the night we had the taffy pull” and “the time you won the silver cup”. This makes it an incredible choice for a Wedding Slideshow or a Photo Montage.

Tommy Edwards - It’s All In The Game

1951/1958 - The latter upbeat version spent six weeks at #1. It is the only #1 hit in Billboard history to be written by a U.S. Vice President - Charles Dawes (under Calvin Coolidge). Plus, Tommy Edwards made history with this track by becoming the first African American male to hit #1 on the Billboard Hot 100.

Tony Bennett - Funny Thing

1954 - The lyrics’ theme focuses on the irony of love - how things that seem small can become “unforgettable” and how love often brings both “laughter and tears”. “Funny Thing” is a hidden gem to provide a “Vintage Surprise”.

Tony Bennett - Rags To Riches

1953 - The song stayed at #1 on the Billboard charts for eight weeks. Its theme plays on the idea that being “rich” isn’t about money, but about having the person you love. The track was the opening track for the 1990 film Goodfellas.

Doo-Wop & Vocal Harmony

Dion & The Belmonts - A Teenager In Love

1959 - Dion DiMucci and his group, The Belmonts, were the kings of “Italian-American Doo-Wop” from the Bronx. It peaked at #5 on the Billboard Hot 100.

Dion & The Belmonts - I Wonder Why

1958 - The song reached #22 on the Billboard Hot 100. Dion & The Belmonts performed it on American Bandstand. Dick Clark famously credited the group for bringing a “tougher, street-wise” edge to the vocal group sound.

Frankie Lymon & The Teenagers - Why Do Fools Fall In Love

1956 - The song became one of the first songs by a “teen act” to top both the R&B and Pop charts. “Why do fools fall in love?” has become a permanent part of the romantic lexicon. For a wedding, it’s a playful, tongue-in-cheek nod to the “madness” of falling in love.

Monotones - Book Of Love

1958 - The song acts as a mini-instruction manual for romance, breaking love down into “Chapter One” through “Chapter Four”. It peaked at #5 on the pop chart and #3 on the R&B chart.

Sammy Turner - Symphony

1959 - Just like Perry Como’s “Magic Moments,” Turner’s “Symphony” features a light, melodic whistling section. The track is a “Mid-Tempo Sway”. It peaked at #82 on the Billboard Hot 100.

The Chords - Sh-Boom

1954 - The Chords’ “Sh-Boom” is widely cited by music historians as the first “Rock & Roll” record to reach the top 10. Before this track, R&B and Pop were strictly separated on the radio. When The Chords released “Sh-Boom,” it became a “crossover” sensation.

The Crests - 16 Candles

1958 - The song peaked at #2 on the Billboard Hot 100 chart. The Crests were one of the first majorly successful integrated vocal groups of the 1950 featuring African American, Puerto Rican, and Italian-American members. The track was linked to the 1984 cult classic film Sixteen Candles.

The Crew-Cuts - Sh-Boom

1954 - “Sh-Boom” is historically significant because it was one of the first “R&B” songs (the Chords) to be successfully covered by a “Pop” group (the Crew-Cuts) and reach #1 on the Billboard charts. The song was placed in PIXAR’s animated movie Cars in 2006.

The Crows - Gee

1953 - The Crows were the first R&B vocal group to record and sell over one million copies and crossover to the white pop charts - before the Crew-Cuts or even The Chords. “Gee” has a driving, rhythmic piano and a “walking” bassline that makes it a pioneer of the East Coast Swing style. It hit #2 on the R&B chart and #14 on the pop chart.

The Del-Vikings - Come Go With Me

1957 - The Del-Vikings were one of the first racially integrated groups to achieve mainstream success. They featured both Black and White members. The song was featured in the 1986 film Stand By Me. It peaked at #5 on the Billboard Pop Chart and #2 on the R&B chart.

The Diamonds - Little Darlin’

1957 - The song hit #11 on the R&B charts. It was featured in the movie American Graffiti and the TV show Happy Days. At a wedding, it’s a great “sing-along” moment.

The Elegants - Little Star

1958 - The song holds a special place in music history as one of the few Doo-Wop tracks to hit #1 on the Billboard Hot 100. The melody of “Little Star” is actually based on the classic nursery rhyme “Twinkle, Twinkle, Little Star”. This is a “One-Hit Wonder” that has staying power.

The Five Satins - In The Still of The Night

1956 - This song popularized the most iconic vocal “scat” in history. The backing vocalists repeated “shoo-doo, shoo-bee-doo” throughout the track. The song was so popular that it charted three separate times (1956, 1960, and 1961). It was also the only song to have two different versions by the same artist appear on the Billboard Hot 100 simultaneously. It moves at approximately 68 BPM, which is the perfect “heartbeat” tempo for a slow dance.

The Kalin Twins - When

1958 - Hal and Herbie Kalin were actual identical twins. The song reached #5 on the Billboard Hot 100 but #1 on the UK Singles chart. The lyrics are essentially a series of questions about the future of a relationship - it even mentions walking down the aisle.

The Moonglows - Sincerely

1954 - “Sincerely” by The Moonglows is the gold standard for 1950s “R&B-meets-Pop” ballads. It reached #1 on the Billboard R&B chart and #20 on the Billboard Juke Box chart. The McGuire Sisters released a pop cover in 1955 that went to #1 for ten weeks.

The Platters - One In A Million

1957 - “One In A Million” is a phrase every couple wants to hear on their wedding day. It sits in the “Mid-Tempo Sway” category for cocktail hours or dinner music. It provides that familiar 1950s “vibe” without being a song that guests have heard a thousand times.

The Platters - Only You

1955 - The song hit the #1 position on the Billboard R&B charts for seven weeks, and #5 on the Billboard Top 100 chart. The original 1955 recording was inducted into the Grammy Hall of Fame in 1999. You can hear it in classic films like American Graffiti (1973), Superman (1978), and even Deadpool & Wolverine (2024).

The Platters - The Great Pretender

1955 - The song became the group’s first #1 hit on both the R&B and Pop charts. The Platters were unique among 1950s vocal groups for featuring a female member, Zola Taylor. In the 1980s, Freddie Mercury of Queen famously covered it. It moves at a gentle 66 BPM, making it the “50s gold standard” for a First Dance.

The Skyliners - This I Swear

1959 - The song hit #26 on the Billboard Hot 100 and #20 on the R&B Chart. “This I Swear” makes the song feel like a musical extension of the wedding vows.

The Spaniels - Goodnight Sweetheart Goodnight

1954 - The Spaniels were the flagship group for Vee-Jay Records, one of the most important Black-owned labels in American history, from Gary, Indiana. The lyrics ”It’s three o’clock in the morning / I hate to leave you” capture a universal feeling of not wanting a perfect night to end. Thus, making it a quintessential final reception track.

Is there a song that you think should be added? Let me know!

Thanks for reading,

Matthew Campbell

Wedding MusicLetter

Spotify Playlists

🎵 1950s Rat Pack Crooners & Doo-Wop

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