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21 of the Greatest Swing Songs of All Time

Last updated on March 14th, 2019

A selection of famous swing songs guaranteed to get you moving

Swing – a style of music so firmly rooted in the 1930s that the very sound is synonymous with unemployment, poverty, and the rise of history’s most infamous political leaders. Yet, in spite of the horrors which plagued that long-suffering decade, the music that defined it has a profoundly enduring quality – its focus on mood-lifting rhythm and danceability was a beacon in a dark time; proof that with the right melody, we can pull through the very worst the world can throw at us.

The heyday of the swing band took place between 1935 and 1946, but it’s impossible to confine the broad influence of swing to the soundtrack of the 20th century’s most notorious years. The leaders of swing in that time have influenced a pool of musicians from their contemporaries to modern pop stars – so travel with us through the last century as we discover some of the top swing songs, while trying to answer the question: what makes swing songs “swing”?

The Origins of Swing – Folk Take Notice!

1. Shanghai Shuffle – Fletcher Henderson

Fletcher Henderson is the man responsible for the origins of swing in the big band decade, the “Roaring Twenties”.

One of the most influential arrangers and bandleaders in jazz, it was Henderson who crafted the recipe for swing. Benny Goodman, playing on NBC radio, needed fresh charts every week – and Henderson was the man who provided them.

The Shanghai Shuffle is a great demonstration of the difference Louis Armstrong made on his arrival to the group, and shows us the importance of each individual musician in making famous swing band songs.

2. At the Dark Town Strutter’s Ball – Benny Goodman

Benny Goodman is one of the great swing musicians and is regularly credited as having launched the swing era. Dancers loved the new rambunctious style and rhythm of his arrangements at the Palomar Ballroom in 1935. The “hot” swing style launched him into immediate fame, inspiring admirers and imitators nationwide, transforming the landscape of American music.

3. It Don’t Mean a Thing (if it Ain’t Got That Swing) – Duke Ellington and Ivie Anderson

Credited as being the first popular tune with the word “swing” in the title! One of the classic swing songs, it became, according to Ellington, an “expression of a sentiment which prevailed among jazz musicians at the time”. If you want a swing song to sum up the jazz and swing penchant of the era, then this is the one – a jazz standard inducted into the Grammy Hall of Fame in 2008, it’s hard to find a more legendary piece.

Swing at its Height – Everybody’s Dancing!

4. South Rampart Street Parade – Bob Crosby and the Bobcats

By the mid to late thirties, the popularity of swing was at its peak, and the swing bands were at the height of their power. Yet, the Crosby band managed to combine the popular swing style with elements of older jazz – giving them an inimitable sound and style.

Their unrepentant determination to eschew popular trends by playing older jazz standards in their own style, yet within the big band swing context, meant the Bob-Cats would outlast their contemporaries, playing well into the 1970s and known by many as “The World’s Greatest Jazzband”. “South Rampart Street Parade” was their biggest hit.

5. In the Mood – Glenn Miller and his Orchestra

This number one hit by iconic bandleader Glenn Miller is possibly the most recognisable swing tune the world over. It topped the charts for 13 straight weeks in the U.S. and in 1983 was inducted into the Grammy Hall of Fame. In 2004 it was inducted into the Library of Congress National Recording Registry for recordings that are “culturally, historically, or aesthetically significant”. And the controversy over its similarity to Wingy Manone’s “Tar Paper Stomp” just goes to show that Picasso was right – “lesser artists borrow; great artists steal”.

6. Sing, Sing, Sing (with a Swing) – Benny Goodman

If there was one song on this list that could rival “In the Mood” for its distinctness and ease of recognition, this would be it. Big band swing isn’t defined much better than this piece. The longest live recording (with impromptu solos) of “Sing, Sing, Sing” took over twelve minutes, while the Goodman recording in 1937 lasted just short of nine minutes, taking up both sides of a 12-inch 78rpm record.

Goodman recalls how big Sing, Sing, Sing was when they began performing it on their second trip to the Palomar in 1936, and that “no one-nighter was complete without it”. The orchestra played the song in the 1938 film “Hollywood Hotel” and it has remained an evocative staple of the swing and big band era ever since.

7. Don’t Sit Under the Apple Tree – The Andrews Sisters

As the world marched into yet another global conflict, music was there to lift spirits. In 1939, a song based on a 19th century English folk piece called “Long Long Ago” debuted on Broadway. It was called Yokel Boy, and when the USA entered the war in 1941, the lyrics were changed to the now legendary hit. From 1942 to 1943, “Don’t Sit Under the Apple Tree”, a story of lovers separated by war, occupied first place in Your Hit Parade, the longest period for a war song to hold first place.

While there were three different version of the song on the radio Hit Parade at the same time, with recordings also by Kay Kyser and The Modernaires, the Andrews Sisters were the ones who made it truly famous – they recorded with Glenn Miller, Decca Records, and sang it for a memorable movie scene in “Private Buckaroo” with the Harry James Orchestra.

The Downfall of Swing – Soldiering On

8. Chattanooga Choo Choo – Glenn Miller

It seems only right that a man who achieved 23 number one hits in four years (that’s more than Elvis Presley or the Beatles achieved in their careers, by the way) would appear more than once on this list.

By the time the USA had entered the war in 1941, the downfall of swing had already begun, and despite the fabulous music still being churned out by bandleaders like Glenn Miller, royalty conflicts with broadcasters, wartime travel restrictions, military drafting, and a ban on recording by the American Federation of Musicians meant vocalists (who were rising in popularity with smaller bands) were rapidly on their way to replacing the traditional orchestras.

When Miller’s aeroplane disappeared over the English Channel in 1944, the world was robbed of one of swing’s leading lights, and the decline seemed ever more inevitable. “Chattanooga Choo Choo” – part of the soundtrack for “Sun Valley Serenade” – remains one of Miller’s greatest contributions to music. It was the first song to receive a gold record, for sales of 1.2 million copies, in 1942.

9. We’ll Meet Again – Benny Goodman and Peggy Lee

Peggy Lee signed on to sing with Benny Goodman during a time when vocal harmonies were soon outshining their big band accompaniments. In 1939 Vera Lynn made “We’ll Meet Again” famous, giving its name to the eponymous 1943 musical in which she played the lead role. But the year before, Goodman recorded the track with Peggy Lee, using his trademark swing style.

By the mid 40s, the popularity of big band orchestras had plunged, and swing had fallen out of favour with jazz musicians by the end of the decade. Goodman had warmed somewhat to bebop in the 40s, but it had lost his approval by the 1950s. Despite some success, his attempts to return to what he did best – swing – never truly materialised.

The epoch of big band swing was over, and though he was inducted into the Down Beat Jazz Hall of Fame in 1957, his attempts to tour with a new band was a disaster. He soldiered on however, playing in small clubs until his death in the 1980s.

Swing Revival – Bringing Swing to the Modern Age

10. Pachuco – Royal Crown Review

Formed in Los Angeles in 1989, Royal Crown Revue (RCR) are credited with starting swing revival – bringing back traditional orchestral swing arrangements near the turn of the century. It was a move that inspired the formation of other groups like the George Gee Orchestra and Lavay Smith’s Red Hot Skillet Lickers.

“Pachuco” was recorded as part of the soundtrack for 1994 movie “The Mask”, which helped to cement Jim Carrey’s significance as a comedy tour-de-force in the 1990s, and put RCR on the road to numerous other film and television appearances, including “Golden Gate” and “Buffy the Vampire Slayer”.

They even backed Bette Midler on her 2003-2004 Kiss My Brass tour, with Trumpeter Scott Steen as the featured soloist.

11. Diga Diga Doo – Big Bad Voodoo Daddy

Big Bad Voodoo Daddy are a contemporary group that are guaranteed to take listeners back to the 1940s, having concentrated on playing swing revival in clubs and lounges in their early years. After playing punk and alternative rock in the 1980s, band founders Scotty Morris and Kurt Sodergren launched two CDs under their own label before getting their break with a feature in the comedy-drama “Swingers” in 1996. A record deal with Interscope and countless live performances have followed, and Big Bad Voodoo Daddy are firmly established as pioneers at the forefront of swing revival.

12. Peroxide Swing – Michael Bublé

Before Bublé had become a household name, then came “Totally Bublé” – an EP recorded in 2001, but released in 2003, following the success of his self-titled third album.

Funnily enough, it was the classic track “Mack the Knife”, a swing hit for Louis Armstrong and Bobby Darin, which launched Bublé’s career, proving yet again the power of the genre to win over audiences.

Bublé’s inspirations and appreciation for the likes of Ella Fitzgerald and Frank Sinatra shine through in Peroxide Swing. Mixed with the youthfulness of a modern pop artist, the classic swing elements are revived in a way that feels fresh yet familiar.

13. My Baby Just Cares for Me – George Michael

This classic jazz standard was written for the film version of the musical comedy “Whoopee!” In 1930, but most will remember Nina Simone’s 1958 recording which became a top ten hit in the UK after its use in a perfume ad.

George Michael recorded his version in 1999, including it on the album “Songs from the Last Century” – a recording mostly consisting of old jazz standards. Shania Twain beat him to the top spot, Michael’s album peaking at number two instead, but that does little to harm the perfect combination of smooth swing era backing track and Michael’s contemporary vocal style.

British Dance and Swing – Enduring the Years

14. Midnight, the Stars and You – Al Bowlly with Ray Noble and his Orchestra

Not particularly popular at the time of its introduction, “Midnight” became an iconic recording for Al Bowlly after Kubrick selected it for his ballroom playlist in the 1980 horror movie “The Shining”.

On a visit to the United States following his touring success in Britain, Glen Miller put Bowlly at the head of a hand-picked orchestra beside Ray Noble where he saw great success. His popularity declined in Britain during his absence, however, and he had a rocky career when he returned home, marred by health problems and financial difficulty.

Bowally’s trademark “crooning” – a soft, expressive style of singing – combined with the Glen Miller big band swing influence, helped to make his music distinctive to anything else of the time, and has been imitated ever since. While most recordings of “Midnight” published online now have “Ballroomesque” reverberations added (for that haunted, Shining effect, of course!) we’ve managed to find an unmolested version for you to enjoy.

15. It’s a Hap-Hap-Happy Day – Arthur Askey

A record that’s sure to add some sunshine to your day, this wartime favourite typifies the style of British swing and dance music that had been so popular during the Golden Age of British music – combining the American origins of jazz and big band but with a characteristic British sense of melody and good-time rhythm carried over from the traditional music halls.

Comedians of the day would sing backed by British dance-band leaders, and “Happy Day” is a favourite, having featured in “Gulliver’s Travels”. It firmly evokes a sense of novelty over energetic dance music. Thanks to British copyright laws, and the continuing ballroom tradition, British swing and dance music lives on, surviving far better than the US styles of the same period.

Themed Swing Songs – Swing for All Occasions!

16. Dream a Little Dream – Robbie Williams (Festive Swing)

We’ve proven that swing isn’t confined to the 1930s, and Robbie Williams showed it further by reviving this classic number in 2005 (which has been recorded by more than 40 artists!) for modern audiences.

We know this isn’t from a dedicated Christmas swing songs album, but we simply love the festive nostalgia recreated in the video’s Dean-Martin-show-style special effects, so it had to take the spot. In using crooner vocals to deliver a handful of uptempo favourites and ballads alongside big band symphonic arrangements in the album “Swings Both Ways”, Williams’ second Swing album is a must-listen for fans of both Williams and the genre.

17. The Way You Look Tonight – Frank Sinatra (Wedding/First Dance Swing)

Few artists have endured in popularity like Frank Sinatra, and combining a standard from any genre to such an iconic figure of music seems only to be a recipe for success. “The Way You Look Tonight” continues to be a phenomenally popular first dance choice, even for those not looking specifically for wedding swing songs. We feel Frank’s distinctive personality carries through into his voice, and that’s what makes it such a great choice for newlyweds.

18. Beyond the Sea – Robbie Williams (Romantic Swing)

It took just one word to change Charles Trenet’s rather popular chanson classic to a hit contemporary love song – From “La Mer” (The Sea), came “Beyond the Sea”: the start that Jack Lawrence needed to finally make the song famous.

Bobby Darin’s version is the most well-known, of that we have no doubt, but we particularly enjoy Robbie Williams’ charismatic take. From “Swing When You’re Winning”, the song gained particular exposure by being used on Disney Pixar’s Finding Nemo, which is sure to make any Disney Fans favour this one when it comes to browsing romantic swing songs to woo your beloved!

19. Jumpin’ Jive – Cab Calloway and his Orchestra (Musical Swing)

Some twenty musical numbers were crammed into the 77 minute runtime of “Stormy Weather”, the masterfully made 1943 Hollywood musical that follows the tale of Bill Williamson, a dancer returning from the Great War to pursue a career as a performer. And while any of them could make this flick worthy of our favourite swing musical, what truly makes it special is the “Jumpin’ Jive” – a swing score performed by Cab Calloway and his Orchestra, thoroughly enhanced by what is possibly the greatest example of virtuoso footwork by the Nicholas brothers.

20. Mack the Knife – Westlife (Party Swing)

Bobby Darin achieved a great deal of chart success with “Beyond the Sea”, but it was Mack the Knife which took him to number one. Darin’s is, without doubt, the definitive version of this song, acknowledged even by Frank Sinatra. At its heart, the song tells the story of a cold-blooded murderer and bourgeoisie hypocrisy, first performed at The Threepenny Opera in late 20s Berlin.

Westlife’s Rat Pack tribute, “…Allow Us to Be Frank” achieved good success following Brian McFadden’s departure, and isn’t a patch on the original Rat Pack, obviously. But, there’s plenty of swinging, crooning, and fabulous big band action with their 60-piece orchestra to introduce a younger generation to the pop of days gone by and get the party moving.

21. I Wan’na Be Like You – Louis Prima (movie swing)

We end our list on a high with the King of the Swingers himself. Featured in “The Jungle Book” and written by brothers Robert and Richard Sherman, “I Wan’na Be Like You” is one of Disney’s most enduring songs. The song has since been rerecorded on numerous occasions, including by – you guessed it – Robbie Williams. It’s not surprising that this of all swing songs has such lasting appeal: as Baloo says, “well, man, what a beat!”.

Swing – Not Just a 30s Thing!

We hope this list has proven to anyone reading that swing may be rooted in the past, but its influence has permeated music right up to the modern day. We’re sure it will endure long beyond our lifetimes, too. We’ve just scratched the surface when it comes to covering all the genres that swing has influenced – bebop jazz, jump blues, swingin’ pop, and cross-genre western swing all deserve posts of their own! But we hope this little waltz (or should that be Jitterbug?) through history has taught you something about the genre, the people involved, and at the very least got your feet tapping! If we’ve missed off any of your favourites which you think we should know about, be sure to get in touch!

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