By Ray d'Entremont ——Bio and Archives--September 6, 2026
United States Supreme Court Justice Potter Stewart once wrote that hard-core pornography was hard to define, stating: "But I know it when I see it.” Swing is like that. Few musicians could explain swing to a non-musician in any meaningful way, but every musician certainly knows it when he hears it. Perhaps the best word is “feel“--that bouncy effect that makes your head bob and your toes tap. Duke Ellington himself once defined “swing” as “Harlem for rhythm.”
Swagger is equally difficult to explain, yet we all recognize it . “Charisma” understates the role of will, while “cocky” suggests too much arrogance. Suffice to say this playlist features the Big Band Era and those peacocks who coolly strutted centre stage, radiating confidence, attitude and style--the entertainers who you can’t take your eyes off for some enigmatic reason. I could have provided examples from other genres. Heavy rock band Van Halen could really swing--check out songs like “I’m the One” on the 1978 debut and “Hot for Teacher” from 1984. And clearly frontman David Lee Roth had as much swagger as anybody! But I’ve stuck to those who lived through the swing era, oozed it through their pores, and wore it on their sleeves. I’ve given priority to vocal performances, so several fine instrumentals were left off. It is noteworthy that those with the swagger could usually swing as well.
Two jazz landmarks began with this song. When first recorded in the early 1930s, the “doo-ah, doo-ah” responses that later became central to scat improvisation were created by the brass section answering singer Ivie Anderson. It was also the first popular song to put the word “swing” into the public jazz vernacular, helping launch the full Swing Era a few years later. One song on a list like this should feature scat, and who better than Ella Fitzgerald? This version comes from a 1965 Ed Sullivan Show appearance. The mutual respect between Ella and Duke is palpable as the band lays a solid foundation for her improvisation. Like Sarah Vaughan, Ella used her voice as a horn. Here it is easy to believe she is declaring that without that elusive rhythmic feel, there is no meaning. The song is a jazz manifesto.
Benny didn’t write this, but he delivered what is likely the definitive version. It swings hard. The main hook is built on the military “Assembly” bugle call. This recording catches Goodman at a transitional moment. In 1934 he was still building his orchestra and reputation; the full national explosion of the Swing Era (and his coronation as the “King of Swing”) would come the following year. The track showcases tight ensemble work, high energy, and a clarinetist who could both lead and solo with authority. Goodman’s classical training as a boy gave him extraordinary technique and the ability to sight-read, setting him apart from many self-taught players of the era.
Harlem was the place to be for this music, so take the title as solid advice to head uptown. Ella Fitzgerald sings the vocal on this 1936 recording; Webb is the drummer. He had suffered spinal tuberculosis that left him small in stature with a hunched back. By the early 1930s his orchestra had become the house band at Harlem’s legendary Savoy Ballroom, where they regularly bested visiting bands in the famous “battles of the bands,” including Benny Goodman’s.
The anthem. Immediate, irresistible big-band swing that defined the times. Composition was credited to Joe Garland, though the famous riff traces back to an earlier tune recorded by one-armed trumpeter Wingy Manone. Miller bought the song, reworked the arrangement, and recorded it in New York on August 1, 1939. It became one of the biggest and most enduring hits of the Swing Era.
Tuxedo Junction was a real place in Birmingham, Alabama--a streetcar intersection and nightlife spot where Black workers changed out of work clothes into their best outfits before heading out for an evening of music and dancing. Hawkins was from there. He honed his craft in that rich rich jazz environment and took his band to New York, where they became one of the house bands at the Savoy Ballroom, alternating with Chick Webb’s orchestra. Hawkins’ version is generally regarded as hotter and more authentic than Glenn Miller’s later, more commercial recording.
When George Harrison wanted to end choruses and the last “yeah yeah yeah” on a major 6th chord, producer George Martin complained that it sounded too much like 1940s Andrews Sisters--then considered passé. But that chord did a lot to elevate “She Loves You” to a greater song and the outcome was the Beatles first #1 hit. Don Raye and Hughie Prince wrote “Boogie Woogie Bugle Boy” about a hot Chicago trumpet player drafted into the army who turns Reveille and Taps into swinging boogie-woogie for Company B. In reality the story is almost certainly pure fiction. Recorded by the Andrews Sisters, it only reached No. 6 on the charts--surprisingly low for such an enduring classic. The arrangement is economical, staying out of the way of the masterful vocal performance. The Sisters deliver a bundle of energy, precision and optimism. There is nothing corny about classic Andrews Sisters light-pop swing: romance, exact phrasing, and pure lift.
Recorded in Chicago on 17 January 1941 and written by Krupa with trumpeter Roy Eldridge, this is a showcase disguised as a vocal dance number. Irene Daye’s buoyant vocal alternates with punched brass-and-reed passages and exuberant drum replies. It swings hard, yet the real charge comes from Krupa’s dramatic instinct as much as tempo. A forceful visual performer--flying hair, chewing gum, theatrical stick work--he built tension, punctuated arrangements and made solos tell stories. Krupa helped establish the drummer as the band’s heartbeat and worked with Slingerland and Zildjian to design the modern jazz-and-rock kit configuration.
A high-energy, riff-driven instrumental composed by arranger Sy Oliver, this became one of Tommy’s signature hits. Recorded for RCA Victor in November 1944 with Buddy Rich on drums and Buddy DeFranco on clarinet, it has a bright, propulsive bounce and swings hard thanks to Oliver. Oliver’s prominent role as an African-American arranger in a major white orchestra was groundbreaking. Tommy’s near-flawless trombone breath control and no-nonsense leadership were central. As an aside, his older brother Jimmy (the nicer one) would have made a slightly longer list; their rivalry was real, sometimes physical, yet underpinned by a complicated Irish-brother mix of love, respect and competitiveness. Both succeeded, though Tommy’s popularity rose further once he hired Frank Sinatra.
Dating to 1929 and recorded by Nat King Cole in the mid-1940s, this swinging Sy Oliver arrangement is pure Rat Pack swagger. Sammy was the ultimate entertainer--singer, dancer, impressionist, actor--whose Sands shows in Las Vegas became legendary: loose, boozy, hilarious and electric. After losing an eye in a 1954 car crash he regained balance by practising dance steps in Sinatra’s pool. When he became engaged to Swedish actress May Britt in 1960 the interracial relationship brought political headaches for Sinatra, then campaigning for JFK; hate mail poured in and the campaign urged Frank to stay away from the wedding. Sammy offered to postpone it so as not to hurt Frank; Sinatra was moved to tears and later served as best man. Sammy was not merely a friend but an equal, and Frank knew it. There was never a dull moment when those two were together. Sammy lived large, loved hard and his switch was permanently “ON.”
This song always disturbed me, so it is fortunate I never heard the original 1928 German version created for Kurt Weill and Bertolt Brecht’s The Threepenny Opera, which was far more brutal and depicted the charming yet ruthless Macheath in acts of rape, child murder and arson. Marc Blitzstein’s 1954 English translation cleaned it up for American audiences while retaining the menace. Louis Armstrong’s swinging 1955–56 version introduced it to the U.S. charts and the jazz repertoire. Dick Clark advised Darin not to record it; he ignored the advice, reached No. 1 on the Billboard Hot 100 for nine weeks, won the Grammy for Record of the Year and Best New Artist, and successfully traded his teen-idol image for nightclub and swing cachet. Ahmet Ertegun later said that after the first take everyone in the studio knew it was a smash. I wasn’t surprised when Sinatra called Darin’s swaggering version the definitive one.
Dean was not the first to record this and cut it twice. The upbeat 1964 version revived his flagging career. It carries a simple philosophical message about love as the prime meaning in life. He delivers it with his charming, relaxed, slightly tipsy shrug--a nonchalance born of unmistakable Rat Pack bravado.
If one image defined “swagger,” it would be Sinatra in a soft felt fedora. As a young man, he crossed from Hoboken into Manhattan and learned to emote watching Billie Holiday in Harlem. My favourite Sinatra hits are “My Way,” “New York, New York,” “That’s Life” and “Strangers in the Night.” Paul Anka’s English adaptation improved the French original considerably. Frank was the consummate professional: musicians arrived to find him ready, so one or two takes usually sufficed. He had a reputation in some quarters as dark and demanding, yet I gained a lasting respect when I learned he told Vegas club owners that if Sammy Davis Jr. was not welcome, neither was he. Noblesse oblige? Sammy thereafter walked through the front door.
An instrumental by three legends from the album A Jazz Portrait of Frank Sinatra. Many serious musicians, classical players included, have said Peterson possessed one of the most extensive piano techniques in any genre; in jazz he had no equal, and here his playing is at its peak. Ray Brown was a bassist’s bassist. Ed Thigpen’s brushwork and light, shimmering cymbals keep everything floating--yet unobtrusive. Peterson treats the melody with respect at first, then stretches into swinging improvisation while keeping the groove front and centre. Clean, lively and sophisticated, it is the definition of swing and earns its bonus spot.
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A boy soprano, lifelong music lover, and serial starter of things, Ray has worn more hats than most people have ever owned. Music has been a constant companion.
His playlists are an eclectic mix of genres accessed by mood and time. Over the years, he variously played in mostly rock and electric blues bands, but jazz and country too, in the Runic Stones, X-Men of Note, Purple Splintered Night, Broken Vessel, Country Gold, Eddy & The Hubcaps, ORCA, Hardscratch Road 2.0, and several others. His wife of 57 years (high school sweetheart) doesn’t agree that he needs 25 guitars!