Charles Mingus wrote ‘Goodbye Pork Pie Hat’ as an elegy for the pioneering jazz saxophonist Lester Young, who died in March 1959, two months prior to the recording sessions for what would become Mingus Ah Um. A darkly elegant ballad with a lone dissonant note full of pathos and pain, it contrasts sharply with the exuberant gospel of ‘Better Git It In Your Soul’, the track which opens the album.

Mingus Ah Um was recorded across two sessions in 1959, the first on 5 May, the second on 12 May, both at Columbia 30th Street Studio in New York City. ‘Goodbye Pork Pie Hat’ comes from the second recording session. This was Mingus’s first album on Columbia Records, and when it was issued later that year on 14 September, six of its nine songs – including ‘Goodbye Pork Pie Hat’ – were edited in order to fit on the LP. These six songs were restored in 1979, with later reissues also incorporating three bonus tracks. As a result, ‘Goodbye Pork Pie Hat’ grew from 4 minutes and forty-six seconds to five minutes and forty-four seconds.

By the end of the 1950s, Mingus had well established his Jazz Workshop, a rotating group of musicians with whom he routinely composed and performed. Accompanying his double bass on Mingus Ah Um were the familiar faces of John Handy on the alto saxophone, Booker Ervin and Shafi Hadi on tenor sax, Willie Dennis and Jimmy Knepper sharing duties on the trombone, Horace Parlan on the piano, and Dannie Richmond on drums. Richmond had first played with Mingus on The Clown, released in 1957, and would remain a constant in Mingus’s music for the next twenty-one years.

Regarded as one of Charles Mingus’s best and most accessible albums, The Penguin Guide to Jazz has called Mingus Ah Um ‘an extended tribute to ancestors’. Besides from the memorial for Lester Young on ‘Goodbye Pork Pie Hat’, it features ‘Open Letter to Duke’, ‘Bird Calls’, and ‘Jelly Roll’, songs which bring to mind Duke Ellington, Charlie Parker, and Jelly Roll Morton – although in the case of ‘Bird Calls’, Mingus stated that he had tried to replicate the sounds of actual birds, rather than quote from his illustrious contemporary.

* * *

Playing the tenor saxophone and occasionally the clarinet, Young emerged as a crucial addition to Count Basie’s band shortly before its move from Kansas City to Chicago. The producer John Hammond had heard Basie’s band over short-wave radio and after a visit to Kansas City to see them perform, he invited them to Chicago in October 1936 to record four sides which were soon released on Vocalion Records – one of the cuts, ‘Boogie Woogie’, appearing on the compilation of the same name five years later in 1941 after Vocalion had been swallowed up by Columbia.

Young had previously played with Fletcher Henderson’s orchestra as the replacement for Coleman Hawkins, but these four sides in October 1936 with Count Basie were his earliest recordings. Hammond – who worked with so many major figures of twentieth century music, from Benny Goodman to Aretha Franklin to Bob Dylan – later described the session as ‘the only perfect, completely perfect recording session I’ve ever had anything to do with’.

Lester Young remained a regular fixture in Count Basie’s band for the best part of a decade, witnessing the rise of swing and Basie’s growing fame during the core years of the big band era. In July 1937, on the tenor sax alongside Herschel Evans, he recorded ‘One O’Clock Jump’, which became the theme song of the Count Basie Orchestra. And in September 1939 he put to tape perhaps his most iconic composition, the self-titular ‘Lester Leaps In’.

In 1935, John Hammond had signed Billie Holiday to Brunswick Records, attaching her to the pianist Teddy Wilson in the hope that they would turn popular standards into swing hits. After arriving in New York to play with Henderson in 1934, Young had boarded at the house of Holiday’s mother, he and Billie striking up a close friendship which would endure for the rest of their lives. By 1937, he was playing on Holiday’s pivotal Brunswick sessions, as she found her voice and developed her inimitable style of lagging gracefully and longingly behind the beat.

It was Lester Young, whose extreme shyness seemingly went hand-in-hand with an ability to conjure hip styles and turns of phrase, who named Billie Holiday ‘Lady Day’. She in turn gave him the title ‘Prez’. Recalling their early collaborations on cuts like ‘A Sailboat in the Moonlight’, when Wilson, Holiday, and Young had often arrived at the recording studio empty handed, improvising their arrangements as they played and sang, Young said of his relationship with Holiday:

‘Well, I think you can hear that on some of the old records, you know. Some time I’d sit down and listen to ’em myself, and it sound like two of the same voices, if you don’t be careful, you know, or the same mind, or something like that.’

And through their differences, Holiday always held Young’s saxophone playing in the highest regard:

‘I always felt he was the greatest, so his name had to be the greatest. I started calling him the President.’

Young was conscripted in 1944, and unlike some of the prominent white musicians who were placed in military bands, he was assigned to the regular army. Forced to forego his place in the Count Basie Orchestra, within three months he was arrested for the possession of marijuana and barbiturates, swiftly brought before a court-martial and sentenced to ten months in a detention barracks. Young never spoke about his time in the military – it has been suggested that the fact of his white common-law wife Mary at the very least exacerbated his harsh treatment – but many critics felt that his playing after the war took on a darker tone and suffered from inconsistency, while he became increasingly disposed to alcoholism.

He was still successful, joining up with the impresario Norman Granz and performing in many of the Jazz at the Philharmonic series of concerts. Through the 1950s he occasionally sat in on Basie’s live shows, released an acclaimed album in 1954 with an Oscar Peterson quartet, reunited with Teddy Wilson for The Jazz Giants ’56 and Pres and Teddy, and briefly toured with Miles Davis. But in November 1955 he was admitted to Bellevue following a nervous breakdown, and he returned to hospital two years later suffering from malnutrition.

An argument in 1951 – at a time when Holiday was beset by legal troubles and hard drugs – had resulted in Young and Holiday refusing to speak for three years, but they reconnected in 1954 at the first Newport Jazz Festival. Their last unforgettable performance together came in December 1957, televised for ‘The Sound of Jazz’, which was part of the culture-blending CBS anthology series The Seven Lively Arts. Lester was to play as Holiday sang ‘Fine and Mellow’, but according to the jazz critic Nat Hentoff, before the band took to the stage the old friends kept to opposite sides of the room.

Young looked frail and was the only horn player who sat during the performance, but after Ben Webster had played the first solo on ‘Fine and Mellow’, Hentoff remembered:

‘Lester got up, and he played the purest blues I have ever heard, and [he and Holiday] were looking at each other, their eyes were sort of interlocked, and she was sort of nodding and half-smiling. It was as if they were both remembering what had been – whatever that was. And in the control room we were all crying. When the show was over, they went their separate ways.’

In March 1959, a run of recording sessions and live performances in Paris were cut short when Young made a hasty return to New York, suffering from pain in the stomach. On the flight over he vomited blood, a result of dilated oesophageal veins caused by cirrhosis of the liver, but although he had arranged to meet with his friend Elaine Swain, he still checked in to his old hotel – The Alvin on 52nd and Broadway, just across the road from the Birdland jazz club – and resumed drinking. He died hours later, before dawn on 15 March, at the age of forty-nine years old.

Billie Holiday asked to sing at Young’s funeral, but the family of his estranged wife refused. The critic Leonard Feather recalled that after the service, Holiday told him ‘I’ll be the next one to go’. She died four months later on 17 July, just like Young from heart failure with cirrhosis of the liver the underlying cause. Her death was a shambolic affair. After arriving at Metropolitan Hospital in East Harlem at the end of May, narcotics agents had raided her room and placed her under police guard, which was only removed in the hours before she passed away. $750 was strapped to her leg in $50 bills, all that remained of her career earnings. She was forty-four.

In contrast to the urgency shown by some of his contemporaries, Young was a relaxed and fluid saxophonist, the effortless rise and fall of his melodies always sounding fresh as he elongated phrases and made innovative uses of syncopation and glissandos. The sparseness of his line would seem to set him apart from the practitioners of bebop, which became characterised by rapid changes, a faster tempo, and more complex harmonies, but artists from Charlie Parker to John Coltrane cited him as a major influence. In fact, by the late 1950s Young felt himself so copied that he complained to Luther Cloud, his psychiatrist, ‘They’re picking the bones while the body is still warm’.

Beyond music and language, in fashion too Lester Young stood apart. He was especially fond of double-breasted pinstripe suits and – while next-generation jazzmen like Dizzy Gillespie and Thelonious Monk preferred the beret – stuck resolutely to the pork pie hat, which had originated around the 1830s as headwear for women with feathers and a curled brim, before Buster Keaton popularised the item for men in a version cut short and made stiff.

Following Keaton’s success with the pork pie hat in the silent comedies of the 1920s, it regained its curled brim and some of its height and had its heyday following the Great Depression. The architect Frank Lloyd Wright wore a pork pie with an especially wide brim, curved and floppy. Then by the early 1940s the hat had become a common accessory for the zoot suit, worn by Black Americans, Filipino Americans, Italian Americans, and Mexicans, featuring a long draped jacket with padded shoulders accompanied by high-waisted, wide-legged trousers with pegged cuffs. The Zoot Suit Riots of 1943 saw mostly Mexican youths attacked in Los Angeles by American servicemen, whose accusations of unpatriotic thuggery barely masked their prevailing racism.

Like Keaton, Young made his own pork pie hats, although rather than soaking and cutting the original store-bought products, he simply rolled down their crowns and left their wide brims untouched. He revealed his method in the November 1949 issue of Our World magazine, which had been founded in 1946 by the journalist and civil rights activist John Preston Davis.

Lester Young Pork Pie Hat

* * *

Charles Mingus returned to ‘Goodbye Pork Pie Hat’ twice on record. Just four years later, on Mingus Mingus Mingus Mingus Mingus, the song reappeared under the title ‘Theme for Lester Young’, which showcased the piano playing of Jaki Byard and the alto saxophone of Eric Dolphy. And in Three or Four Shades of Blue, recorded and released in 1977 for Atlantic, reworked versions of ‘Better Git It In Your Soul’ and ‘Goodbye Pork Pie Hat’ were followed by three new compositions for large ensembles. A couple of years earlier, Mingus was still at the peak of his powers performing an extended ‘Goodbye Pork Pie Hat’ at the Montreux Jazz Festival.

Elsewhere the song has been recorded live and in the studio by the Mingus Dynasty, the Mingus Big Band, and artists from Rahsaan Roland Kirk to Jeff Beck to John McLaughlin. Recorded in collaboration with Mingus in the months before his death on 5 January 1979, the Joni Mitchell album Mingus found ‘Goodbye Pork Pie Hat’ supplemented by a set of lyrics, which begin ‘When Charlie speaks of Lester / You know someone great has gone’ before conjuring Young’s common-law wife, a history of racism, and visions of dancing children.