Best Bing Crosby Songs: 20 Indelible Performances From The King Of Croon

Though renowned for the warm treacly sound of his resonant baritone voice, which dominated the airwaves during the golden age of radio broadcasting in the 1930s and 40s, Bing Crosby was so much more than a singer. He was a multi-faceted entertainer who, thanks to the advent of new technological developments in the first half of the 20th century – namely the invention of the microphone together with the rise of radio and the birth of both the recording and motion picture industries – became one of the first truly international icons in the history of the world.

Besides being a prolific recording artist who sold millions of records worldwide, Crosby’s other accomplishments were many; he was an Academy Award-winning Hollywood actor who appeared in 85 movies, including seven Road To pictures with comedian Bob Hope; he was a popular radio and TV host with his own nationally broadcast shows; and, perhaps unknown to many, he was an astute businessman who played a key role in advancing recording industry technology by investing heavily in Ampex, a company which pioneered the use of magnetic recording tape after the Second World War. His other business interests contributed to the development of another technological innovation, videotape; and away from music and Hollywood, he also purchased a couple of TV stations, owned a stud farm that bred racehorses, and from 1946 up to his death in 1977, co-owned the Pittsburgh Pirates, a baseball team.

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But it is mostly for his music and movies that we fondly remember Bing Crosby today, the jug-eared, pipe-smoking entertainer who loved to relax by playing golf and was jokingly nicknamed “Old Groaner” by bandleader Tommy Dorsey. As one of pop’s first superstars, Crosby sold a phenomenal number of records – it was estimated that his sales figures had reached the 200 million mark as far back as 1960 – and during a recording career that spanned 50 years, from 1927 to 1977, he put his stamp on over 1500 songs, a feat that makes selecting the best Bing Crosby tunes a daunting task for even the most discerning and knowledgable of his fans.

Sifting through his catalog, we’ve compiled a Bing Crosby best of that is a blend of familiar and some lesser-known recordings; a combination of ice-melting Yuletide heart warmers, smoothly sung expressions of romantic joy, and indelible readings of jazz standards. What follows should be viewed as an introduction to his vast canon rather than a definitive list.

Formative years and early stardom

Baptized Harry Willis Crosby, Bing Crosby was born in Tacoma, Washington, in 1903 and raised in Spokane; one of seven children born into a devout Catholic family with Irish roots on his mother’s side. (Crosby acknowledged his Irish heritage throughout his career and in 2023, a newly compiled digital compilation, Bing Crosby’s Irish Songbook, celebrated his association with the Emerald Isle.)

The Crosby family loved music: His mother, a homemaker, was an enthusiastic singer, and his father, a bookkeeper, played mandolin and guitar, providing accompaniment for the family when they gathered to sing together on Sunday evenings. It was as a youngster, around seven years old, that Crosby acquired his nickname, “Bing,” which quickly stuck. “There was a comic strip called the Bingville Bugle in our newspapers and there was a character named Bingo in there,” Crosby explained to a BBC TV interviewer in 1965. “Somehow or another they called me Bingo and then they knocked off the ‘o’ and now I’m Bing.”

Crosby loved singing but started out as a drummer with a high school band called The Musicaladers led by Al Rinker, brother of the noted singer Mildred Bailey. Finding common ground in their mutual love of music, they became good friends and in 1925 ventured to California where they joined several revues before being recruited as a singing duo by star bandleader Paul Whiteman. With Whiteman, they traveled to New York where they hooked up with pianist/songwriter Harry Barris and formed a vocal trio, The Rhythm Boys, in 1927. Crosby soon became the star of the group and his growing popularity was exploited by Whiteman, who featured him on several hit records and in the 1929 movie, King Of Jazz. From this launchpad, Crosby would rapidly build on his early successes to become the undisputed king of the crooners, an accolade he held for 50 years.

The Christmas classics

Bing Crosby and Christmas go together like mistletoe and wine, so there’s no better place to start a journey through his back catalog than with some of his classic festive recordings. It’s largely due to his iconic version of Irving Berlin’s “White Christmas” that Crosby’s name is synonymous with the holiday season. He was the first artist to record the warmly nostalgic number back in 1941 for his own radio show and the following year sang it on the soundtrack to the 1942 movie, Holiday Inn, which he starred in with Fred Astaire. By 1969, it was estimated to have sold 30 million copies.

Another Crosby Christmas classic is his version of songwriter Meredith Wilson’s evergreen “It’s Beginning To Look A Lot Like Christmas” featuring the glistening harmonies of Jud Conlon’s Rhythmaires. He released his version a month after Perry Como’s original in November 1951 and, since then, it has become one of Crosby’s best-loved songs.

As one of the first recording artists to release a holiday-themed album (Merry Christmas, which was first issued in 1945), Crosby covered all kinds of Yuletide ditties, from joyful festive numbers like “Jingle Bells” to traditional carols such as “Silent Night.” But one of his most surprising Christmas recordings was an unexpected duet in September 1977 with rock star David Bowie for a British TV special. Crosby crooned the words to “Little Drummer Boy” while the “Thin White Duke” offered a counterpoint of “Peace On Earth.” Crosby died a month later, after which the duet was issued as a single. It was “Old Groaner’s” final hit, rising to No. 3 in the UK.

The key collaborations

Bowie was the last in a long line of Bing Crosby collaborators. On many of his early records, Crosby shared the spotlight with artists that included jazz bandleader Paul Whiteman, the Dorsey Brothers, Duke Ellington, the Mills Brothers, and singer Connee Boswell. One of his most fruitful collaborations was when he got together with The Andrews Sisters, a sassy vocal trio from Minnesota famed for their swinging boogie-woogie style. Their close harmonies helped propel “Pistol Packin’ Mama” – an infectious slice of “hillbilly honky-tonk” – into the US Top 5 in 1943. Even more commercially successful for Crosby and the Andrews siblings was “Don’t Fence Me In,” which was purportedly recorded in 30 minutes flat. It stayed on the US chart for months, peaking at No. 1 and selling over a million copies.

In the 1950s, more stellar collaborations followed – with singers such as Peggy Lee – but one that deserves a place in any Bing Crosby best of is “Gone Fishin’,” an easy-going, conversational duet with jazz singer and trumpet legend Louis Armstrong. The two, who were real-life friends, joined forces again in 1956 on the soundtrack to the movie High Society; their joyful collaboration on the swinging “Now You Has Jazz” is easily one of the highlights of the movie’s soundtrack. The film also featured another notable Crosby collaboration; with Frank Sinatra on the humorous and slightly risque “Well Did You Evah.”

Crosby also sang many times with the “First Lady of Song,” Ella Fitzgerald, but mostly on his radio shows rather than on record. Both singers are captured in top form on the playful jazz stomp “That’s A-Plenty,” which was recorded for radio in 1954 and appears on the 2023 compilation, Bing & Ella.

Bing Crosby, the songwriter

Early on in his career, Crosby proved that he had another string to his bow beside his creamy opulent croon; his 1931 US chart-topper, a pleading ballad called “At Your Command,” revealed his talent as a lyricist. Interestingly, Crosby’s singing on that record – which was rendered in an over-dramatic, quasi-operatic manner – is far removed from the relaxed baritone croon the world came to know him for.

Crosby wasn’t a prolific writer – his songwriting credits only numbered 21 – but among his major compositions was his Top 5 hit “I Don’t Stand a Ghost of a Chance With You,” which he co-wrote with noted lyricist Ned Washington and composer Victor Young, the writers behind “My Foolish Heart.” The song quickly became enshrined as a jazz standard, covered by everyone from Billie Holiday to Thelonious Monk.

Crosby also penned his 1932 hit, the graceful “Waltzing In A Dream,” with Young and Washington, which he recorded in Chicago with bandleader Isham Jones & His Orchestra; the record made No. 6 on the US pop charts.

Bing Crosby, the swinger

In the mid-1950s, a middle-aged Crosby reinvented himself briefly as a jazz swinger a la Frank Sinatra; though he lacked the Chairman of the Board’s laconic edge and streetwise swagger, Crosby nevertheless enjoyed working in a more up-to-date musical context. He teamed up with jazz pianist Buddy Cole and his trio for the 1954 album Some Fine Old Chestnuts, an above-par collection of jazz standards whose highlights included a vibrant revamp of Fats Waller’s classic tune “Honeysuckle Rose” and a positively pulsating version of Jerome Kern and Oscar Hammerstein’s “Ol’ Man River.”

In 1956, Crosby joined the newly founded jazz label Verve for a one-off big band album arranged and conducted by the 26-year-old Chicagoan Buddy Bregman. Considered by some as the singer’s best-ever long-playing record, Bing Sings Whilst Bregman Swings included outstanding treatments of “Cheek To Cheek” and “‘Deed I Do,” both songs contrasting Crosby’s characteristic laidback delivery with sizzling, heavily accented horns and drums.

The Decca chart-toppers

Between 1927 and 1948, Bing Crosby reached the top of the US pop charts an astonishing 41 times. More than 25 of his No. 1s were recorded for Decca Records, the label that played a pivotal role in establishing his global presence. Though some Crosby fans might cite 1934’s “June To January” – his first No. 1 for the label – as a milestone in the singer’s career, his recording of “Pennies From Heaven” with the George Stoll Orchestra in 1936 is guaranteed to figure in many fans’ lists of the best Bing Crosby songs. The tune, which was inducted into the Grammy Hall of Fame in 2004, spent ten weeks at the summit of the US charts, helping to cement Crosby’s status as one of pop’s early superstars.

One of Crosby’s most unusual No. 1s for Decca was the exotic slow ballad, “Sweet Leilani,” an Academy Award-winning song that the singer popularized in the 1937 movie, Waikiki Wedding. The lush, tropical-tinged track is notable for its prominent use of Hawaiian steel guitar.

Crosby also topped the US charts in 1938 with “You Must Have Been A Beautiful Baby,” a lively tune that he recorded with the orchestra of his talented younger brother Bob.

In 1944, Crosby made the first recording of a Johnny Burke-Jimmy Van Heusen tune called “Swinging On A Star” with the John Scott Trotter Orchestra providing accompaniment. Defined by an addictive chorus, the song featured in the movie Going My Way and quickly shot to the summit of the US charts. Supporting Crosby with smooth background harmonies was a young vocal quartet from Iowa called The Williams Brothers, which included the future easy-listening superstar, Andy Williams.

The best Bing Crosby songs reveal a singular performer who despite his silky, laidback style was at the cutting edge of popular music in the 1930s and 40s. In his day, he was a genuine pioneer; a groundbreaking prototype of the world-famous solo pop star that is commonplace today. His popularity went hand-in-hand with the invention of the microphone, which was first mass-produced in 1920. It was an innovation that allowed Crosby to adopt a more nuanced style instead of projecting his voice loudly in a histrionic, stylized way, like vaudevillian performers in the mold of Al Jolson. Consequently, “Old Groaner” developed a soft, conversational croon that became his hallmark and influenced several generations of singers; from Frank Sinatra and Dean Martin to Andy Williams and Harry Connick, Jr. And, as the music of the popular Canadian crooner and self-confessed Crosby fan, Michael Bublé, clearly reveals, his influence is still alive and well today.

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