Bing Crosby in the 1940s, sporting a pipe and tailored suit.
Bing Crosby didn’t just sing—he changed the way the world listened. With a relaxed vocal style and unmatched warmth, he brought intimacy to popular music and helped shape the entire sound of the 20th century. Whether crooning a ballad or cracking a joke on the radio, Crosby had a gift for making every performance feel personal.
He was a master of many mediums—records, radio, film, and television—and one of the first true multimedia superstars. Before Elvis swiveled his hips or Sinatra sipped his bourbon, Crosby was dominating charts and box offices with effortless charm. His innovations in microphone technique and recording helped create the modern pop vocal style.
Though widely beloved, Crosby was more than just a voice. He was a savvy businessman and a cultural force, turning his easygoing persona into a brand that spanned decades. With his signature pipe and smooth delivery, he became America’s companion through war, recovery, and the rise of mass entertainment.
Yet behind the laid-back exterior was a work ethic that never slowed. Crosby recorded over 1,600 songs, appeared in more than 70 films, and hosted countless broadcasts, setting records that stood for generations. His influence touched every genre and medium—he wasn’t just a performer, he was a blueprint.
👶 Early Life
Bing Crosby was born Harry Lillis Crosby on May 3, 1903, in Tacoma, Washington, the fourth of seven children in a working-class Irish-American family. When he was just three years old, his family relocated to Spokane, where he would spend most of his youth. It was there, in a modest household filled with music and storytelling, that Crosby’s love for performance first took root.
His nickname “Bing” came from a childhood fascination with a comic strip called The Bingville Bugle, and it stuck for life. As a boy, he was drawn to vaudeville shows, phonograph records, and any form of popular entertainment he could get his hands on. While his parents encouraged education and discipline, Bing’s mind always drifted toward the stage.
Crosby enrolled at Gonzaga University with intentions of studying law, but music gradually pulled him in another direction. He began playing drums and singing in a local band, immersing himself in jazz and developing a vocal style inspired by Louis Armstrong and Al Jolson. His smooth, baritone voice began attracting attention, and it was clear that law would never be his path.
In the mid-1920s, he joined forces with fellow musician Al Rinker, and the two set out for California to chase bigger dreams. Their act caught the attention of bandleader Paul Whiteman, one of the most influential figures in early American music—and that connection would soon launch Crosby into national fame.
Bing Crosby’s professional singing career officially took flight when he joined Paul Whiteman’s orchestra in 1926 as part of the vocal trio The Rhythm Boys, alongside Al Rinker and Harry Barris. With Whiteman dubbed the “King of Jazz,” this gave Crosby exposure on a national level. He quickly stood out with his relaxed, conversational singing style—a huge shift from the theatrical, belting tenors that dominated the era. Inspired by Louis Armstrong’s phrasing and jazz improvisation, Crosby developed a unique tone that felt more intimate and personal than anything audiences had heard before.
As recording technology improved, Crosby became one of the first vocalists to truly master the microphone. His "crooning" style—softer, smoother, and filled with nuance—was perfect for the new electronic recording systems, and it brought a fresh sound to popular music. He soon left the Rhythm Boys and went solo, signing with Brunswick Records and launching a string of hits throughout the early 1930s, including “Out of Nowhere,” “Just One More Chance,” and “I Found a Million Dollar Baby.”
By the mid-1930s, Crosby was not just a radio and record star—he was the top-selling vocalist in America. His hits included “Pennies from Heaven,” “I’m an Old Cowhand (From the Rio Grande),” and “Swinging on a Star,” the latter winning an Academy Award for Best Original Song in 1944. His voice became a constant presence on airwaves during the Great Depression and World War II, providing comfort, humor, and hope during some of the darkest times in American history.
Then came “White Christmas.” Recorded in 1942 for the film Holiday Inn, the Irving Berlin-penned song became an instant phenomenon. Crosby’s rendition, filled with warmth and melancholy, captured the longing for home that defined the wartime experience. It went on to become the best-selling single of all time, with estimated sales of over 50 million copies worldwide. More than just a seasonal hit, “White Christmas” became a cultural touchstone, firmly cementing Bing Crosby as the voice of the holidays and a permanent fixture in American musical history.
❄️ “White Christmas” was written by Irving Berlin, a Jewish composer who didn’t celebrate the holiday—yet it became the best-selling Christmas song of all time, thanks to Bing Crosby’s heartfelt rendition.
🎬 Film & Television Stardom
Bing Crosby - on Johnny Carson Tonight Show
Bing Crosby wasn’t just a voice on the radio—he became one of Hollywood’s most bankable film stars, seamlessly transitioning from the recording studio to the silver screen. His first major film success came with The Big Broadcast (1932), where he performed several musical numbers and immediately proved he had camera presence. Audiences loved his relaxed style and sly sense of humor, and studios took notice.
Throughout the 1930s and ’40s, Crosby starred in a steady stream of musical comedies and romantic dramas, often pairing with leading ladies like Carole Lombard in We're Not Dressing (1934), Mary Martin in Birth of the Blues (1941), and Dorothy Lamour in Dixie (1943). But it was his partnership with Bob Hope and Dorothy Lamour in the legendary Road to... series that turned him into a comedic film icon. Starting with Road to Singapore (1940) and continuing through hits like Road to Morocco (1942) and Road to Utopia (1945), Crosby and Hope became a beloved duo whose onscreen chemistry and improvisational humor defined buddy comedies for decades.
Crosby earned critical acclaim for his dramatic work as well. His portrayal of Father Chuck O'Malley in Going My Way (1944) won him the Academy Award for Best Actor, beating out top contenders like Barry Fitzgerald (who played opposite him in the same film) and Charles Boyer. He reprised the role in The Bells of St. Mary’s (1945), starring alongside Ingrid Bergman. The sequel was equally successful, making Crosby one of the few actors to play the same role in back-to-back Oscar-nominated performances.
In later years, he starred in beloved classics like White Christmas (1954) with Danny Kaye, Rosemary Clooney, and Vera-Ellen—a Technicolor holiday musical that built upon the success of the original song. He also appeared in High Society (1956), a glamorous remake of The Philadelphia Story, sharing the screen with Frank Sinatra, Grace Kelly, and Louis Armstrong in one of the most stylish ensemble casts of the era.
Bing Crosby, David Bowie - Peace On Earth / Little Drummer Boy
Crosby’s television work was equally impactful. Bing Crosby hosted numerous specials and variety shows throughout the 1950s and ’60s, often featuring guests like Judy Garland, Dean Martin, Perry Como, and his own sons. His annual Christmas specials became a holiday staple, especially the 1977 episode featuring a now-famous duet with David Bowie on “Peace on Earth/Little Drummer Boy”—a poignant performance that aired just weeks after Crosby’s death and left a lasting mark on pop culture.
🎬 Bing Crosby’s Road to Comedy – 7-Film Blu-ray Collection
Step into the world of fast-paced wit, exotic misadventures, and smooth crooning with this 7-film collection starring the legendary Bing Crosby alongside comic partner Bob Hope and the ever-glamorous Dorothy Lamour. From their first escapade in Singapore to their final antics in Hong Kong, this iconic series captures Crosby’s comic timing, effortless charm, and undeniable chemistry with Hope—making it essential viewing for classic film lovers.
Hope, Crosby, and Lamour deliver laughs across 7 classic adventures.
This set includes:
Road to Singapore (1940) – Crosby and Hope kick off the series with tropical mayhem
Road to Zanzibar (1941) – More jungle hijinks and sly one-liners
Road to Morocco (1942) – Featuring the unforgettable tune “Moonlight Becomes You”
Road to Utopia (1946) – Crosby at his comedic best in Alaskan gold-rush chaos
Road to Rio (1947) – Musical comedy set against samba rhythms
Road to Bali (1952) – The series' only color film with exotic charm
The Road to Hong Kong (1962) – With Joan Collins and one last hurrah for the duo
Extras include behind-the-scenes footage, wartime reels like Entertaining the Troops, vintage trailers, and rare commentaries. Whether you’re revisiting a favorite or discovering them for the first time, these films show Crosby at his most relaxed, quick-witted, and musically magnetic.
Sing, laugh, and roam the globe with Bing Crosby in this beloved collection of timeless comedy classics.
Bing Crosby’s talents weren’t confined to music and film—he was also a savvy businessman and passionate sportsman with a wide range of interests. Long before it was fashionable for entertainers to diversify, Crosby was investing, owning, and building a quiet empire behind the scenes.
He co-founded the television station KPTV in Portland, Oregon—one of the first TV stations in the Pacific Northwest. Later, he was a major investor in ABC and an early advocate for pre-recorded television, working closely with Ampex Corporation to develop high-quality magnetic tape recording for broadcast. His influence helped revolutionize the way TV shows were produced and distributed.
An avid horse racing enthusiast, Crosby co-founded the Del Mar Racetrack in California in 1937 with fellow celebrities like actor Pat O'Brien and songwriter Johnny Burke. He served as its founding president and turned opening day into a Hollywood event. Bing’s own stables produced several winning thoroughbreds, and he often rubbed shoulders with racing legends and entertainment elite alike.
Crosby also loved golf, regularly participating in the Pebble Beach Pro-Am, which he founded in 1937 as the “Crosby Clambake.” It drew celebrity players like Bob Hope, Jack Lemmon, and Clint Eastwood, as well as golf greats such as Ben Hogan and Arnold Palmer. Bing was a skilled golfer himself, with a low handicap and deep respect in the sport’s professional circles.
His sports interests didn’t end there—he was part-owner of the Pittsburgh Pirates and was famously listening to their 1960 World Series win while on a European vacation, having had a recording made of the game due to superstition. That game recording, long thought lost, was discovered decades later in Crosby’s personal wine cellar and became the only known complete footage of the historic match.
Whether owning TV stations, betting on racehorses, or teeing off with Hollywood royalty, Bing Crosby lived a full and fascinating life far beyond the stage and studio—always with charm, strategy, and a quiet competitive edge.
🎧 Bing Crosby was the first performer to pre-record his radio shows, using reel-to-reel tape. This innovation changed broadcasting forever and made him a pioneer in audio technology.
🕊️ Later Years
As the 1960s gave way to a new era in entertainment, Bing Crosby remained an enduring presence, even as musical tastes shifted. Though rock and roll dominated the charts, Crosby’s smooth voice and gentlemanly demeanor continued to resonate with loyal fans. He shifted focus to television and live performances, appearing regularly on variety shows and hosting beloved holiday specials that kept his image warm and familiar in households across America.
Crosby remained active in music, recording albums well into the 1970s, including collaborations with Count Basie and Rosemary Clooney. His later recordings often reflected a quieter, more reflective tone, embracing his role as a seasoned elder statesman of American music. He continued to tour internationally, performing across Europe and the U.S., and maintained his golf schedule with the same passion that marked his younger days.
His final years were surprisingly active. In 1977, Crosby completed a well-received concert tour of the UK and Spain, where audiences welcomed him with nostalgia and admiration. Just days after taping his final television appearance—a Christmas special with his family—Crosby collapsed and died of a heart attack on October 14, 1977, shortly after finishing a round of golf near Madrid.
He was 74 years old. News of his death prompted tributes from across the globe, with Frank Sinatra, Bob Hope, and Dean Martin all publicly mourning the loss of their friend and peer. Flags flew at half-mast in his honor, and radio stations flooded the airwaves with his timeless recordings. Even in death, Bing Crosby's voice continued to comfort and connect, just as it had for over half a century.
🏆 Legacy
Bing Crosby’s legacy is woven into the very fabric of American entertainment. He wasn’t just a star—he was the star for multiple generations. With more than half a billion records sold, he was one of the best-selling recording artists of all time. His relaxed, conversational singing style changed the way popular music sounded and paved the way for artists like Frank Sinatra, Perry Como, and Dean Martin. Without Crosby, the entire crooner era might never have existed.
He appeared in over 70 feature films and earned the Academy Award for Best Actor for Going My Way (1944), becoming the first true multimedia superstar. His Road to... movies with Bob Hope and Dorothy Lamour defined Hollywood buddy comedies, while White Christmas became a perennial holiday tradition. That single song alone, recorded in 1942, remains the best-selling single in music history—a timeless anthem of nostalgia and peace.
Crosby was also an innovator behind the scenes. He was an early champion of magnetic tape recording and a key investor in television technology, changing how audio and video were captured and broadcast. In business, he helped shape everything from radio syndication to sports media events, always one step ahead of the industry curve.
From his Hollywood Walk of Fame stars (he has three) to lifetime achievement awards from the Grammy, Emmy, and Academy communities, Bing Crosby’s accolades reflect a life spent not just entertaining, but shaping the way entertainment works. His image remains a fixture every Christmas season, his voice still heard in films, commercials, and family gatherings across the globe.
More than four decades after his passing, Bing Crosby remains what he always was—a pioneer, a voice of comfort, and an American original.
ML Lamp is the owner of Kilroy Was Here. After his 20 years of working in Las Vegas in the entertainment promotions field, Mr. Lamp retired in 2002 from his job to pursue his passion for collectibles. Now as a guest speaker and author he’s living the dream, and sharing his warmth with You.
