Bing Crosby

In 1923, Crosby was invited to join a new band composed of high-school students a few years younger than himself. Al and Miles Rinker (brothers of singer Mildred Bailey), James Heaton, Claire Pritchard and Robert Pritchard, along with drummer Crosby, formed the Musicaladers,[5] who performed at dances both for high school students and club-goers. The group performed on Spokane radio station KHQ, but disbanded after two years.[3]^: 92–97[36] Crosby and Al Rinker obtained work at the Clemmer Theatre in Spokane (now known as the Bing Crosby Theater).

Crosby was initially a member of a vocal trio called The Three Harmony Aces with Al Rinker accompanying on piano from the pit, to entertain between the films. Crosby and Al continued at the Clemmer Theatre for several months often with three other men—Wee Georgie Crittenden, Frank McBride, and Lloyd Grinnell—and they were billed The Clemmer Trio or The Clemmer Entertainers depending who performed.[37]

In October 1925, Crosby and Rinker decided to seek fame in California. They traveled to Los Angeles, where Bailey introduced them to her show business contacts. The Fanchon and Marco Time Agency hired them for thirteen weeks for the revue The Syncopation Idea starting at the Boulevard Theater in Los Angeles and then on the Loew's circuit. They each earned $75 a week. As minor parts of The Syncopation Idea Crosby and Rinker started to develop as entertainers. They had a lively style that was popular with college students. After The Syncopation Idea closed, they worked in the Will Morrissey Music Hall Revue. They honed their skills with Morrissey. When they got a chance to present an independent act, they were spotted by a member of the Paul Whiteman organization.

Whiteman needed something different to break up his musical selections, and Crosby and Rinker filled this requirement. After less than a year in show business, they were attached to one of the biggest names.[37] Hired for $150 a week in 1926, they debuted with Whiteman on December 6 at the Tivoli Theatre in Chicago. Their first recording, in October 1926, was "I've Got the Girl" with Don Clark's Orchestra, but the Columbia-issued record was inadvertently recorded at a slow speed, which increased the singers' pitch when played at 78 rpm. Throughout his career, Crosby often credited Bailey for getting him his first important job in the entertainment business.[38]

Crosby (middle) with The Rhythm Boys in c. 1929-30

Success with Whiteman was followed by disaster when they reached New York. Whiteman considered letting them go. However, the addition of pianist and aspiring songwriter Harry Barris made the difference, and The Rhythm Boys were born. The additional voice meant they could be heard more easily in large New York theaters. Crosby gained valuable experience on tour for a year with Whiteman and performing and recording with Bix Beiderbecke, Jack Teagarden, Tommy Dorsey, Jimmy Dorsey, Eddie Lang, and Hoagy Carmichael. He matured as a performer and was in demand as a solo singer.[39]

Crosby became the star attraction of the Rhythm Boys. In 1928, he had his first number one hit, a jazz-influenced rendition of "Ol' Man River". In 1929, the Rhythm Boys appeared in the film King of Jazz with Whiteman, but Crosby's growing dissatisfaction with Whiteman led to the Rhythm Boys leaving his organization. They joined the Gus Arnheim Orchestra, performing nightly in the Coconut Grove of the Ambassador Hotel. Singing with the Arnheim Orchestra, Crosby's solos began to steal the show while the Rhythm Boys' act gradually became redundant. Harry Barris wrote several of Crosby's hits, including "At Your Command", "I Surrender Dear", and "Wrap Your Troubles in Dreams". When Mack Sennett signed Crosby to a solo film contract in 1931, a break with the Rhythm Boys became almost inevitable. Crosby married Dixie Lee in September 1930. After a threat of divorce in March 1931, he applied himself to his career.

Crosby in 1932

15 Minutes with Bing Crosby, his nationwide solo radio debut, began broadcasting on September 2, 1931.[40] The weekly broadcast made him a hit.[41] Before the end of the year, he signed with both Brunswick Records and CBS Radio. "Out of Nowhere", "Just One More Chance", "At Your Command", and "I Found a Million Dollar Baby (in a Five and Ten Cent Store)" were among the best-selling songs of 1931.[41]

Ten of the top 50 songs of 1931 included Crosby with others or as a solo act. A "Battle of the Baritones" with singer Russ Columbo proved short-lived, replaced with the slogan "Bing Was King". Crosby played the lead in a series of musical comedy short films for Mack Sennett, signed with Paramount, and starred in his first full-length film 1932's The Big Broadcast (1932), the first of 55 films in which he received top billing. He would appear in almost 80 pictures. He signed a contract with Jack Kapp's new record company, Decca, in late 1934.

His first commercial sponsor on radio was Cremo Cigars and his fame spread nationwide. After a long run in New York, he went back to Hollywood to film The Big Broadcast. His appearances, records, and radio work substantially increased his impact. The success of his first film brought him a contract with Paramount, and he began a pattern of making three films a year. He led his radio show for Woodbury Soap for two seasons while his live appearances dwindled. His records produced hits during the Depression when sales were down. Audio engineer Steve Hoffman stated, "By the way, Bing actually saved the record business in 1934 when he agreed to support Decca founder Jack Kapp's crazy idea of lowering the price of singles from a dollar to 35 cents and getting a royalty for records sold instead of a flat fee. Bing's name and his artistry saved the recording industry. All the other artists signed to Decca after Bing did. Without him, Jack Kapp wouldn't have had a chance in hell of making Decca work and the Great Depression would have wiped out phonograph records for good."[42]

His social life was frantic. His first son Gary was born in 1933 with twin boys following in 1934. By 1936, he replaced his former boss, Paul Whiteman, as host of the weekly NBC radio program Kraft Music Hall, where he remained for the next ten years. "Where the Blue of the Night (Meets the Gold of the Day)", with his trademark whistling, became his theme song and signature tune.

Crosby's vocal style helped take popular singing beyond the "belting" associated with Al Jolson and Billy Murray, who had been obligated to reach the back seats in New York theaters without the aid of a microphone. As music critic Henry Pleasants noted in The Great American Popular Singers, something new had entered American music, a style that might be called "singing in American" with conversational ease. This new sound led to the popular epithet crooner.

Crosby admired Louis Armstrong for his musical ability, and the trumpet maestro was a formative influence on Crosby's singing style. When the two met, they became friends. In 1936, Crosby exercised an option in his Paramount contract to regularly star in an out-of-house film. Signing an agreement with Columbia for a single motion picture, Crosby wanted Armstrong to appear in a screen adaptation of The Peacock Feather that eventually became Pennies from Heaven. Crosby asked Harry Cohn, but Cohn had no desire to pay for the flight or to meet Armstrong's "crude, mob-linked but devoted manager, Joe Glaser". Crosby threatened to leave the film and refused to discuss the matter. Cohn gave in; Armstrong's musical scenes and comic dialogue extended his influence to the silver screen, creating more opportunities for him and other African Americans to appear in future films. Crosby also ensured behind the scenes that Armstrong received equal billing with his white co-stars. Armstrong appreciated Crosby's progressive attitudes on race, and often expressed gratitude for the role in later years.[43]

During World War II, Crosby made live appearances before American troops who had been fighting in the European Theater. He learned how to pronounce German from written scripts and read propaganda broadcasts intended for German forces. The nickname "Der Bingle" was common among Crosby's German listeners and came to be used by his English-speaking fans. In a poll of U.S. troops at the close of World War II, Crosby topped the list as the person who had done the most for G.I. morale, ahead of President Franklin D. Roosevelt, General Dwight Eisenhower, and Bob Hope.

The June 18, 1945, issue of Life magazine stated, "America's number one star, Bing Crosby, has won more fans, made more money than any entertainer in history. Today he is a kind of national institution."[44] "In all, 60,000,000 Crosby discs have been marketed since he made his first record in 1931. His biggest best seller is "White Christmas" 2,000,000 impressions of which have been sold in the U.S. and 250,000 in Great Britain."[44] "Nine out of ten singers and bandleaders listen to Crosby's broadcasts each Thursday night and follow his lead. The day after he sings a song over the air—any song—some 50,000 copies of it are sold throughout the U.S. Time and again Crosby has taken some new or unknown ballad, has given it what is known in trade circles as the 'big goose' and made it a hit single-handed and overnight... Precisely what the future holds for Crosby neither his family nor his friends can conjecture. He has achieved greater popularity, made more money, attracted vaster audiences than any other entertainer in history. And his star is still in the ascendant. His contract with Decca runs until 1955. His contract with Paramount runs until 1954. Records which he made ten years ago are selling better than ever before. The nation's appetite for Crosby's voice and personality appears insatiable. To soldiers overseas and to foreigners he has become a kind of symbol of America, of the amiable, humorous citizen of a free land. Crosby, however, seldom bothers to contemplate his future. For one thing, he enjoys hearing himself sing, and if ever a day should dawn when the public wearies of him, he will complacently go right on singing—to himself."[44][45]

White Christmas (1954)

The biggest hit song of Crosby's career was his recording of Irving Berlin's "White Christmas", which he introduced on a Christmas Day radio broadcast in 1941. A copy of the recording from the radio program is owned by the estate of Bing Crosby and was loaned to CBS Sunday Morning for their December 25, 2011, program. The song appeared in his films Holiday Inn (1942), and—a decade later—in White Christmas (1954). His record hit the charts on October 3, 1942, and rose to number 1 on October 31, where it stayed for 11 weeks. A holiday perennial, the song was repeatedly re-released by Decca, charting another sixteen times. It topped the charts again in 1945 and a third time in January 1947. The song remains the bestselling single of all time.[41] His recording of "White Christmas", has sold over 50 million copies around the world. His recording was so popular that he was obliged to re-record it in 1947 using the same musicians and backup singers; the original 1942 master had become damaged due to its frequent use in pressing additional singles. In 1977, after Crosby died, the song was re-released and reached No. 5 in the UK Singles Chart.[46] Crosby was dismissive of his role in the song's success, saying "a jackdaw with a cleft palate could have sung it successfully".[47]

Bob Hope, Marquita Rivera, and Bing Crosby in 1947

In the wake of a solid decade of headlining mainly smash hit musical comedy films in the 1930s, Crosby starred with Bob Hope and Dorothy Lamour in six of the seven Road to musical comedies between 1940 and 1962 (Lamour was replaced with Joan Collins in The Road to Hong Kong and limited to a lengthy cameo), cementing Crosby and Hope as an on-and-off duo, despite never declaring themselves a "team" in the sense that Laurel and Hardy or Martin and Lewis (Dean Martin and Jerry Lewis) were teams. The series consists of Road to Singapore (1940), Road to Zanzibar (1941), Road to Morocco (1942), Road to Utopia (1946), Road to Rio (1947), Road to Bali (1952), and The Road to Hong Kong (1962). When they appeared solo, Crosby and Hope frequently made note of the other in a comically insulting fashion. They performed together countless times on stage, radio, film, and television, and made numerous brief and not so brief appearances together in movies aside from the "Road" pictures, Variety Girl (1947) being an example of lengthy scenes and songs together along with billing.

In the 1949 Disney animated film The Adventures of Ichabod and Mr. Toad, Crosby provided the narration and song vocals for The Legend of Sleepy Hollow segment. In 1960, he starred in High Time, a collegiate comedy with Fabian Forte and Tuesday Weld that predicted the emerging gap between him and the new younger generation of musicians and actors who had begun their careers after World War II. The following year, Crosby and Hope reunited for one more Road movie, The Road to Hong Kong, which teamed them up with the much younger Joan Collins and Peter Sellers. Collins was used in place of their longtime partner Dorothy Lamour, whom Crosby felt was getting too old for the role, though Hope refused to do the film without her, and she instead made a lengthy and elaborate cameo appearance.[41] Shortly before his death in 1977, he had planned another Road film in which he, Hope, and Lamour search for the Fountain of Youth.

He won an Academy Award for Best Actor for Going My Way in 1944 and was nominated for the 1945 sequel, The Bells of St. Mary's. He received critical acclaim for his performance as an alcoholic entertainer in The Country Girl and received his third Academy Award nomination.[48]

Crosby and his family in a Christmas special, 1974

The Fireside Theater (1950) was his first television production. The series of 26-minute shows was filmed at Hal Roach Studios rather than performed live on the air. The "telefilms" were syndicated to individual television stations. He was a frequent guest on the musical variety shows of the 1950s and 1960s, appearing on various variety shows as well as numerous late-night talk shows and his own highly rated specials. Bob Hope memorably devoted one of his monthly NBC specials to his long intermittent partnership with Crosby titled "On the Road With Bing". Crosby was associated with ABC's The Hollywood Palace as the show's first and most frequent guest host and appeared annually on its Christmas edition with his wife Kathryn and his younger children, and continued after The Hollywood Palace was eventually canceled. In the early 1970s, he made two late appearances on the Flip Wilson Show, singing duets with the comedian. His last TV appearance was a Christmas special, Merrie Olde Christmas, taped in London in September 1977 and aired weeks after his death.[49] It was on this special that he recorded a duet of "The Little Drummer Boy" and "Peace on Earth" with rock musician David Bowie. Their duet was released in 1982 as a single 45 rpm record and reached No. 3 in the UK singles charts.[46] It has since become a staple of holiday radio and the final popular hit of Crosby's career. At the end of the 20th century, TV Guide listed the Crosby-Bowie duet one of the 25 most memorable musical moments of 20th-century television.

Bing Crosby Productions, affiliated with Desilu Studios and later CBS Television Studios, produced a number of television series, including Crosby's own unsuccessful ABC sitcom The Bing Crosby Show in the 1964–1965 season (with co-stars Beverly Garland and Frank McHugh). The company produced two ABC medical dramas, Ben Casey (1961–1966) and Breaking Point (1963–1964), the popular Hogan's Heroes (1965–1971) military comedy on CBS, as well as the lesser-known show Slattery's People (1964–1965).

Crosby in 1943

During the Golden Age of Radio, performers had to create their shows live, sometimes even redoing the program a second time for the West Coast time zone. Crosby had to do two live radio shows on the same day, three hours apart, for the East and West Coasts.[73] Crosby's radio career took a significant turn in 1945, when he clashed with NBC over his insistence that he be allowed to pre-record his radio shows. (The live production of radio shows was also reinforced by the musicians' union and ASCAP, which wanted to ensure continued work for their members.) In On the Air: The Encyclopedia of Old-Time Radio, John Dunning wrote about German engineers having developed a tape recorder with a near-professional broadcast quality standard:

[Crosby saw] an enormous advantage in prerecording his radio shows. The scheduling could now be done at the star's convenience. He could do four shows a week, if he chose, and then take a month off. But the networks and sponsors were adamantly opposed. The public wouldn't stand for 'canned' radio, the networks argued. There was something magical for listeners in the fact that what they were hearing was being performed and heard live everywhere, at that precise instant. Some of the best moments in comedy came when a line was blown and the star had to rely on wit to rescue a bad situation. Fred Allen, Jack Benny, Phil Harris, and also Crosby were masters at this, and the networks weren't about to give it up easily.

Crosby's insistence eventually factored into the further development of magnetic tape sound recording and the radio industry's widespread adoption of it.[74][75][76] He used his clout, both professionally and financially, for innovations in audio. But NBC and CBS refused to broadcast prerecorded radio programs. Crosby left the network and remained off the air for seven months, creating a legal battle with his sponsor Kraft that was settled out of court. He returned to broadcasting for the last 13 weeks of the 1945–1946 season.

The Mutual Network, on the other hand, pre-recorded some of its programs as early as 1938 for The Shadow with Orson Welles. ABC was formed from the sale of the NBC Blue Network in 1943 after a federal antitrust suit and was willing to join Mutual in breaking the tradition. ABC offered Crosby $30,000 per week to produce a recorded show every Wednesday that would be sponsored by Philco. He would get an additional $40,000 from 400 independent stations for the rights to broadcast the 30-minute show, which was sent to them every Monday on three 16-inch (41 cm) lacquer discs that played ten minutes per side at 33+1/3 rpm.

Murdo MacKenzie of Bing Crosby Enterprises had seen a demonstration of the German Magnetophon in June 1947—the same device that Jack Mullin had brought back from Radio Frankfurt with 50 reels of tape, at the end of the war. It was one of the magnetic tape recorders that BASF and AEG had built in Germany starting in 1935. The 6.5 mm ferric-oxide-coated tape could record 20 minutes per reel of high-quality sound. Alexander M. Poniatoff ordered Ampex, which he founded in 1944, to manufacture an improved version of the Magnetophone.

Crosby hired Mullin to start recording his Philco Radio Time show on his German-made machine in August 1947 using the same 50 reels of I.G. Farben magnetic tape that Mullin had found at a radio station at Bad Nauheim near Frankfurt while working for the U.S. Army Signal Corps. The advantage was editing. As Crosby wrote in his autobiography:

By using tape, I could do a thirty-five- or forty-minute show, then edit it down to the twenty-six or twenty-seven minutes the program ran. In that way, we could take out jokes, gags, or situations that didn't play well and finish with only the prime meat of the show; the solid stuff that played big. We could also take out the songs that didn't sound good. It gave us a chance to first try a recording of the songs in the afternoon without an audience, then another one in front of a studio audience. We'd dub the one that came off best into the final transcription. It gave us a chance to ad-lib as much as we wanted, knowing that excess ad-libbing could be sliced from the final product. If I made a mistake in singing a song or in the script, I could have some fun with it, then retain any of the fun that sounded amusing.

Mullin's 1976 memoir of these early days of experimental recording agrees with Crosby's account:

In the evening, Crosby did the whole show before an audience. If he muffed a song then, the audience loved it—thought it was very funny—but we would have to take out the show version and put in one of the rehearsal takes. Sometimes, if Crosby was having fun with a song and not really working at it, we had to make it up out of two or three parts. This ad-lib way of working is commonplace in the recording studios today, but it was all new to us.

Crosby invested $50,000 in Ampex with the intent to produce more machines.[77] In 1948, the second season of Philco shows was recorded with the Ampex Model 200A and Scotch 111 tape from 3M.[73] Mullin explained how one new broadcasting technique was invented on the Crosby show with these machines:

One time Bob Burns, the hillbilly comic, was on the show, and he threw in a few of his folksy farm stories, which of course were not in Bill Morrow's script. Today they wouldn't seem very off-color, but things were different on radio then. They got enormous laughs, which just went on and on. We couldn't use the jokes, but Bill asked us to save the laughs. A couple of weeks later he had a show that wasn't very funny, and he insisted that we put in the salvaged laughs. Thus the laugh-track was born.

Crosby started the tape recorder revolution in America. In his 1950 film Mr. Music, he is seen singing into an Ampex tape recorder that reproduced his voice better than anything else. Also quick to adopt tape recording was his friend Bob Hope. He gave one of the first Ampex Model 300 recorders to his friend, guitarist Les Paul, which led to Paul's invention of multitrack recording. His organization, the Crosby Research Foundation, held tape recording patents and developed equipment and recording techniques such as the laugh track that are still in use.[77]

With Frank Sinatra, Crosby was one of the principal backers for the United Western Recorders studio complex in Los Angeles.[78]

Mullin continued to work for Crosby to develop a videotape recorder (VTR). Television production was mostly live television in its early years, but Crosby wanted the same ability to record that he had achieved in radio. The Fireside Theater (1950) sponsored by Procter & Gamble, was his first television production. Mullin had not yet succeeded with videotape, so Crosby filmed the series of 26-minute shows at the Hal Roach Studios, and the "telefilms" were syndicated to individual television stations.

Crosby continued to finance the development of videotape. Bing Crosby Enterprises gave the world's first demonstration of videotape recording in Los Angeles on November 11, 1951. Developed by John T. Mullin and Wayne R. Johnson since 1950, the device aired what were described as "blurred and indistinct" images, using a modified Ampex 200 tape recorder and standard quarter-inch (6.3 mm) audio tape moving at 360 inches (9.1 m) per second.[79]

A Crosby-led group purchased station KCOP-TV, in Los Angeles, California, in 1954.[80] NAFI Corporation and Crosby purchased television station KPTV in Portland, Oregon, for $4 million on September 1, 1959.[81] In 1960, NAFI purchased KCOP from Crosby's group.[80] In the early 1950s, Crosby helped establish the CBS television affiliate in his hometown of Spokane, Washington. He partnered with Ed Craney, who owned the CBS radio affiliate KXLY (AM) and built a television studio west of Crosby's alma mater, Gonzaga University. After it began broadcasting, the station was sold within a year to Northern Pacific Radio and Television Corporation.

Crosby was a fan of thoroughbred horse racing and bought his first racehorse in 1935. In 1937, he became a founding partner of the Del Mar Thoroughbred Club and a member of its board of directors.[82][83] Operating from the Del Mar Racetrack at Del Mar, California, the group included millionaire businessman Charles S. Howard, who owned a successful racing stable that included Seabiscuit.[82] Charles' son, Lindsay C. Howard, became one of Crosby's closest friends; Crosby named his son Lindsay after him, and would purchase his 40-room Hillsborough, California estate from Lindsay in 1965.

Crosby and Lindsay Howard formed Binglin Stable to race and breed thoroughbred horses at a ranch in Moorpark in Ventura County, California.[82] They also established the Binglin Stock Farm in Argentina, where they raced horses at Hipódromo de Palermo in Palermo, Buenos Aires. A number of Argentine-bred horses were purchased and shipped to race in the United States. On August 12, 1938, the Del Mar Thoroughbred Club hosted a $25,000 winner-take-all match race won by Charles S. Howard's Seabiscuit over Binglin's horse Ligaroti.[83] In 1943, Binglin's horse Don Bingo won the Suburban Handicap at Belmont Park in Elmont, New York. The Binglin Stable partnership came to an end in 1953 as a result of a liquidation of assets by Crosby, who needed to raise enough funds to pay the hefty federal and state inheritance taxes on his deceased wife's estate.[84] The Bing Crosby Breeders' Cup Handicap at Del Mar Racetrack is named in his honor.

Crosby was married twice. His first wife was actress and nightclub singer Dixie Lee, to whom he was married from 1930 until her death from ovarian cancer in 1952. They had four sons: Gary, twins Dennis and Phillip, and Lindsay. Smash-Up: The Story of a Woman (1947) is said to be based on Lee's life. The Crosby family lived at 10500 Camarillo Street in North Hollywood for more than five years.[97] After his wife died, Crosby had relationships with model Pat Sheehan (who married his son Dennis in 1958) and actresses Inger Stevens and Grace Kelly before marrying actress Kathryn Grant, who converted to Catholicism, in 1957.[98] They had three children: Harry Lillis III (who played Bill in Friday the 13th), Mary Frances (best known for portraying Kristin Shepard on TV's Dallas), and Nathaniel (the 1981 U.S. Amateur champion in golf).[99]

Particularly during the late 1930s and through the 1940s Bing Crosby's domestic life was dominated by his wife's excessive drinking. His efforts to cure her with the help of specialists failed. Tired of Dixie's drinking, he even asked her for a divorce in January 1941. During the 1940s, Crosby consistently had difficulties trying to stay away from home while also trying to be there as much as possible for his children.[100]

Crosby had one confirmed extramarital affair between 1945 and the late 1940s, while married to his first wife Dixie. Actress Patricia Neal (who herself at the time was having an affair with the married Gary Cooper) wrote in her 1988 autobiography As I Am about a trip on a cruise ship to England with actress Joan Caulfield in 1948:

She [Joan Caulfield] was a lovely girl and we had some good talks. She, too, was in love with an older married man who was quite as famous as Gary [Cooper]. She confided to me that she desperately wanted to marry Bing Crosby. We were in the same boat in more ways than one, but I could not tell her so.[101]

In the most recent Crosby biography, Bing Crosby: Swinging on a Star; the War Years, 1940-1946, Gary Giddins published excerpts from an original diary of two sisters, Violet and Mary Barsa, who, as young women, used to stalk Crosby in New York City during December 1945 and January 1946 and who detailed their observations in the diary. The document reveals that during that time Crosby was indeed taking Joan Caulfield out to dinner, visited theaters and opera houses with her and that Caulfield and a person in her company entered the Waldorf Hotel where Crosby was staying. However, the document also clearly indicates that at their meetings a third person, in most instances Caulfield's mother, was present. In 1954, Joan Caulfield admitted to a relationship with a "top film star" who was a married man with children who at the end chose his wife and children over her. Joan's sister Betty Caulfield confirmed the romantic relationship between Joan and Bing Crosby. Despite being a Catholic, Crosby was seriously considering divorce in order to marry Caulfield. Either in December 1945 or January 1946 Crosby approached Cardinal Francis Spellman with his difficulties with dealing with his wife's alcoholism and his love for Caulfield and his plan to file for divorce. According to Betty Caulfield, Spellman told Crosby: "Bing, you are Father O'Malley and under no circumstances can Father O'Malley get a divorce." Around the same time, Crosby talked to his mother about his intentions and she protested. Ultimately, Crosby chose to end the relationship and to stay with his wife. Bing and Dixie reconciled and he continued trying to help her overcome her alcohol issues.[100]

Bing, Harry, and Nathan Crosby, 1975

Widow Kathryn Crosby dabbled in local theater productions intermittently and appeared in television tributes to her late husband.

In November 1958, Crosby purchased the 1,350-acre Rising River Ranch in Cassel, California after renting a portion of it for several years.[102] Attorney Ira Shadwell declined to disclose the purchase price. In October 1978, actor Clint Eastwood purchased the ranch under the name of his business manager Roy Kaufman for $1.5 million.[103]

Crosby and his family lived in the San Francisco area for many years. In 1963, he and his wife Kathryn moved with their three young children from Los Angeles to a $175,000 ten-bedroom Tudor estate in Hillsborough because they did not want to raise their children in Hollywood, according to son Nathaniel. This house went up for sale by its current owners in 2021 for $13.75 million.[104][105]

In 1965, the Crosbys moved to a larger, 40-room French chateau-style house on nearby Jackling Drive, where Kathryn Crosby continued to reside after Bing's death.[106] This house served as a setting for some of the family's Minute Maid orange juice television commercials.[104]

After Crosby's death, his eldest son, Gary, wrote a highly critical memoir, Going My Own Way (1983), depicting his father as cruel, cold, remote, and physically and psychologically abusive.[107] While acknowledging that corporal punishments took place, there were reports of all of Gary's immediate siblings distancing themselves from the abuse claims, either in public or in private.[100]

Crosby's younger son Phillip disputed his brother Gary's claims about their father. Around the time Gary published his claims, Phillip stated to the press that "Gary is a whining, bitching crybaby, walking around with a two-by-four on his shoulder and just daring people to nudge it off."[108] Nevertheless, Phillip did not deny that Crosby believed in corporal punishment.[108] In an interview with People magazine, Phillip stated that "we never got an extra whack or a cuff we didn't deserve".[108]

Shortly before Gary's book was actually published, Lindsay said, "I'm glad [Gary] did it. I hope it clears up a lot of the old lies and rumors."[100][108] Unlike Gary, Lindsay stated that he preferred to remember "all the good things I did with my dad and forget the times that were rough".[108] "Lindsay Crosby supported his brother (Gary) at the time of its publication but had a tempered view of its revelations. 'I never expected affection from my father so it didn't bother me,' he once told an interviewer.'"[109] However, after the book was published, Lindsay addressed the abuse claims and what the media had made out of them:

He was a good father. It was a happy childhood. We had our differences, but we were raised to respect our parents, to do what they said. If we didn't, we got punished. As far as I know [Gary] wrote it because it was about himself and what he felt his life was about. I don't think it had anything to do with Daddy Dearest. I understand what he's trying to prove. I don't think he did anything wrong.[110]

Dennis Crosby reportedly "said his older brother (Gary) was the most severely treated of the four boys. 'He got the first licking, and we got the second.'"[111]

Gary's first wife of 19 years, Barbara Cosentino, of whom Gary wrote in his book, "I could confide in her about Mom and Dad and my childhood",[112] and with whom Gary stayed friendly after the divorce, stated:

I do not know if what's in the book is true but he never said anything to me about whippings. I think it all got a little out of hand. I certainly never witnessed anything between him and his father. I couldn't believe it when I read the book because it just didn't sound like Gary. I can't pinpoint it. Gary said to me before I read it, "It's not the same book I wrote."[110]

Gary Crosby's adopted son, Steven Crosby, said in a 2003 interview:

In the early years, I think, like any family you are going to butt heads with your mom, your dad and your brothers and sisters. I think there was some father-son stuff that everyone has. The book was I think an attempt of my dad to come to grips with some things in his life.[113]

Bing's younger brother, singer and jazz bandleader Bob Crosby, recalled at the time of Gary's revelations that Bing was a "disciplinarian", as their mother and father had been. He added, "We were brought up that way."[108] In an interview for the same article, Gary clarified that Bing "was like a lot of fathers of that time. He was not out to be vicious, to beat children for his kicks."[108]

The author of the most recent biography on Bing Crosby, Gary Giddins, claims that Gary Crosby's memoir is not reliable on many instances and cannot be trusted on the abuse stories.[100][114]

Crosby's will established a blind trust in which none of the sons received an inheritance until they reached the age of 65, intended by Crosby to keep them out of trouble.[115] They instead received several thousand dollars per month from a trust left in 1952 by their mother, Dixie Lee. The trust, tied to high-performing oil stocks, folded in December 1989 following the 1980s oil glut.[116]

Lindsay Crosby died in 1989 at age 51, and Dennis Crosby died in 1991 at age 56, both by suicide from self-inflicted gunshot wounds. Gary Crosby died of lung cancer in 1995 at age 62, and Phillip Crosby died of a heart attack in 2004 at age 69.[117]

Bing Crosby and Kathryn Grant in 1960

Nathaniel Crosby, Crosby's younger son from his second marriage, is a former high-level golfer who won the U.S. Amateur in 1981 at age 19, becoming the youngest winner in the history of that event at the time. Harry Crosby is an investment banker who occasionally makes singing appearances.

Denise Crosby, Dennis Crosby's daughter, is also an actress and is known for her role as Tasha Yar on Star Trek: The Next Generation and for the recurring role of the Romulan Sela after her withdrawal from the series as a regular cast member. She also appeared in the 1989 film adaptation of Stephen King's novel Pet Sematary.

In 2006, Crosby's niece through his sister Mary Rose, Carolyn Schneider, published the laudatory book Me and Uncle Bing.

There have been disputes between Crosby's two families beginning in the late 1990s. When Dixie died in 1952, her will provided that her share of the community property be distributed in trust to her sons. After Crosby's death in 1977, he left the residue of his estate to a marital trust for the benefit of his widow, Kathryn, and HLC Properties, Ltd., was formed for the purpose of managing his interests, including his right of publicity. In 1996, Dixie's trust sued HLC and Kathryn for declaratory relief as to the trust's entitlement to interest, dividends, royalties, and other income derived from the community property of Crosby and Dixie. In 1999, the parties settled for approximately $1.5 million. Relying on a retroactive amendment to the California Civil Code, Dixie's trust brought suit again, in 2010, alleging that Crosby's right of publicity was community property, and that Dixie's trust was entitled to a share of the revenue it produced. The trial court granted Dixie's trust's claim. The California Court of Appeals reversed it, however, holding that the 1999 settlement barred the claim. In light of the court's ruling, it was unnecessary for the court to decide whether a right of publicity can be characterized as community property under California law.[118]

• Crosby, Bing. Call Me Lucky (1953)
• Crosby, Bing. Bing: The Authorized Biography (1975), written with Charles Thompson.