Personal life

Crosby was married twice, first to actress/nightclub singer Dixie Lee from 1930 until her death from ovarian cancer in 1952. They had four sons (Gary, Dennis, Phillip, and Lindsay). Dixie was an alcoholic, and the 1947 film Smash-Up: The Story of a Woman is indirectly based on her life. After Dixie's death, Crosby had relationships with actresses Grace Kelly, Inger Stevens and Playboy model Pat Sheehan before marrying the much-younger actress Kathryn Grant in 1957. Bing and Kathryn had three children Harry, Mary (best known for portraying Kristin Shepard, the woman who shot J.R. Ewing on TV's Dallas), and Nathaniel.

Crosby reportedly overindulged in alcohol in his youth, and may have been dismissed from Paul Whiteman's orchestra because of it. He later got a handle on his drinking. A 2001 biography of Crosby by Village Voice jazz critic Gary Giddins says that Louis Armstrong's influence on Bing extended to his love of marijuana. Bing smoked it during his early career when it was legal and surprised interviewers in the 1960s and 70s by advocating its decriminalization, as did Armstrong. According to Giddins, Bing told his son Gary to stay away from alcohol (It killed your mother) and suggested he smoke pot instead. Gary said, There were other times when marijuana was mentioned and he'd get a smile on his face. Gary thought his father's pot smoking had influenced his easy-going style in his films. Crosby also smoked two packs of cigarettes a day until his second wife made him stop. He finally quit smoking his pipe and cigars following lung surgery in 1974.

Bing Crosby had an interest in sports. From 1946 until the mid-1960s, Crosby was part-owner of the Pittsburgh Pirates. In 1978, he and Bob Hope were voted the Bob Jones Award, the highest honor given by the United States Golf Association in recognition of distinguished sportsmanship in golf.

Crosby worked up until his death. Even in his final year, at the age of 73, after having broken his leg on a stage in Pasadena, California, he continued to perform. In his first performance after the accident -- his last American concert, on August 16, 1977 in Concord, CA -- the power went out, and he continued singing without amplification.

Shortly after 6:00 p.m. on October 14, 1977, Bing Crosby died instantly when he suffered a massive heart attack after a round of eighteen holes of golf in Madrid, Spain. He was 74 years old. His last words were reported as, That was a great game of golf, fellas. However, according to his companions and recorded by biographer Gary Giddins, Crosby then said, Let's go get a Coke. Because of incorrect instructions from his family, the year of birth engraved on Bing Crosby's tombstone is 1904, rather than the correct date of 1903. He was interred in the Holy Cross Cemetery in Culver City, California.

At his death, Bing was worth over $150 million because of his shrewd investments in oil, real estate, and other commodities, making him one of Hollywood's then wealthiest residents along with Fred MacMurray and best friend Bob Hope. A clause in his will stated that his sons from his first marriage could not collect their inheritance money until they were in their 80s. Bing felt that they had already been amply taken care of by a trust fund set up by their mother, Dixie Lee. All four sons continued to collect monies from that fund until their deaths. However, none lived long enough to collect any of their inheritance from their father.

After Bing's death, his image as an ideal father (fostered in part by his family's participation on his famous holiday television specials) was nearly destroyed when his eldest son, Gary, wrote a highly critical memoir (Going My Own Way) depicting Bing as cold, remote, and both physically and psychologically abusive. His son Phillip frequently disputed his brother Gary's claims about their father. In an interview conducted in 1999 by the Globe, Phillip is quoted as saying, My dad was not the monster my lying brother said he was, he was strict, but my father never beat us black and blue and my brother Gary was a vicious, no-good liar for saying so. I have nothing but fond memories of dad, going to studios with him, family vacations at our cabin in Idaho, boating and fishing with him. To my dying day, I'll hate Gary for dragging dad's name through the mud. He wrote Going My Own Way out of greed. He wanted to make money and knew that humiliating our father and blackening his name was the only way he could do it. He knew it would generate a lot of publicity. That was the only way he could get his ugly, no-talent face on television and in the newspapers. My dad was my hero. I loved him very much. He loved all of us too, including Gary. He was a great father.

Two of Bing's children, Lindsay and Dennis, committed suicide. It was widely published at the time of Lindsay's December 11, 1989 death that he ended his life the day after watching his father sing White Christmas on television. Dennis ended his life two years later, grieving over his brother's death, and battered, just as his brother had been, by alcoholism, failed relationships, and a lackluster career. Both brothers were subsisting on small allowances from their father's trust fund; both died of self-inflicted gunshot wounds to the head. Bing's son Phillip died in 2004; the media reported the causes as natural or unspecified. The coroner's decision not to publicly cite the specific cause of Phillip's death caused some to speculate that he also committed suicide.

Denise Crosby, Dennis' daughter, is also an actress and best known for her role as Tasha Yar on Star Trek: The Next Generation.

Nathaniel Crosby, Bing's youngest son from his second marriage, was a high-level golfer who won the U.S. Amateur at age 19 in 1981, becoming the youngest-ever winner of that event (a record later broken by Tiger Woods).