The second son of megastar Bing Crosby and his first wife, jazz singer Dixie Lee, was born with twin brother Phillip in Los Angeles on July 13, 1934. The most reserved of the Crosby sons, Dennis was never interested in a show biz career although initially he halfheartedly pursued one. In the late fifties and early sixties he joined his brothers in a nightclub act billed as the Crosby Boys. In films, he appeared with his brothers in the 1945 movie Out of This World, played himself in Duffy's Tavern (1945), and had a bit part as "Private Page" in Sergeants Three (1962) starring Frank Sinatra and his fellow "Rat Pack" cronies Peter Lawford, Dean Martin, Joey Bishop, and Sammy Davis, Jr.
After leaving acting, Dennis worked in a production capacity for this father's company, Bing Crosby Productions. Like brothers Gary and Lindsay, he suffered from manic depression and alcoholism although he periodically achieved stints of sobriety through Alcoholics Anonymous. Unlike his brothers, however, Dennis downplayed the allegations of physical and emotional abuse made against their father by Gary Crosby in his 1983 tell-all book Going My Own Way. While admitting that older brother Gary was the prime target for their father's harsh discipline, Dennis added: "I was happy to be who I was even if I had the hell kicked out of me."
Professional and personal problems continued unchecked throughout Dennis' life. Shortly after his father's death in 1977, Dennis and his brothers learned that they would not immediately benefit from the crooner's demise. Instead, Crosby had set up a blind trust that was untouchable until his sons reached the age of 65. In December 1989, the brothers were informed by attorneys that the monthly four figure check each of them had received for years from a trust fund established by their late mother, Dixie Lee, was gone, wiped out by falling oil prices on the world market.
Eleven days after learning that there would be no more monthly checks, Dennis' favorite brother, Lindsay, fatally shot himself in the head on December 11, 1989. On May 4, 1991, two weeks after officially ending his 27 year second marriage, the 56 year old followed suit. Late that night, a roommate discovered Crosby's body lying on a couch in the living room of their modest home on Murphy Lane in the Black Point area of Novato, California. Depressed over finances, Lindsay's death, recurrent bouts of alcoholism, the divorce, and a recent breakup with a girlfriend, Crosby had shot himself in the head with a 12-gauge shotgun. The weapon was found lying at his feet beside the couch. Dennis Crosby was cremated and his ashes spread in the Novato area.