The allure of Hollywood’s Golden Age and the smoky backrooms of nightclubs often intertwined with the dark world of organized crime. While many connections were business deals, the most captivating stories are the love affairs between famous actresses, singers, and other celebrities and infamous gangsters.
The fame of these women only amplified the shock when their relationships with dangerous men came to light. Here are ten celebrated stars who had romantic ties to the mob.
Donna Reed
Donna Reed, known for her wholesome image as Donna Stone in her TV series and her Oscar-winning role in From Here to Eternity, surprised many when it was revealed she dated mobster Johnny Roselli in the late 1940s.
Roselli, charming and handsome, moved easily within Hollywood circles, also dating Lana Turner and Betty Hutton. Known as “The Henry Kissinger of the Mob” for his diplomatic skills, he was also involved in murders, according to author Douglas Thompson.
Gloria Vanderbilt
Heiress, actress, and fashion designer Gloria Vanderbilt’s life was filled with drama, including a custody battle and multiple marriages. Her first husband, Pat DiCicco, whom she married at 17, was allegedly linked to the Lucky Luciano crime family, in addition to being a film producer and agent. He was also 13 years her senior and had been married to actresses Thelma Todd and Linda Douglas.
Vanderbilt married DiCicco to escape her aunt, Gertrude Vanderbilt Whitney, who had custody of her. Whitney disapproved of the marriage and cut Vanderbilt out of her will. DiCicco was abusive, leading to their divorce in 1945, with Vanderbilt paying him a $350,000 settlement.
Dona Drake
Dona Drake, known for her roles in films like Kansas City Confidential, was a singer, dancer, and bandleader. She was also the girlfriend of gangster Louis “Pretty” Amberg, who sought to control racketeering in Brooklyn alongside his brothers.
Amberg’s ambition led to his murder in 1935. Drake, questioned by police, claimed ignorance of his criminal activities, stating she only knew him as Mr. Cohn. She continued her successful career and was married to Oscar-winning costume designer Travilla for 45 years.
June Lang
Johnny Roselli married rising star June Lang in 1939. Lang, known for her roles in musicals like Footlight Serenade, saw her career suffer due to her connection with “Handsome Johnny.”
Roselli, involved in film production for the Chicago mob, co-produced films. Lang claimed she was unaware of his mob ties, which, while improbable, might have been true given Roselli’s ability to conceal his activities. She divorced him in 1943 upon discovering his criminal life.
Lana Turner
Lana Turner’s tumultuous love life included a relationship with Johnny Stompanato, an affiliate of the Cohen crime family. The relationship ended tragically when Turner’s 14-year-old daughter, Cheryl Crane, fatally stabbed Stompanato during a heated argument where she feared for her mother’s life.
Stompanato was known to be violent and possessive. He had assaulted Turner and threatened Sean Connery out of jealousy. Crane was exonerated after a coroner’s inquest ruled the stabbing a justifiable homicide due to domestic violence, sparking a major Hollywood scandal.
Jayne Mansfield
Colombo underboss Sonny Franzese, known for frequenting nightclubs, was romantically involved with several famous actresses, including Jayne Mansfield. Crime Reads reported that Mansfield was “madly in love with” Franzese.
They met at The Latin Quarter nightclub. Mansfield, married to Mickey Hargitay, told Franzese that her husband would be taking her home. Franzese threatened Hargitay, but the relationship was not serious for Franzese, who was involved with multiple women.
Jean Harlow
Jean Harlow, known for her brash persona, dated mobster Abner “Longie” Zwillman. Zwillman supported her career in 1930 by loaning Columbia Picture’s Harry Cohn $500,000 in exchange for a two-picture deal, helping her rise to fame.
Harlow often played gangsters’ girlfriends in films like Public Enemy (1931), creating the stereotype of the flashy gangster moll. Following her relationship with Zwillman, her marriage to producer Paul Bern ended when he committed suicide shortly after their wedding.
Billie Holiday
Billie Holiday’s personal life was difficult, marked by addiction problems and an abusive childhood. Her third husband, Louis McKay, whom she married in 1957, was a shady character who abused her, stole her money, and was a wannabe gangster. Reportedly, he worked as a mob enforcer.
The couple was arrested for narcotics possession. She feared McKay too much to report his violence. She left him after he lost her money in a business deal but was still married to him when she died in 1959.
Phyllis McGuire
Phyllis McGuire of the McGuire Sisters had a scandalous romance with Chicago mafia boss Sam Giancana. Giancana was drawn to McGuire when he saw her performing in 1959, canceling her casino debt.
McGuire initially testified she and Giancana were just friends but later admitted to a romantic relationship, claiming she didn’t know who he was initially. The affair damaged the McGuire Sisters’ career and upset her parents. McGuire was also caught up in an FBI investigation, and the couple was together for years. Eventually, McGuire became involved with Edward “Tiger Mike” Davis, and Giancana was murdered in 1975. Their relationship was portrayed in the 1995 movie Sugartime.
Marilyn Monroe
Marilyn Monroe was linked to numerous high-profile criminals, including Sonny Franzese and Sam Giancana. Giancana was reportedly with Monroe on her last full night alive, trying to dissuade her from revealing her affair with President John F. Kennedy.
Her romance with Franzese created a love triangle with her ex-husband, Joe DiMaggio. During the evening Monroe sang “Happy Birthday” to President Kennedy, DiMaggio chased Franzese around Madison Square Garden, confronting him about the affair. Franzese, who admired DiMaggio, was ashamed of the affair.
