There have been many links between organized crime and the entertainment industry over the years, especially during the Golden Age of Hollywood and the heyday of the nightclub circuit. While a lot of these associations were business related, some of the most exciting stories center on romantic relationships between gangsters and female movie stars, recording artists, and other celebrities.
The more popular these high-profile women were, the more shocking it was to learn they were dating or married to such infamous men. Here are 10 of the most celebrated stars who were also known to be gangster molls.
Related: 10 Famous Gangster Hideouts
10 Donna Reed
Despite her Oscar-winning performance as the sleazy Alma, aka Lorene, in the 1953 film From Here to Eternity, Donna Reed had one of the most wholesome personas of any actress during the mid-20th century, especially when she played the ideal homemaker, Donna Stone, in her self-titled TV series. That’s why it’s so surprising to learn that she dated mobster Johnny Roselli (sometimes spelled Rosselli) in the late 1940s.
The handsome, charming Roselli seems to have fit in well with the Hollywood crowd, also dating such stars as Lana Turner and Betty Hutton, among other actresses. Although he was known for his impressive diplomatic skills, being dubbed “The Henry Kissinger of the Mob,” Roselli was also involved in murders, according to author Douglas Thompson.
9 Gloria Vanderbilt
Heiress-turned-actress and fashion designer Gloria Vanderbilt had a drama-packed life from when she was a child to being the center of a famous custody trial through her four colorful marriages and various occupations. However, the prominent socialite experienced much turbulence, including the abuse Vanderbilt said she endured at the hands of her first husband, Pat DiCicco, whom she married at the age of 17. In addition to being a film producer and agent, DiCicco was also allegedly involved with the Lucky Luciano crime family. Nearly 13 years older than Vanderbilt, he had previously been married to actresses Thelma Todd and Linda Douglas.
Vanderbilt, who was visiting her mother at the time of the engagement, rushed into marriage because she didn’t want to go home to her aunt, the prominent society matron and artist Gertrude Vanderbilt Whitney, who had won custody of her years earlier. So she quickly married DiCicco following her break-up with iconic millionaire business magnate Howard Hughes, who was employing DiCicco as a press agent at the time.
The extremely wealthy Whitney was so opposed to the marriage that she cut her niece out of her will. It was obvious to Vanderbilt from the start that the union was a mistake. However, this was worse than an incompatible match. The ill-tempered DiCicco turned out to be violent and emotionally abusive. After a few years, she landed in the arms of her second husband, 63-year-old conductor Leopold Stokowski—who had his own issues. She divorced Pat DiCicco in 1945, paying him a settlement of $350,000.
8 Dona Drake
With her performances in such classic films as Kansas City Confidential and The Girl from Jones Beach, the sultry Dona Drake was a familiar face in the 1940s and ’50s. In addition to acting, she was also a singer/dancer and bandleader. But one of her most interesting roles had nothing to do with show business. She was the girlfriend of gangster Louis “Pretty” Amberg, who, alongside his two brothers, tried to take charge of racketeering in Brooklyn.
Ambition turned out to be Amberg’s downfall. In 1935, his body was found in a burning car. Police questioned the starlet, who was in her early twenties at the time. Drake said she didn’t even know what line of work Amberg was in or what his real name was, claiming she only knew him as Mr. Cohn. Not only did Drake go on to have a successful career, but her personal life also flourished. She was married to Oscar-winning costume designer Travilla for 45 years.
7 June Lang
Johnny Roselli didn’t just date beautiful actresses; he married rising star June Lang in 1939. She may not have been as famous as some of his girlfriends, but the lovely blonde, blue-eyed June did have a successful career with such movies as Footlight Serenade and Stage Door Canteen, musicals that were made around the time of her marriage to Roselli. However, Lang’s connection to this mobster, dubbed “Handsome Johnny,” ultimately hurt her career.
When Roselli was not working in Hollywood and Las Vegas on behalf of the Chicago mob, he dabbled in film production, actually co-producing a few movies. June claimed she was unaware of his mob ties during their marriage. As improbable as this may sound on the surface, there’s a good chance that Lang really was in the dark about her husband’s primary line of work since his connection to organized crime was not widely known in Hollywood at the time. He also had a talent for being whatever anyone wanted him to be. It was supposedly the discovery of his criminal activity that prompted Lang to leave him. The couple divorced in 1943.
6 Lana Turner
The stormy love life of film icon Lana Turner included more than one gangster, but the blonde beauty’s most famous relationship was with Cohen crime family affiliate Johnny Stompanato, not so much for the tumultuous relationship itself but for the way things ended. Stompanato was killed in 1958 by Turner’s 14-year-old daughter Cheryl Crane, who stabbed the mobster to death when he and Turner were having a very heated argument, during which Crane feared for her mother’s life.
It seems that her anxiety was warranted, considering the extremely possessive Stompanato was known to be violent toward Turner. Not only had he assaulted her but Stompanato, who was insanely jealous, also threatened Turner’s co-star Sean Connery by pointing a gun at him when he suspected the two of having an affair.
On the night of the fatal stabbing, Turner was trying to break up with Stompanato. Initially, Turner tried to protect her daughter by telling authorities that she was the one who killed Stompanato. However, it soon became clear that Cheryl was responsible. The adolescent was exonerated following a coroner’s inquest that concluded the stabbing was a justifiable homicide due to domestic violence. Naturally, the case sparked a huge scandal, one of the biggest in Hollywood history.
5 Jayne Mansfield
Considering all the time Colombo underboss Sonny Franzese spent at legendary nightclubs like the Copacabana, it makes sense that he would have become acquainted with various celebrities. But it is a little surprising to learn that he was romantically involved with some of the most famous actresses of the 1950s and ’60s, including Marilyn Monroe and Diahann Carroll.
According to Crime Reads, iconic movie star Jayne Mansfield was “madly in love with” Franzese. The night they met at The Latin Quarter nightclub was a memorable one.
Franzese was stunned to see the voluptuous blonde looking down at him from the stage where she had unexpectedly appeared. Mansfield was married to famous bodybuilder and actor Mickey Hargitay at the time. When she told him that her husband would be taking her home that night, Franzese threatened to beat him up if he came to the club. However, the relationship was not a serious one for the handsome mobster who was busy playing the field.
4 Jean Harlow
It’s easier to envision the brash, saucy Jean Harlow as a gangster’s moll than most of these actresses. The legendary platinum blonde siren dated infamous mobster Abner “Longie” Zwillman. He backed the young actress’s career in 1930 by loaning Columbia Picture’s mogul Harry Cohn $500,000 in exchange for giving Harlow a two-picture deal. The 19-year-old divorcee had mostly appeared in bit parts until then. The early 1930s films she starred in for Columbia and MGM skyrocketed her to fame.
In what could be seen as a case of art imitating life, Harlow was cast as gangsters’ girlfriends in a number of movies such as Public Enemy (1931). She would help to create the flashy, brazen, hard-edged image moviegoers had of gangster molls in the 1930s, one that would become a long-lasting stereotype. Married three times during her 26 years, Harlow’s love life was filled with drama. Following her relationship with Zwillman, who was dubbed the Al Capone of New Jersey, her 1932 marriage to producer Paul Bern ended when he committed suicide just two months after the wedding.
3 Billie Holiday
It’s no secret that legendary jazz singer Billie Holiday had a very troubled personal life. Between her well-documented addiction problems and her abusive childhood, as well as other adversities, it is amazing she was able to accomplish so much during her 44 years. Lady Day’s love life was another source of turbulence. Her third and last husband, Louis McKay, who she married in 1957, was a shady character, who abused Holiday, stole her money, and was described as a wannabe gangster. He did reportedly work as a mob enforcer and may have been involved in other criminal activities.
The couple was arrested together, at one point, for possession of narcotics. She was too afraid of McKay to report the physical violence he inflicted on her to the police. The last straw came when she found out he had lost her money in a risky business deal. She left McKay but was still married to him when she died a short time later, in 1959.
9 Phyllis McGuire
The McGuire Sisters was one of the most popular female singing groups of the 1950s. The trio of minister’s daughters also had one of the most straight-laced images until glamorous lead singer Phyllis McGuire began a scandalous romance with notorious Chicago mafia boss Sam Giancana.
Giancana was drawn to McGuire when he saw her performing with her sisters at The Desert Inn in 1959. He subsequently arranged to cancel the large debt she owed the casino. Even though McGuire testified before a grand jury in 1965 that she and Giancana were just friends, she later admitted they’d had a romantic relationship. Still, she explained in a televised interview that she did not know who he was when they first met.
In love but feeling pressure to end the romance since the bad publicity was heavily damaging the McGuire Sisters’ career and upsetting their parents, she was conflicted. Besides taking a toll on her professional life, McGuire was also caught up in an FBI investigation targeting Giancana. The agents even planted listening devices in her bedroom.
The couple was together for a number of years. But McGuire eventually became involved with oil-man Edward “Tiger Mike” Davis, and Giancana was shot to death by an undetermined assailant in 1975. Giancana and McGuire’s passionate relationship was depicted in the 1995 HBO movie Sugartime.
1 Marilyn Monroe
In light of Marilyn Monroe’s wild, sometimes scandalous lifestyle, it almost seems par for the course that she would have dated a gangster at some point. However, Monroe, who was rarely one to do things on a small scale, has been romantically linked to numerous high-profile criminals, including ladies man Sonny Franzese and reportedly Chicago mob boss Sam Giancana.
Marilyn was a very different type from the woman Giancana was most famously involved with, the clean-cut singer Phyllis McGuire. Something that has received a lot of attention is, according to many sources, Giancana was with Monroe on her last full night alive, during which he tried to talk her out of going public about her alleged affair with President John F. Kennedy.
Her romance with Franzese was part of a love triangle with her ex-husband, baseball great Joe DiMaggio, who was still in love with her. The memorable evening that Monroe sang “Happy Birthday” to President Kennedy during a Democratic fundraiser at Madison Square Garden, DiMaggio was chasing Franzese around the arena in an attempt to confront him about the affair. Franzese was trying to avoid the meeting because he admired DiMaggio. As he later claimed, he was ashamed of himself for getting involved with Monroe.