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. This is our top 10 female list of celebrated stars who were also known as gangster molls.
Top 10 Female Stars and Their Mob Ties
10 Donna Reed
Despite winning an Oscar for her steamy turn as Alma (aka Lorene) in the 1953 classic From Here to Eternity, Donna Reed cultivated one of the most wholesome images of any actress in the mid‑20th century, especially when she embodied the ideal housewife Donna Stone in her eponymous television series. It’s therefore all the more surprising that she was romantically linked to mobster Johnny Roselli (sometimes spelled Rosselli) in the late 1940s.
Roselli, a dapper and charismatic figure, blended seamlessly into Hollywood society, also courting stars like Lana Turner and Betty Hutton. Though celebrated for his diplomatic finesse and dubbed “The Henry Kissinger of the Mob,” Roselli was also implicated in several murders, according to author Douglas Thompson.
9 Gloria Vanderbilt
Heiress‑turned‑actress and fashion designer Gloria Vanderbilt led a drama‑filled life from childhood through a famous custody battle, four vivid marriages, and a myriad of careers. One of her most turbulent chapters involved the abuse she later recounted at the hands of her first husband, Pat DiCicco, whom she married at 17. DiCicco, a film producer and agent, was allegedly tied to the Lucky Luciano crime family. Thirteen years her senior, he had previously wed actresses Thelma Todd and Linda Douglas.
Vanderbilt, visiting her mother when the engagement was announced, rushed into marriage to avoid returning to her aunt, the prominent society matron and artist Gertrude Vanderbilt Whitney, who had previously won custody of her. She quickly wed DiCicco after a breakup with millionaire Howard Hughes, who had employed DiCicco as a press agent. Whitney was so opposed that she removed her niece from her will. Vanderbilt soon realized the union was a mistake; DiCicco proved violent and emotionally abusive. She eventually divorced him in 1945, paying a $350,000 settlement.
9 Phyllis McGuire
The McGuire Sisters were among the most beloved female singing groups of the 1950s, famed for their wholesome, minister‑daughter image—until lead vocalist Phyllis McGuire sparked scandal with a romance with notorious Chicago mafia boss Sam Giancana.
Giancana first noticed McGuire when she performed with her sisters at The Desert Inn in 1959, subsequently erasing a sizable casino debt she owed. Though she testified before a grand jury in 1965 that they were merely friends, McGuire later admitted a romantic involvement, claiming she didn’t know who Giancana truly was when they met. Pressure from the FBI investigation, which even placed listening devices in her bedroom, and damaging publicity forced her to end the affair. She later dated oil‑man Edward “Tiger Mike” Davis, while Giancana was killed by an unknown assailant in 1975. Their passionate liaison inspired the 1995 HBO film Sugartime.
8 Dona Drake
Best known for roles in classics like Kansas City Confidential and The Girl from Jones Beach, the sultry Dona Drake was a familiar presence in the 1940s and ’50s. Beyond acting, she sang, danced, and led a band. Yet one of her most intriguing chapters involved a romance with Brooklyn racketeer Louis “Pretty” Amberg, who, alongside his brothers, sought to dominate local racketeering.
Amberg’s ambition ultimately led to his downfall; his body was discovered in a burning car in 1935. Police interrogated the then‑early‑twenties Drake, who claimed she knew him only as “Mr. Cohn” and was unaware of his criminal activities. Despite the scandal, Drake’s career flourished, and she later enjoyed a 45‑year marriage to Oscar‑winning costume designer Travilla.
7 June Lang
Johnny Roselli didn’t limit his charm to actresses; he married rising star June Lang in 1939. Though not as famous as some of his other girlfriends, the pretty blonde enjoyed a successful run in films such as Footlight Serenade and Stage Door Canteen, produced around the time of their marriage. Nevertheless, Lang’s tie to the mobster—dubbed “Handsome Johnny”—ultimately harmed her career.
When Roselli was off‑screen handling Chicago mob business in Hollywood and Las Vegas, he also dabbled in film production, co‑producing several pictures. Lang insisted she was unaware of his criminal dealings during their union. Given Roselli’s ability to present himself as anyone he wished, it’s plausible she truly didn’t know his true vocation. The revelation of his mob ties prompted Lang to file for divorce in 1943.
6 Lana Turner
The tempestuous love life of film icon Lana Turner featured several gangsters, but her most infamous liaison was with Cohen crime family affiliate Johnny Stompanato. Their relationship culminated dramatically when Turner’s 14‑year‑old daughter Cheryl Crane fatally stabbed Stompanato during a heated argument, fearing for her mother’s safety.
Stompanato’s possessiveness and violence were well documented; he not only assaulted Turner but also threatened co‑star Sean Connery, pointing a gun at him when he suspected an affair. On the night of his death, Turner was attempting to break up with Stompanato. Initially, she tried to protect her daughter by claiming responsibility herself, but the coroner’s inquest soon exonerated Cheryl, ruling the killing a justifiable homicide stemming from domestic violence. The case ignited one of Hollywood’s biggest scandals.
5 Jayne Mansfield
Considering the extensive time Colombo underboss Sonny Franzese spent in legendary nightclubs like the Copacabana, it’s unsurprising he crossed paths with high‑profile celebrities. Among those was iconic actress Jayne Mansfield, who, according to Crime Reads, was “madly in love with” Franzese.
The two met at The Latin Quarter nightclub, where Mansfield, a voluptuous blonde, appeared unexpectedly onstage and caught Franzese’s eye. At the time, she was married to bodybuilder‑actor Mickey Hargitay. When Mansfield warned Franzese that her husband would escort her home, Franzese allegedly threatened to beat Hargitay if he showed up. Their romance, however, remained casual as Franzese continued to “play the field.”
4 Jean Harlow
It’s easy to picture the brash, saucy Jean Harlow as a gangster’s moll, and she indeed dated infamous mobster Abner “Longie” Zwillman. In 1930, Zwillman bolstered Harlow’s fledgling career by loaning Columbia Pictures mogul Harry Cohn $500,000 in exchange for a two‑picture deal, propelling the 19‑year‑old from bit parts to stardom.
Harlow’s on‑screen roles often cast her as a gangster’s sweetheart, such as in Public Enemy (1931), cementing the flashy, brazen image of the 1930s moll. She married three times in her 26‑year life; after Zwillman—dubbed the “Al Capone of New Jersey”—her 1932 marriage to producer Paul Bern ended abruptly when Bern committed suicide just two months later.
3 Billie Holiday
Legendary jazz singer Billie Holiday endured a tumultuous personal life, plagued by addiction, an abusive childhood, and other hardships. Her love life added another layer of turbulence: her third and final husband, Louis McKay, whom she married in 1957, was a shady figure described as a wannabe gangster who abused her, stole her money, and allegedly worked as a mob enforcer.
The couple was once arrested together for narcotics possession. Holiday, fearing McKay, never reported his physical abuse. The final straw came when she learned he had lost her money in a risky venture. She left him, yet remained legally married until her death in 1959.
1 Marilyn Monroe
Given Marilyn Monroe’s wild, sometimes scandalous lifestyle, it isn’t surprising she tangled with high‑profile criminals. She’s been linked to several mobsters, including ladies’ man Sonny Franzese and reportedly Chicago boss Sam Giancana.
One of the most talked‑about rumors claims Giancana was with Monroe on her last full night alive, attempting to dissuade her from going public about an alleged affair with President John F. Kennedy. Monroe’s romance with Franzese formed a love triangle with ex‑husband baseball legend Joe DiMaggio, who remained infatuated with her. During Monroe’s famed “Happy Birthday, Mr. President” performance at a Madison Square Garden fundraiser, DiMaggio chased Franzese around the arena to confront him about the affair. Franzese later claimed he was ashamed for becoming involved with Monroe.