Six Degrees of Frank Sinatra? Exploring Sinatra’s connections through eight decades

Have you ever heard of the game “Six Degrees of Kevin Bacon?” The theory is that Kevin Bacon is such a prolific actor that you can name any actor and connect them to Kevin Bacon in six steps by tracing his co-stars and their movies. By the time Frank Sinatra died at age 82, he had rubbed elbows with so many actors, musicians, politicians and famous criminals that ‘six degrees’ could be applied to almost any well-known character from his generation.

Sinatra and politics

As a young Italian-American growing up in New Jersey, Frank was exposed to many local characters that shaped the Hoboken community. He felt the strain of being Italian-American in a time when many Italians were accused of having mob connections and were distinctly unpopular in many circles. Despite these challenges, however, his mother carved a space for her family as the owner of a local bar and his father became a member of the firefighter brotherhood. These early roots in New Jersey became the foundation for Sinatra’s lifelong support of “the little guy”, and he wanted to help politicians that also believed in elevating the common man.

His politics were based not only on his upbringing but also on a great deal of reading—Frank had begun reading in-depth books about politics and American literature while touring with the Dorsey Band. When Franklin Roosevelt ran for re-election in 1944 against Republican candidate Thomas Dewey, Frank became actively involved. Working with the Democratic Party, he appeared at fundraisers, spoke at Carnegie Hall, and appeared on broadcasts in support of Roosevelt. Frank was invited to and attended an afternoon reception at the White House during this time, even though it earned FDR some negative press for wasting time with a “crooner.” He appeared with FDR’s running mate, Harry Truman, and attended two to three campaign events a day in the days immediately prior to the election. Reportedly, Frank also made drunken threats to a journalist who opposed FDR, demonstrating his passion for the election and also his notorious lapses of judgement.

In early 1960, presidential hopeful John F. Kennedy made an appearance at one of Sinatra’s performances of “The Summit” at the Sands. By then, Frank had already thrown his support in behind Kennedy’s candidacy, much as he had with Roosevelt. JFK had youthful good looks and a beautiful wife and baby. The world saw him as a very clean-cut, moral young man and a veteran of World War II.

Frank and Kennedy had plenty in common, if rumors are to be believed. Both men were known to be womanizers and frequented questionable parties among the fashionable set. They were both idealistic as well, and Frank helped JFK with his campaign. Frank’s most important contributions to JFK’s elections came in the form of Frank’s musical anthems to JFK and his rumored use of Mafia connections.

Later in his career, Frank supported Ronald Reagan’s gubernatorial campaign and Nixon’s presidential campaign. Some theorized that he never got over slights paid to him by the Kennedy administration after they won the presidency, and began to support the Republican party. Others believe his Mafia connections deemed Republican causes to be more in line with their interests.

Sinatra and the Rat Pack

The Pack came together while Frank and fellow members were filming a movie called Some Came Running in a small town in Indiana. Frank and Dean Martin co-starred in the movie, in which a young Shirley MacLaine also had an important role. The two men made headlines for their bad behavior in the small town, drinking, carousing, and making fun of locals. The Rat Pack came to include Peter Lawford, Joey Bishop, and Sammy Davis Jr. The crew even developed their own lingo and nicknames for each other.

The Rat Pack suffered from mercurial personalities and frequent in-fighting amongst friends. Jealousy was rampant and public arguments were common. However, Frank created tight-knit connections with these four other performers that had successful careers and personal dramas. Through the “Pack”, Sinatra was linked with other famous celebrities, including Lauren Bacall, Kim Novak, Patricia Kennedy (sister to JFK), and more.

Sinatra’s Lovers

Frank married his sweetheart from his teenage years, but their marriage was famously fraught with difficulty. Frank was a well-known womanizer and continued to have affairs with other women after his marriage and the birth of their children. Lana Turner, Marlene Dietrech, Marilyn Maxwell and Zsa Zsa Gabor.

Sinatra had a long-term affair with Ava Gardner, who he ultimately married. Ava was a successful actress at the time, and their relationship featured public strife and unhappiness. They eventually divorced after several years where Frank chased Ava and she declined to commit to their marriage.

Frank’s third wife was another actress, 19-year-old Mia Farrow. Mia clearly did not fit in with Frank’s older friends and his Las Vegas casino crew of gangsters and hard-drinking performers. However, after a period of separation, Frank proposed to Mia in the summer of 1966. The marriage did not last very long. Predictably, the breaking point was over Mia’s career, which Frank wanted her to end. When Mia insisted on taking a promising role in the movie Rosemary’s Baby instead of filming a movie with him in November of 1967, he served her with divorce papers.

Sinatra’s Co-Stars

When your career is as long as Frank Sinatra’s, you predictably rack up quite a list of co-stars. For our “six degrees” exercise, we can have a spirited round of “name dropping”, to highlight some of his most famous collaborations.

Outside of the Rat Pack, Sinatra performed with top talent of his generation. He famously blew performances in front of Glenn Miller, Cole Porter and Tommy Dorsey, but he received a second chance with Tommy Dorsey and joined his band. Shortly thereafter he worked with Gene Kelly in Anchors Aweigh, showing off his dancing skills in the popular musical.

Another popular musical, Guys and Dolls, made Frank even more famous with his successful co-stars Marlon Brando, Jean Simmons, Frank Sinatra, and Vivian Blaine. Around the same time, he shared the screen with Bing Crosby and Grace Kelly in the 1956 romantic musical High Society.

One of Frank’s signature roles came in From Here to Eternity as “Maggio”, and the role reportedly relaunched his career after a difficult time. Sinatra starred with Hollywood heavyweights Burt Lancaster, Montgomery Clift, Deborah Kerr and Donna Reed.

How to play “Six degrees of Frank Sinatra”

While “Six degrees of Kevin Bacon” is limited to the movies and movie co-stars related to Kevin Bacon, one could name almost any celebrity from the 1950s-1970s and link them to Frank Sinatra through movie roles, singing performances, relationships or political association. The next time you are looking for a parlor game to amuse your friends, try “Six degrees of Frank Sinatra”, sure to be the next huge party trend!