Famous for her trailblazing acting, modeling, and singing, Marilyn Monroe was undoubtedly one of the most coveted sex symbols of the 1950s and 1960. And, while she made a name for herself with her career, the late actress also made headlines with various love affairs in her life. While she was married only three times, Marilyn was involved in lots of affairs and flings, from married directors to A-list movie co-stars. Below, we have compiled some of Marilyn Monroe's most fascinating, and even controversial, romances.

James Dougherty, born on April 12, 1921, was a former Los Angeles police detective who won a place in Hollywood history when he married Norma Jean Baker in the early 1940s, years before she became the legendary sex symbol, Marilyn Monroe. He was her next-door neighbor, and they married in 1942.

However, once her husband, whom she dubbed Daddy, enlisted in the Navy, the marriage ended in divorce in September 1946. James remarried and had three kids after the divorce. In 1974, he retired and relocated to Maine, where he wrote and published two novels on his marriage to Marilyn.

Milton Berle was an actor who was born on July 12, 1908 and died on March 27, 2002. Berle's career as an entertainer stretched over 80 years, beginning with silent films and stage performances as a child actor, then moving on to radio, cinema, and television. He was the first big American television celebrity and was known to millions of viewers as ‘Uncle Miltie’ and ‘Mr. Television’ as the host of NBC's Texaco Star Theater.

According to Popsugar, Monroe and the comedian first met on the set of Ladies of the Chorus in 1948. Even though he was formally dating Adele Jergens at the time, Berle claimed to have had a short affair with the young actress.

Joe DiMaggio was an American baseball center fielder for the New York Yankees who was born on November 25, 1914 and died on March 8, 1999. He is widely regarded as one of the greatest baseball players of all time, possibly most remembered for his 56-game hitting streak. DiMaggio won the Most Valuable Player Award three times and was an All-Star in each of his 13 seasons.

Besides his incredible career, DiMaggio was also well-known for his marriage to and lifelong devotion to Marilyn Monroe. They married at San Francisco City Hall. The couple's marriage lasted barely nine months when Marilyn filed for divorce in 1954.

On August 6, 1917, Robert Mitchum, an American cinema actor, director, playwright, poet, composer, and vocalist, was born. Mitchum gained notoriety for his parts in numerous great noir films and is often regarded as a progenitor of the antiheroes popular in film throughout the 1950s and 1960s. In 1945, he was nominated for an Academy Award for Best Supporting Actor for his performance in The Story of G.I. Joe. The American Film Institute ranks Mitchum as the 23rd best male star of Classic American Cinema.

In 1954, he allegedly had a love affair with Marilyn Monroe. The pair met on the set of the 1954 film River of No Return, directed by Otto Preminger. However, the relationship was short-lived, with neither ever confirming it.

Elia Kazan was a filmmaker and author who was born on September 7, 1909 and died on September 28, 2003. He was famous for his theater achievements as well as his critically praised films. His reputation as one of the most brilliant and important American stage and film directors of the 1940s, 1950s, and early 1960s was tainted by his 1952 collaboration with the House Un-American Activities Committee, to which he ‘named names’, identifying fellow artists as Communist Party members.

While married to writer Molly Thacher, Kazan claimed to have a short romance with a young Monroe. In 1955, the filmmaker, who was then 55, confessed to his wife about his affair with a then-29-year-old Marilyn.

Marilyn married writer Arthur Miller for the third and last time in 1961. Arthur Miller was a playwright, writer, and controversial figure in twentieth-century American theater who was born on October 17, 1915. He wrote numerous scripts, the most well-known of which was The Misfits.

He was married to Marilyn Monroe during this period, received the Pulitzer Prize for Drama, and appeared before the House Un-American Activities Committee. Despite having first met in the early 1950s, they didn't start dating until after each had ended their relationship. They started dating in secret and got married in 1956.

Born on December 12, 1915, Frank Sinatra established a successful career as an award-winning singer and movie actor, making him one of the most well-known entertainers of the 20th century. He first became well-known for his big band vocals before receiving an Oscar for best supporting actor for his work in From Here to Eternity. Iconic songs like ‘Love and Marriage’, ‘My Way’, and ‘New York, New York’ are among the vast body of material he left behind.

Following Marilyn's divorce from Miller, The Blonde Bombshell dated Ol' Blue Eyes for a short while. By 1961, the relationship had cooled, although they remained close until her passing.

American actor and filmmaker Marlon Brando Jr. were born on April 3, 1924. He has a 60-year career and is highly known for his cultural impact on movies made in the 20th century. Terry Malloy in On the Waterfront and Don Vito Corleone in The Godfather are two of Brando's Oscar-winning roles. He is frequently credited as being one of the first performers to popularize Method Acting.

Marilyn Monroe and Marlon Brando co-starred in the movie Desiree and had a brief relationship a few years prior. According to Marlon in his 1994 autobiography, Songs My Mother Taught Me, the two stars struck up a friendship before Marilyn confessed her love for Marlon. It was also revealed that the actor was the last person Marilyn called before her death.

Actor Tony Curtis was born on June 3, 1925. In parts ranging from light humor to serious drama, he appeared in more than 100 films. In Sweet Smell of Success, he received his first significant acclaim for his dramatic acting. He was nominated for an Academy Award the following year for his performance in The Defiant Ones as Best Actor (1958). From 1949 through 1950, he claimed to have had a sporadic relationship with Marilyn Monroe. Even more, Tony Curtis acknowledged being the father of the child that the star was carrying when she was married to Arthur Miller.

Yves Montand was a well-known French theater and cinema actor and cabaret singer who was born on October 13, 1921. He had an appearance in the 1945 film Star Without Light, which was set in Paris. Before giving his most lauded performances in La Guerre est fine, his portrayal in Wages of Fear launched him to international recognition.

While Yves was married to Simone Signoret in 1951, he had an affair with Marilyn Monroe throughout the shooting. The actor decided to end their relationship and go back to his wife in France as his love for Marilyn grew.