Throughout entertainment history, some famous women have become just as well known for their independent approach to relationships as they have for their careers. From classic Hollywood stars to modern music icons, these women have often refused to follow traditional expectations about romance, marriage and dating.
For generations, society judged women far more harshly than men for having multiple relationships or choosing not to settle down. Fortunately, those attitudes have changed considerably. Today, successful women can make their own decisions about relationships and live life according to their own priorities.
The women featured below come from very different eras and backgrounds. Some had high-profile marriages, others were linked to famous entertainers, while several became cultural icons partly because they refused to conform to expectations. Their stories offer a fascinating look at celebrity relationships throughout the years.
15. January Jones
Best known for playing Betty Draper on Mad Men, January Jones has maintained a famously private personal life. One of the biggest mysteries surrounding her early years of motherhood involved the identity of her son's father, something Jones chose not to publicly reveal.
Over the years, entertainment media have linked her romantically with several well-known men, although many of the rumors were never confirmed. Rather than allowing speculation to define her, Jones has generally kept her family life away from the spotlight.
14. Lindsay Lohan
Lindsay Lohan became a major child star before reaching even greater fame with films such as Mean Girls. Her highly publicized personal life later became a regular source of headlines, including stories about her relationships with other celebrities.
A particularly memorable episode involved a handwritten list of famous people she had reportedly dated. The list generated considerable media attention because it contained several recognizable names. Whatever the truth behind every entry, Lohan has certainly experienced the intense public scrutiny that comes with celebrity relationships.
13. Cher
Cher has enjoyed one of the most remarkable careers in music and entertainment, and her romantic history has also attracted plenty of attention. Her relationships have included several famous musicians and actors, including Sonny Bono, Gregg Allman and Gene Simmons.
She has also been linked with younger men, including actors Val Kilmer and Tom Cruise during their younger years. Cher's willingness to ignore conventional expectations about age and relationships became another part of her larger image as an independent celebrity who has always done things her own way.
12. Julia Roberts
Julia Roberts has spent much of her career playing romantic characters, but her own love life has been every bit as dramatic as one of her movies. Her early relationships included actor Kiefer Sutherland, whom she was once engaged to marry before their wedding was called off.
She later married singer Lyle Lovett and had relationships with Benjamin Bratt and other prominent figures before eventually finding lasting happiness with cinematographer Daniel Moder. Their relationship has remained far more private than the romances that dominated headlines during Roberts' younger years.
11. Tyra Banks
As one of the world's most successful models and television personalities, Tyra Banks naturally attracted plenty of attention from famous men. Her reported dating history includes athletes, entertainers and other major names from the worlds of sports and entertainment.
Banks was linked to basketball stars such as Chris Webber and Rick Fox, as well as hockey legend Mark Messier. She was also rumored to have been romantically involved with Will Smith around the period when she appeared on The Fresh Prince of Bel-Air. Her relationships became another interesting chapter in the story of her rise from runway model to businesswoman and television mogul.
10. Drew Barrymore
Drew Barrymore's life has been unusually eventful since she became a child star. Her romantic history has included several engagements and marriages, many of which ended after relatively short periods.
Among her best-known relationships were marriages to Jeremy Thomas and comedian Tom Green, as well as a long on-and-off relationship with actor Justin Long. She also dated musician Fabrizio Moretti before marrying art consultant Will Kopelman. Barrymore's personal journey has been filled with changes, but she has continued to reinvent herself professionally throughout the years.
9. Elizabeth Taylor
Few Hollywood stars had a romantic history as famous as Elizabeth Taylor. The legendary actress married eight times during her life, making her relationships a permanent part of Hollywood history.
Her most famous romance was undoubtedly with Richard Burton. The pair married twice and divorced twice, creating a relationship filled with passion, arguments, reconciliations and enormous media attention. Taylor's marriages and relationships reflected the larger-than-life personality that made her one of Hollywood's most enduring stars.
8. Jennifer Lopez
Jennifer Lopez has had one of the most closely followed dating histories in modern entertainment. From her relationship with Sean “Puff Daddy” Combs to her marriage to singer Marc Anthony, her romantic life has frequently appeared in the headlines.
Perhaps the most famous chapter was her relationship with Ben Affleck. Dubbed “Bennifer” by the media, their romance became a pop-culture phenomenon. Lopez's later relationships, including her romance with dancer Casper Smart, continued to attract significant public interest.
7. Mariah Carey
Mariah Carey's enormous music career has been accompanied by a fascinating romantic history. Her first marriage was to music executive Tommy Mottola, who was significantly older and also played an important role in her early career.
After their divorce, Carey was linked to several prominent figures, including baseball star Derek Jeter and singer Luis Miguel. She later married Nick Cannon, with whom she shares children, before entering another high-profile relationship with Australian billionaire James Packer. Her personal life has often been nearly as headline-making as her music.
6. Ava Gardner
Ava Gardner was one of classic Hollywood's most celebrated stars, and her romantic life was almost as legendary as her acting career. Her relationships included famous figures such as Mickey Rooney, Artie Shaw, Howard Hughes and Ernest Hemingway.
Her marriage to Frank Sinatra became particularly famous. The relationship was intensely passionate and frequently covered by the press. Although their marriage ended, Sinatra remained an important figure in Gardner's life. Her glamorous image and string of famous relationships helped cement her reputation as one of Hollywood's great screen icons.
5. Rihanna
Rihanna's relationships have been closely followed throughout her rise from young singer to global superstar and entrepreneur. She has been linked with several famous figures, including athlete Matt Kemp, rapper Drake and other entertainers.
What makes Rihanna stand out is her fiercely independent public persona. Her career has never depended on having a famous partner, and she has repeatedly demonstrated that she can remain successful while keeping control of her own life. Her confidence and independence have become central parts of her public image.
4. Taylor Swift
Taylor Swift's romantic history has been closely connected to her songwriting since the beginning of her career. Several high-profile relationships have inspired songs, stories and endless media discussion.
Rather than allowing those relationships to define her, Swift has transformed personal experiences into one of the most commercially successful songwriting careers in modern music. Her dating history includes several famous entertainers, but her ability to turn emotional experiences into music has arguably become the most recognizable part of the story.
3. Marilyn Monroe
Marilyn Monroe remains one of the most famous celebrities in entertainment history, and her romantic relationships have been discussed for decades. She was married three times, including marriages to baseball legend Joe DiMaggio and playwright Arthur Miller.
Monroe was also famously linked to powerful figures in American politics, although some of the more sensational claims surrounding her personal life remain disputed. Behind the glamorous public image was an ambitious woman who wanted to be taken seriously as both an actress and an intelligent individual.
2. Angelina Jolie
Angelina Jolie's personal life has attracted enormous media attention throughout her career. Her early marriages to actors Jonny Lee Miller and Billy Bob Thornton became part of her famously unconventional public image.
Her relationship with Brad Pitt became an even bigger cultural phenomenon. The pair met while working on Mr. & Mrs. Smith, and their romance became one of the most closely watched celebrity relationships in the world. They eventually married and built a large family together before separating years later.
Beyond her relationships, Jolie has built a significant career as an actress, filmmaker and humanitarian. Her ability to establish an identity beyond celebrity romance has become an important part of her legacy.
1. Mae West
Mae West stands out as one of the earliest Hollywood women to openly challenge conventional ideas about female sexuality and independence. She was an actress, writer and performer who built her career around provocative humor and fearless self-expression.
West repeatedly challenged censorship and conservative attitudes, even facing legal trouble over some of her work. Rather than backing away from controversy, she turned it into part of her brand and became one of the highest-paid entertainers of her era.
Her personal life was also unconventional for the period. She was known for relationships with men of different ages and refused to conform to the expectations placed on women at the time. One famous story claims that when her partner William Jones faced discrimination at the building where she lived, West purchased the property and removed the restriction.
Whether every detail of that story has been embellished over the years or not, it perfectly captures the rebellious spirit associated with Mae West. Long before modern celebrities openly discussed independence and personal freedom, she had already made a career out of refusing to play by society's rules.
From Mae West and Marilyn Monroe to Jennifer Lopez, Rihanna and Taylor Swift, these women have each experienced relationships under an enormous public spotlight. Their stories are very different, but they share one common thread: each has challenged traditional expectations in her own way while building a lasting career in entertainment.