Clark Gable

Clark Gable used to charm a lot of women back in the 1960s. He could effortlessly sweep any woman off their feet, credits to his incredible appeal. However, despite his romantic charm, his life was said to be unromantic. He was called a womanizer for the slew of women he had been with. He was even said to be a “serial seducer.”

He allegedly used his attractiveness to lure older women, who held powerful and influential positions in Broadway and Hollywood. This way, he could make it to the top without any sweat. Gable has even named a toyboy for that. Some of the women he was with were Loretta Young, Carole Lombard, and Lana Turner. Sadly, it was when his wife, Lombard, met her untimely demise that he began to see women.

Elvis Presley

Elvis Presley wasn’t only known for his excellent singing talent and dancing moves; he’s also famous for being a lover boy. Although he was popularly married to the lovely Priscilla Presley, they ended up parting ways. He had been with a lot of women before and after their marriage. However, his friend gave him the benefit of the doubt and said he wasn’t a womanizer at all.

He was never fond of sleeping with a girl but wanted a serious degree of the relationship itself. He’s in search of a true love that would last that long. Aside from Priscilla, some of the girls he had been with were Ann-Margret, Connie Stevens, Cybill Shepherd, Natalie Wood, Linda Thompson, Peggy Lipton, and several others.

Marilyn Monroe

Marilyn Monroe’s love life had been shrouded in secrecy. However, there were a lot of rumors about her affairs. Famed photographer Sam Shaw, who was also rumored to be one of her lovers, revealed if Monroe slept with every guy who was said to have been with her, she wouldn’t have the time to make any movies at all. At 16 years old, she was reportedly married to Jim Dougherty. Rumors also had it that she had a relationship with Charlie Chaplin’s son, Charlie Chaplin Jr.

Milton Berle and Monroe also, allegedly, had a thing when they met on the set of Ladies of the Chorus. However, at the time, he was dating Adele Jergens. She had a brief affair with Elia Kazan as well, who got the credits for being one of Hollywood’s all-time great directors, and more.

Jack Nicholson

Jack Nicholson famously had a longstanding relationship with Anjelica Huston. But aside from the iconic Adam’s Family actress, he seemed to have a penchant for models. His fame and good looks seemed to be his insurance in these girls’ hearts. The Shining star had been with the British supermodel, Kate Moss. He also dated Lara Flynn Boyle, who was half his age. He was also spotted with Cynthia Basinet, who was said to be his friend and lover.

Sharon Stone, one of the known supermodels back then, was seen watching a game with Nicholson in 1996. If that’s not enough, some of the girls Nicholson had been with were Amanda De Cadenet, Angie Everhart, Amber Smith, Julie Delpy, Tracy Richman, Ryan Ryan, and Marie Helvin, among others.

Madonna

At the peak of her career, Madonna had been with many men who also had a big name for themselves. During the 1980s to the 1990s, the Queen of Pop could effortlessly make any men fall for her even to this very day. With her fame, everybody wanted to know what was going on with her love life back then and who among the most famous guys she had been with.

The 1990s supermodel Tony Ward used to be Madonna’s boyfriend and muse. He had received several credits from her music videos and even made an appearance in her controversial coffee table book. Other famous stars that she had been with, and some would even surprise you, were Basquiat, Sean Penn, Warren Beatty, Lenny Kravitz, Tupac, Dennis Rodman, Carlos Leon, David Blaine, Vanilla Ice, Red Hot Chili Peppers’ frontman Anthony Kiedis, and Guy Ritchie, among others.

Pamela Anderson

Pamela Anderson used to be the woman who had been in every man’s dream back in the 1990s. She was an internal sensation who had a lot of high-profile relationships. She was often in the headlines for her controversial romances. Anderson had been married five times and called the help of her lawyers for four times. Her first husband was Tommy Lee. After three years, she wedded Kid Rock, and then Rick Salomon, followed by Jon Peters.

Anderson and Peters had a cute love story. He was one of her first boyfriends, but they eventually broke up. After over 30 years, they rekindled their romance and tied the knot in 2020. He’s currently her husband. But before she settled down, some of her ex-boyfriends are Marcus Schenkenberg and Adil Rami.

David Bowie

David Bowie had been in several relationships – both to men and women. Of course, he was famously married to Iman for 24 years. But before they tied the knot in 1992, he dated Melissa Hurley for three years and Bianca Jagger. Susan Sarandon also revealed he had an affair with Bowie in the 1980s and, to some degree, he was also linked to Elizabeth Taylor in 1982.

For four years, he had a relationship with Ava Cherry and dated Romy Haag for a year. Sabel Starr also admitted that she had an intimate romance with Bowie in 1973. Bebe Buell added that she, too, almost got intimate with the iconic singer. In case you didn’t know, he also had a thing with a fellow iconic singer, Mick Jagger. If this surprised you, he also had a fling with his guitarist Mick Ronson.

Marlon Brando

Marlon Brando didn’t only have a complicated love life, but also seemed to lose track of his kids. He had been with many women that he didn’t know to whom he had a child. In the 1950s, Brando proved he was a charmer. His incredible appeal lighted up the big screen that any woman he wanted could easily fall for him.

One of the too many women he had been with was Marilyn Monroe. He also had a 12-year romance with Rita Moreno, although it was on and off. However, things didn’t end up that well between the two to some degree. He also dated Pier Angeli, Shelley Winters, Nancy Qwan, and Katy Jurado. Through the 1970s, he had a romance with half a dozen women, like Yachio Tsubaki, a Zen master’s daughter.

Lana Turner

Lana Turner described love as “heels-over-chin, pinwheels-on-fire.” She firmly believed men were exciting, and if any women didn’t think so, they were as numb as a statue. In the book of her daughter, Cheryl Crane, she revealed a long list of men her mother had dated. However, some of them were just friendly dates, or nothing happened aside from goodnight kisses.

Turner had a huge crush on Wayne Morris. Her first studio romance was Ronald Reagan, although nobody knew if they had a relationship. She was also linked to Don Barry, while Mickey Rooney revealed they had a love affair. In his autobiography, Barry revealed several claims about Turner that she called her attorney to legally fight his statements. Other men she had dated were Robert Stack and Greg Bautzer.

Ursula Andress

Ursula Andress gets the credit for being one of the most beautiful and sexiest Bond girls in the movie Dr. No and the film’s parody, Casino Royale. Hence, it is no surprise that she had dated several men when she was young. However, she has only been married to one man, John Derek.

Andress had been in relationships with Jeff Speakman, Fausto Fagone for five years, Mario Natokis, Benny Silverstein for a year, Gianni Alfaro, Stan Herman, Paulo Roberto Falcao, and Lorenzo Rispoli for eight years. She dated Harry Hamlin for four years, Ricci Martin, Franco Nero, Fabio Testi for four years, Ryan O’Neal for six years, David Warner, Jean-Paul Belmondo for seven years, Marcello Mastroianni, and more. That’s quite a list, right?