Inside '70s Heartthrob Warren Beatty's Bachelor Lifestyle Before Annette Bening

Now entering his 90s, Warren Beatty is long removed from his last feature-length film project — the 2016 period rom-com "Rules Don't Apply" — and even further removed from his heyday in the 1960s and '70s. Nevertheless, his name continues to be mentioned alongside those of the Tinseltown elite. And while his exploits as an actor and director have won fame and garnered accolades, it's not just his work in the film industry that cemented his legend.

Rather, it's his longstanding reputation as one of Hollywood's most notorious lotharios. While he's currently part of one of show biz's most enduring power couples — having been married to fellow actor and "Bugsy" co-star, Annette Bening, since 1992 — Beatty lived the ultimate bachelor's life beforehand. Between the late '50s and the early '90s, he romanced a veritable who's-who of entertainment's most desirable female stars. As a result, he reportedly finds himself standing shoulder to shoulder with celebs who claim to have slept with over 1,000 people. In Beatty's case, though, the hyperbole may just be true.

Here's a look at the bachelor years and wild lifestyle that Beatty left behind when he married Bening.

In the 2020s, Warren Beatty's status as one of the greatest movie stars of all time has been cemented for decades. However, there was a time when the "Dick Tracy" star wasn't even the top star in his own family. That's because he's the younger brother of Shirley MacLaine, who received her first Oscar nomination in 1959 — two years before Beatty made his big screen debut (she would later win an Oscar for her performance as Aurora Greenway in 1983's "Terms of Endearment").

If the two Hollywood icons had a sibling rivalry, though, it didn't impact their affection for one another. As noted by People in 2024, MacLaine actually considered herself Beatty's protector from an early age. "We're very close," she told the outlet. "We're very close. We don't let that be known, but we're very close." Despite that closeness, though, the siblings never worked on a movie together.

MacLaine was reportedly the pick for Bonnie in "Bonnie and Clyde" at one point, but the film's producers opted for a different approach once Beatty landed the other titular role. "I don't know what happened there," she said of their careers never merging in the way. "I was busy making my own [movies], and he was busy making his own. I guess there weren't parts that fit us together. I don't know. But we did not do it on purpose."

Given his charms and Hollywood career, it's no wonder Warren Beatty stole the hearts of many talented and beautiful women. However, the first famous female to become romantically linked to Beatty — another screen legend and eventual '80s icon, Joan Collins — actually began her relationship with the actor well before his big breakout.

The pair started dating in 1959 when, as Collins puts it, she was rebounding from an affair with director George Englund. "It's no secret anymore. I went with Warren [Beatty] sort of to get over George," she said in a 2023 interview with The Guardian. Nevertheless, their whirlwind romance ultimately led to their engagement. A year after their romance began, Collins was pregnant with Beatty's child. She was 26, and he was 23. However, as she writes in her memoir "Behind the Shoulder Pads: Tales I Tell My Friends," Beatty reportedly convinced her to terminate the pregnancy.

As noted by The Guardian, Beatty labeled the situation "terrible" and felt that Collins having the child would be detrimental to their respective careers. Looking back, though, Collins reportedly believes that ending the pregnancy was the right move, as she wouldn't have gone on to have her three children had she and Beatty proceeded. Beatty went on to link up with his "Splendor in the Grass" co-star Natalie Wood.

While Warren Beatty landed a handful of roles in the late 1950s — appearing in several episodes of CBS' "The Many Loves of Dobie Gillis" and guesting on series including NBC's "Suspicion" and CBS' "Playhouse 90," to name a few — he didn't make his big screen debut until 1961 with Elia Kazan's teen drama film "Splendor in the Grass." That's all it took to make him a Hollywood heartthrob, as his performance raised the eyebrows of critics and netted him a Golden Globe win as the "new star of the year."

"Splendor in the Grass" didn't just establish Beatty as a big-time star, though; it also saw him connect with one of his famous loves in his co-star, Natalie Wood. Wood had been married to actor Robert Wagner, but soon after the couple divorced, she was attending the Cannes Film Festival locked arm in arm with Beatty. "Together in public, they were something to behold," wrote Wood's sister, Lana Wood, of the couple in her 1984 book, "Natalie" (via The Hollywood Reporter). "Beautiful, exciting, sophisticated."

Their torrid affair — which may have begun when Beatty was still with Joan Collins — was short-lived, though. And, 10 years later, Wood remarried Wagner (who was there at the time of her mysterious death). Beatty, meanwhile, continued to build his legend on and off the screen.

Warren Beatty's list of rumored and confirmed lovers isn't just extensive — it's populated by some of the biggest names in entertainment history. One of those names was an icon of music and movies in Cher. However, Beatty and the "Believe" singer didn't link up on-set or at some swanky afterparty. Rather, they met by chance before Cher was famous, when Beatty reportedly cut her off while driving on Los Angeles' Sunset Boulevard.

"Pulling into the parking lot of the famous Schwab's Pharmacy, I jumped out and yelled, 'What the f**k's the matter with you? You almost hit me!'" Cher wrote in her 2024 book, "Cher: The Memoir, Part One" (via the Daily Mail/New York Post). "The man was wearing big, black-framed sunglasses, but I could still tell that he was unbelievably handsome, with one of the sexiest smiles I'd ever seen. When he took off his glasses, I realized that it was Warren Beatty."

Beatty promptly asked Cher out on a dinner date she accepted after remembering her mother was a fan of the actor. The two reportedly wound up at Beatty's place, where Cher found herself swimming in Natalie Wood's bathing suit. "Afterward, I drove home in a happy daze at 4am and found Mom and [step-father] Gilbert [LaPiere] standing on the doorstep in their nightclothes, furious that I'd defied my curfew again," Cher added, noting that they went on just two more dates.

While the mythos surrounding Warren Beatty's romantic liaisons is largely concerned with the women he successfully wooed, not every icon or ingénue he encountered was overcome by his charms. For her part, "Teacher's Pet" star Mamie Van Doren managed to keep Beatty at arm's length. While many details of Beatty's love affairs are fuzzy, Van Doren claims that she avoided the star despite his best efforts.

In her memoir, "Playing the Field," Van Doren — who was also involved in a legendary Hollywood feud — labeled Beatty "one of the most unusual of my many pursuers." According to Van Doren's recollection, Beatty first came calling at a party with Joan Collins. When Van Doren asked him about Collins, Beatty reportedly said something to the effect of, "....But that's no reason that you and I can't ... get together. Is it?" Van Doren responded by telling Beatty she wouldn't just "hop into bed" with him without getting to know him first. 

After their back and forth, Beatty failed to connect with Van Doren that night, according to the bombshell. He made subsequent attempts to woo her, reportedly bragging about his bedroom prowess, but, as Van Doren put it, their romance "never developed." Years later, she made headlines by telling People (via the Deseret News) that Beatty "drools a lot" when he kisses, adding, "He has such active glands."

While Warren Beatty found success more or less right off the bat with "Splendor in the Grass," he would cement his status as one of Tinseltown's ultimate leading men six years later when he starred in the 1967 Arthur Penn-directed crime drama "Bonnie and Clyde." Alongside Faye Dunaway (who played Bonnie Parker), Beatty's performance as outlaw Clyde Barrow brought him his first Oscar nomination as best leading actor. Dunaway was also nominated for best actress, while the film was nominated for best picture.

Beatty and Dunaway may have exhibited memorable chemistry on screen; however, an off-screen romance was apparently not in the cards for the legendary actors. However, they did become decades-long friends after working together. "My first impression of her was her no nonsense intelligence and her sense of humor," Beatty told People in 2017. "Of course I was struck by her beauty also and I knew she would be in for the long haul."

"Bonnie and Clyde" was followed by what was arguably Beatty's best period as a box office attraction, during which he starred in 1971's "McCabe & Mrs. Miller," 1974's "The Parallax View," 1975's "Shampoo," 1978's "Heaven Can Wait," and 1981's "Reds." Beatty racked up acting and directing nominations for the latter two films, winning a best director Oscar for "Reds."

During his early career, Warren Beatty famously engaged in a number of short-lived, highly-publicized affairs. However, as the '60s became the '70s and he settled in as a bona fide A-lister, Beatty found love of the long-term variety with another of his co-stars — British actor Julie Christie. According to The Daily Telegraph, the two stars met at a 1966 Royal Command performance of the wildlife drama film "Born Free," during which Beatty is said to have "fallen for Christie while watching her shake hands with the Queen."

They reportedly began dating others shortly thereafter; their relationship was kept under wraps at first, but the couple began appearing in public together around 1968, per The Telegraph. However, Beatty reportedly continued seeing other women while they were together, forcing her to break things off around 1973. Nonetheless, Christie has gone down as one of Beatty's most frequent collaborators, co-starring with him in "McCabe & Mrs. Miller," "Shampoo," and "Heaven Can Wait." And they have apparently remained good friends.

"It was very respectful," Beatty told People in 2016 of his romantic relationship. Added Beatty of the former flames' more recent dynamic: "When she and her husband come to Los Angeles, they stay in our guest house ... We're very close and she's a remarkable person."

Warren Beatty's affair with Bond girl Britt Ekland hardly rates among his most noteworthy. The pair linked up in 1970 after meeting at a party thrown by Roman Polanski. From there, the "Shampoo" actor got her into the mood for love by taking her to an adult film for their first date, after which the pair promptly left for a hotel room. 

During a 2013 episode of "Piers Morgan's Life Stories," Ekland recalled that she "probably felt [Beatty] was pretty wonderful for two weeks." When pressed by Morgan for more details about their relationship and Beatty, Ekland said the relationship was "a basic shag." In any case, Beatty seemingly made an impression on the Swedish star in at least one facet of their brief coupling.

"Warren could handle women as smoothly as operating an elevator," Ekland wrote in her 1980 memoir "True Britt" (via Peter Biskind's Beatty biography, "Star"). "He knew exactly where to locate the top button. One flick and we were on our way."

Cher wasn't the only musician Warren Beatty was romantically involved with over the years. He was also linked to folk icon Joni Mitchell and The Mamas & the Papas singer and actor Michelle Phillips. He made a lasting impression on the latter. "I was madly in love with him," Michelle told Vanity Fair in 2007. The two met when Beatty was with Christie and later moved in together after connecting on the set of "Shampoo."

However, their budding partnership was hindered in part by Phillips' big screen ambitions. "He wanted me to be with him all the time. When I told him I was going to do 'Valentino' [which would mean six months of filming], he said, 'Well, that's probably the end of our relationship,'" Phillips explained to the outlet. In the end, despite her desire to marry Beatty, the A-lister never popped the question.

Looking back, Phillips confessed that Beatty was a handful, and wished Beatty's longtime wife, Annette Bening, well in her own efforts to wrangle him. "I love Annette, and I pray for her every day!" Phillips said. "She can manage the guy, and I never could. He drove me nuts!"

When Warren Beatty achieved fame and won hearts in his 1961 film debut, Diane Keaton was one of the many women taken by his charms. "The first time I saw Warren was in 'Splendor in the Grass.' I mean, come on! He was, I mean, to die for. A Dream," Keaton told Variety in 2016, adding, "I mean, 'Bonnie and Clyde?' Come on. And not only was he beautiful, gorgeous, and sexy, and captivating, and mysterious, and a great movie star, but he was also an unbelievable producer and director."

Keaton and Beatty dated for five years, moving into the 1980s. It was during this time that Beatty cast her to play Louise Bryant, the love interest of his John Reed, in his 1981 film "Reds." It was a part that helped Keaton garner an Oscar nomination for best actress. Away from the camera, though, they couldn't make their long-term relationship work in the end. Still, the two stars remained great friends for many years thereafter. 

"I love her," Beatty told People of Keaton in 2016. "She's a combination of integrity and humor and intelligence and fairness and, did I say beauty? A brilliant comedic sense."

After dominating '60s and most of the '70s, Beatty appeared in just two films during the '80s. However, he returned as a leading man fray in 1990 big-screen adaptation of "Dick Tracy." While the film featured an ensemble cast, his most notable co-star was undoubtedly Madonna, who was at the height of her popstar powers. Despite their age gap, she and Beatty became romantically involved amid the film's production.

Beatty later described Madonna to People in 2016, saying, "She's a huge personality, diligent and disciplined and a spectacular dancer and performer," and adding that she was "perfect" for her part as Breathless Mahoney in "Dick Tracy." Their real life relationship was reportedly as brief as Tracy's own tryst with Mahoney in the film. According to People, the two had contrasting outlooks on living publicly, with Beatty initially declining to be part of Madonna's "Truth or Dare" documentary.

In the end, Beatty relented and appreciated she included a scene in which he questioned her desire to broadcast her life in the film's final cut. "I thought that was a kind gesture on her part because that captured how I felt," he told the outlet. "I was kind of touched by that because I felt that I said the right thing."

The legend of Warren Beatty's otherworldly way with women — and the relationships that it wrought — has ballooned to epic proportions across his seven decades in the Hollywood spotlight. In his Beatty book, "Star," biographer Peter Biskind mused about just how many female conquests the actor could claim, writing of Beatty allegedly saying that he couldn't sleep at night without having sex. Using his own speculative arithmetic, Biskind arrived at a shocking number: 12,775.

While the seriousness of Biskind's estimate can be debated, Beatty downplayed the figure during a 2016 AARP interview. "Think about it; sleeping with 12,775 people," he told the outlet. "That would mean not just that there were multiple people a day, but that there was no repetition." Added Beatty of his romantic exploits: "Look, I never misled anyone ... and I'm a nice guy."

In any case, while one might be tempted to say that Beatty remained on his legendary tear because he feared marriage and commitment, the "Heaven Can Wait" star offered an alternative theory during a 2016 appearance on NBC's "Today" (via Page Six). "I always felt I wasn't trying to avoid marriage, I was trying to avoid divorce. I had no doubt when I met Annette that it was time to get married."