There have been few movie stars quite like Warren Beatty. The history of this Hollywood fixture stretches all the way back to the golden era, where he rubbed elbows with the most legendary stars out there. Having bridged the gap between decades of Hollywood history, Beatty has borne witness to Hollywood’s highest highs and lowest lows…and been at the center of quite a few of them himself. Forget the Moonlight incident—Beatty’s wildest moments are so much more jaw-dropping than just an envelope mix-up.
1. He Had Humble Beginnings
Considering the level of stardom that both Warren Beatty and his sister Shirley MacLaine have reached, you’d think that they’d have been born into a Hollywood dynasty. Well, their origins are as ordinary as they come. Beatty was born in Virginia, where his parents were teachers. Growing up, it was MacLaine who was the performer in the family—but Beatty wasn’t about to let his big sister leave him in the dust.
2. He Needed To Get Out
Beatty grew from an introspective bookworm into a strapping young high school football star—but it was clear that both siblings wanted to strike out on their own, far away from Virginia. Beatty could’ve easily left their hometown on a football scholarship, as colleges were chasing him down with generous offers. Still, he wanted to do things his way. And that’s exactly what he did.
3. He Made Up His Mind
Despite their many differences, Warren Beatty saw how quickly his sister Shirley moved through the ranks of Broadway and then Hollywood, and was incredibly intrigued. He hoped that an education at Northwestern might lead him there, but he only found disappointment. Beatty wanted to drop out, and his parents were horrified—but they knew that trying to stop him would only make him rebel more.
4. He Followed In Her Footsteps
Lightning doesn’t strike twice, and Beatty’s older sister had beaten him to the punch. Shirley MacLaine was already finding success, so the cards were stacked against him. Well, what’s a better motivator than sibling rivalry? After dropping out, Beatty moved to New York so that he could study under the legendary acting coach Stella Adler.
He also had to compete with scores of other hopefuls who hoped to follow in the footsteps of her famous former pupils—but not for long.
5. He Got A Late Start
Beatty may have seemed singularly focused on his career—but he had much more scandalous things on his mind. After all, you don’t become one of the most legendary playboys in Hollywood by mistake. However, despite his reputation, Beatty revealed that he was something of a late bloomer. Although he claims he was obsessed with sex by the age of 11, he only lost his virginity at the age of 20. Still, as we’ll see, he more than made up for lost time.
5. He Was An Instant Hit
Against the odds, Beatty turned a few bit parts on TV and in plays into a supporting role on Broadway. That was remarkable enough—and then Beatty got the surprise of a lifetime. His role garnered him a Tony nomination. With it came the invitation to Hollywood for a screen test. Beatty was just 22 years old, and quickly catching up to his big sister.
6. He Balked
There’s being in the right place at the right time, and then there’s being Warren Beatty. By the time he showed up to Los Angeles, producers were ready to fight each other to cast him—then he immediately made a grave mistake. He decided to sign with MGM Studios, and the script that they gave him was so bad that he panicked.
Beatty had to borrow money to pay them back so that they’d release him from his contract. He learned a hard lesson—and there were more on the horizon.
7. He Didn’t Want To Get Drafted
Beatty was determined to make his mark on the screen—and he wouldn’t let anything stand in his way. The Vietnam War was ramping up, and although it was years before the US would begin to draft young men to go fight there, Beatty saw the writing on the wall…so he came up with a plan.
8. He Played The Long Game
In February of 1960, Beatty joined the California Air National Guard. Strange plan for a kid who wanted to avoid service, right? Well, it was all part of the plan. A year later, Beatty got a dishonorable discharge. This made him ineligible for military service—and allowed him to pursue an acting career without worry of being drafted.
The timing couldn’t have been better.
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9. He Dated Up
Beatty wasn’t just occupied with his career. After spotting young starlet Joan Collins at a number of different Hollywood parties, Beatty took the plunge and called her for a date. She was four years older than him and well-established, but couldn’t deny the animal attraction. They began a passionate romance—but Collins quickly realized she was in over her head.
10. He Had Stamina
Joan Collins fell hard for Warren Beatty—but she faced an especially racy problem. Collins was no prude, but she simply couldn’t keep up with Beatty’s tireless libido. Completely worn out, she went to her friend Joanne Woodward for advice. Woodward’s reaction was less than sympathetic. She told Collins that if she wanted to stay with the “libidinous 22-year-old,” she’d better suck it up and keep up with him. Well, she gave it her best try…
11. He Was Up Against A Big Star
Finally, producers cast Beatty in his first film role, the lead in a picture called Splendor in the Grass. He was to perform opposite Natalie Wood, a former child actress who had been looking for the film that would make her a megastar. The two couldn’t have been more different. He was still “with” Joan Collins but had a wandering eye, while she was a young newlywed. It was his first film and she’d been in more than 30. He was a rising star, and many considered her washed up.
Despite their differences, both were struggling, and it seemed like Splendor would make or break them.
12. His First Film Was Torturous
Keyword: Break. The success of the film hinged on their performances as romantic leads, and director Elia Kazan knew it, pushing them to the brink in their scenes. As he forced them into embrace after embrace, their respective significant others watched from the sidelines. They were all playing a game of chicken, and Collins was the first to crack. She flew to Italy, leaving Wood’s husband Robert Wagner to babysit. He didn’t do the best job…
13. People Whispered About Them
Before long, the gossip columns were writing about how Beatty and Wood were practicing for their love scenes a little too intently, and a little too far from set. When Collins heard the news, she panicked. She rushed back from Europe for just two days—no small feat at the time—and confronted Beatty. Well, we all know what follows a fight, but their make-up went to the next level: Beatty proposed. This can't end well...
14. He Got Engaged
Collins went back to Europe with a ring on her finger, content that she’d shut down whatever was happening between Beatty and Wood. Whether that was true or not remains to be seen, but they successfully completed the film. They parted ways, each headed for their next big role—but history always repeats itself, especially when it comes to Warren Beatty.
15. It Happened Again
Beatty’s next role was opposite screen legend Vivien Leigh. She may have been more than two decades older than Wood, but the two had a lot in common. When Beatty met them, they were both struggling and vulnerable. Immediately, the pattern repeated itself, and the tabloids speculated that Beatty and Leigh were having an affair.
It served as good cover for the actual affair Beatty was having—with young actress Susan Strasberg. But he was still thinking of someone else, and it wasn’t Leigh or Collins…
16. He Went Back To Her
Natalie Wood had just hit a brick wall while filming West Side Story, sending her into another anxious tailspin over her career. The phone rang, and there was a familiar voice on the other end of the phone: Warren Beatty just couldn't forget about her. Before long, they were attending parties together, but this time, her husband Robert Wagner was less patient with their “friendship”—and frankly, I can’t blame him.
17. Their Significant Others Were Jealous
Wagner had a film wrapping up, and planned a party for it. Wood showed up late with Beatty, and then disappeared with him for a while. Later, they all went to a tense dinner with Collins. The next morning, Wagner and Wood’s press agents made a shocking announcement. They were separating. People obviously began to speculate why—but everyone in Hollywood already knew.
18. They Gave Up
Not-so-coincidentally, Collins kicked Beatty out of the apartment they shared around the same time. Beatty went to England to see her and they tried one more time to make it work to no avail. When another young actor caught Collins’ eye, she and Beatty finally called it quits—but as we’ll see, there was more to their split than met the eye.
19. He Chased Her
When Beatty came back to Los Angeles, he didn’t waste any time. He moved right into Natalie Wood’s rented Bel Air mansion. To give you an idea of how much Beatty was stoking the tabloid fires, this all happened before Splendor in the Grass even came out. And right around the time Beatty got together with Wood, it was time for them to promote the film.
It should’ve been their honeymoon period—it was more of a living nightmare.
20. He Hated What He Had To Do
Both actors went on a grueling press tour which was exacerbated by the laser focus on their relationship. It was like Beatty had signed a deal with the devil. He hated the scrutiny that came with being a star, and he hated talking about himself, his history, and his personal life. He made for a terrible interview—and quite honestly, he didn’t change much in the decades after.
Beatty is highly secretive, and a lot of what people know about him comes from other people, not by his own admission.
21. He Was A Massive Success
There was one saving grace, and that was the success of Splendor in the Grass. Beatty was disappointed that he didn’t get an Oscar nod when Wood had. Still, he got the award for “Most Promising Newcomer” at the Golden Globes. The next two films he’d made were slated to come out, coasting on Splendor’s success…but it turned out to be more of a slow skid.
Neither made the waves that Beatty wanted—and the results were disastrous.
22. He Didn’t Know What To Do
Beatty’s reaction to the bumps in the road of his career was to simply…freeze in place. He refused to take any script that was brought to him, even though they were clearly in his wheelhouse. His agents waited with bated breath after each delivery, only for him to rebuff them. A gossip columnist estimated he’d turned down 75 scripts and about $2 million in fees.
His personal life was already outshining his career, and he didn’t want to repeat the mistake. However, it totally backfired on him.
23. He Fanned The Flames
With nothing else to talk about, the columnists stopped writing about his acting talent and went back to speculating about his relationship with Natalie Wood. And he gave them more than enough to talk about. Wood and Beatty had been playing house for months, hosting parties for their Hollywood friends. Then, one night, when they were out in a group, Beatty simply…disappeared.
24. She Kicked Him To The Curb
Because Beatty doesn’t tell his own story—we can only collect it from the broken hearts he left in his wake—no one really knows where he went for the week he disappeared. Either way, when he showed up on Wood’s doorstep after a week of silence, it was the final straw. She dumped him and promptly took up with another man.
That year at the Oscars, she was up for Best Actress. Wood attended with her new beau—but she was in for a devastating surprise.
25. He Rebounded
Wood was up against Beatty’s sister Shirley MacLaine, and young actress Leslie Caron. As Caron entered the room, Wood looked up—and her blood ran cold. There on her rival’s arm was her ex, Warren Beatty. However, Wood wasn’t the only one they shocked that night. Beatty’s new paramour was married. Well, it hadn’t stopped them before…
26. His Comeback Was A Failure
With a new romance, Beatty also broke out of his professional rut, finally taking on a role in Lilith. Much like, ahem, dating a married woman, it was a big mistake. When it flopped, Beatty claimed he’d only taken it because he was broke—but everyone in Hollywood knew the truth. He’d cared about the film, and it was a crushing disappointment. And that wasn’t his only problem…
27. He Had To Pay For It
Caron’s soon-to-be ex-husband bristled at the sight of her and Beatty in the tabloid pages—so he lashed out. Beatty finally had to pay the price for his philandering. Caron’s ex named Beatty as a co-respondent in the divorce papers, and the judge actually ordered Beatty to pay the court costs for it all. Beatty’s solution? Make a film with Caron and let that pay the bills.
Yeah, his “choosiness” over films all of a sudden flew out the window…
28. He Was Self-Obsessed
Later, when the whirlwind of drama was done and Leslie Caron had time to reflect on the relationship, she had a disturbing revelation about Beatty. She remembered an instance where he had woken her up in the middle of the night and told her that he was worried she wasn’t thinking about him. At the time, she thought it was sweet, but she later realized that it was emblematic of his complete and total narcissism. Yikes.
29. She Gave Him A Gift
Beatty and Caron stayed together for two years, and he proposed multiple times, but his dramatic streak was too much for her, and they eventually broke up—but not before she introduced him to someone who would change his life. French director Francois Truffaut told Beatty he didn’t have a role for him in his newest project, but that he did have a script for him to read.
It was about a notorious pair of criminals—and Beatty was instantly intrigued.
30. He Had A New Fixation
Beatty had been adrift in his career, and Caron’s suggestion that he not only star in a film adaptation about the story of Bonnie Parker and Clyde Barrow, but also produce it, shook him out of his rut. Beatty always performed best when the cards were stacked against him, like when he first came to Hollywood. Once again, he was in an unwinnable situation—but he was determined to make it work.
31. He Had To Fight For It
Warren Beatty was ready to be at the forefront of the type of filmmaking that would eventually define New Hollywood—but unfortunately, the studios were still firmly entrenched in Old Hollywood thinking. Beatty brought the film straight to one of the most legendary figures in Old Hollywood, Jack Warner—and went to extreme lengths to convince him to make the film.
Not only did he agree to a tiny budget, he literally got down on the ground and was about to kiss Warner’s shoes before the old man told him to stop embarrassing himself.
32. He Found His Niche
And with that, at just 29, Beatty became not just an actor, but also a producer (and uncredited screenwriter). Having total control over a picture gave him the professional fulfillment he’d been searching for since he’d first come to Hollywood. It even gave him the, ahem, restraint he’d lacked in other ventures. Beatty and his female co-star, Faye Dunaway, vowed not to get involved with each other for the sake of the film—and surprisingly for Beatty, he actually kept his word.
33. He Almost Made Cher His Co-Star
Of course, that didn’t mean that he didn’t try to cast other actresses he’d already had flings with first. There was an attempt to bring on Natalie Wood (more on that later). Another surprising candidate? Cher. Yeah, that Cher. At the time, she was married to Sonny Bono, who thought appearing in such a “graphic” film would be terrible for her career. So, how did she know Beatty?
Well, they’d had a passionate affair a few years earlier, in 1962…when she was just 16 years old. Ew.
34. He Proved Himself
Against the odds—and the considerable efforts of Jack Warner, who hated the film and wanted it gone—Bonnie and Clyde became a beloved hit. It was a slow climb, and Beatty had to face criticism at first, but eventually, fans and critics grew to appreciate it. With that under his belt, Beatty let loose—and zeroed in on his next conquest.
35. He Met His Match
Warren Beatty had a type, and it was Oscar nominees. Well, now that he was a successful film producer, he decided to upgrade to a winner. When he met Julie Christie, sparks flew on both sides. They were a perfect match. Both were strong, stubborn, and outspoken. It actually wound up being one of his longer romances—but they hid a scandalous secret behind closed doors.
36. They Kept Things Casual
Beatty’s wandering eye had presented a problem in his previous romances, but it was less of an issue with Christie. They essentially had an open relationship, which alleviated that pressure. Regardless, Beatty did attempt to be a little more guarded when it came to romancing co-stars—though his status meant little on the set of his next film.
37. He Was Under A Watchful Eye
Beatty negotiated a generous paycheck to appear opposite Elizabeth Taylor in The Only Game in Town. Taylor’s husband Richard Burton was a fixture on set, perhaps because of Beatty’s reputation—and he kept a very close eye on them. Burton would stand behind the camera during their love scenes and make cutting remarks as soon as each take was over.
They got through it—but their timing couldn’t have been worse.
38. His Film Flopped
Taylor’s fame was fading fast, as was the popularity of the type of picture they’d just made. Audiences were far more interested in fare like Easy Rider and Midnight Cowboy—movies that probably wouldn’t have gotten funding had it not been for the success of Bonnie and Clyde. Beatty dusted himself off and recovered from the failure with Julie Christie and their friends in London.
Sadly, a horrific tragedy quickly shattered their serenity.
39. He Tried To Help A Friend
Two of Beatty and Christie’s closest friends in London were director Roman Polanski and his wife, actress Sharon Tate. Beatty rushed to Polanski’s side when the news of Tate's demise broke and helped his grief-stricken friend back to Los Angeles. There, he set up shop with other friends to make sure Polanski wouldn’t be alone. Beatty was a good friend, but even he had his limits—he later cut off Polanski during the latter’s infamous arrest and court case.
40. He Took His Time
Beatty entered another “quiet” period in his career, but this time, instead of frustration, it was a time of great creativity. He began to conceive of two movies that would come to define his career—Shampoo and Reds—but he would certainly take his sweet time making them. For Shampoo, he enlisted his girlfriend Julie Christie. They’d already appeared in one film together, and people loved their chemistry…but there was just one problem.
41. They Kept Holding On
Chemistry is a magical, ephemeral thing—and for Beatty and Christie, theirs was fading fast. She’d always been in monogamous relationships before, and was much more introverted and happy with a quiet life than Beatty was. Finally, they ended things, but it was a break-up with a looming reunion—after all, she had already committed to make Shampoo with him.
42. He Basically Played Himself
Warren Beatty is an intensely private person, but it would be hard to blame critics and fans for conflating his Shampoo character with his real life. In the film, he plays a philandering hairdresser juggling a handful of girlfriends, including characters played by Julie Christie and Goldie Hawn. Both of whom he’d happened to date. The similarities were too hard to miss—but he had an even more scandalous relationship in store.
43. He Dated His Friends’ Ex
Warren Beatty, Dennis Hopper, and Jack Nicholson were all part of a new generation of Hollywood A-listers in the 60s and 70s, and they all became close friends. But they had more than just that in common. They were all involved—not in that order—with musician Michelle Phillips. Beatty was the last to come along, and they even lived together in the first house he bought. Ever a confirmed bachelor, he had been living mostly in a hotel before that.
44. He Couldn’t Take The Scrutiny
History repeated itself with Beatty and Phillips. The press attention came, and Beatty balked, even dis-inviting her from the London premiere of Shampoo. Back at home, he promised her marriage and babies, and after it ended, it took her two years of therapy to realize that those promises had been empty. One thing was for sure: he did make a heck of a rebound.
45. He’s So Vain
Carly Simon’s hit song “You’re So Vain,” released in 1972, inspired a long conversation trying to identify who she was singing about. One of the more popular candidates for that dubious title was Beatty, with whom Simon had had a relationship. In 2015, after years of playing coy, Simon finally revealed the truth. She admitted that Beatty had inspired the song, but only the second verse.
Simon joked that Beatty thought the whole song was about him…which ultimately proves the lyrics in her song completely accurate!
46. He Couldn’t Resist His Co-Star
The next person to use Beatty as a rebound was Diane Keaton, fresh out of her relationship with her ex and frequent collaborator Woody Allen. Old habits die hard, and she worked with Beatty on his magnum opus, Reds, which came out in 1981. Reds won three Oscars, including Beatty’s only trophy, for Best Director—although the cast might not agree with that statement.
Beatty was such a taxing director that he demanded up to 80 takes for one scene. When an actress snapped at him about it, the entire crew applauded.
47. He Was Extra With The Extras
While he was filming Reds, Beatty was so dedicated to this story of the far-left-wing journalist John Reed that he would take the time to explain his story and his political causes so everyone working on the film knew what the film was truly about. While filming scenes in Spain, Beatty lectured the Spanish extras on the rights of the working man, which came back to bite him.
The extras left the sets en masse, refusing to return until they got fair wages for their work. For his part, Beatty agreed to the wage increase, recognizing a great moment of irony when it happened.
48. He Had A Last Hurrah
After Diane Keaton, Beatty went on to date model Stephanie Seymour, Janice Dickinson, Mary Tyler Moore, and Daryl Hannah. He even had a fiery—if short-lived—relationship with Madonna, his co-star in Dick Tracy. Little did he know, all these flings would serve as a sort-of “last hurrah” for his bachelordom…
49. He Knew Right Away
Warren Beatty met Annette Bening when she was auditioning to play Virginia Hill in the gangster biopic Bugsy. Reportedly, Beatty saw her audition and promptly telephoned director Barry Levinson and said something that surprised them both. He remarked “She’s terrific. I love her. I’m going to marry her.” Levinson, knowing Beatty’s reputation, didn’t think Beatty was serious, merely enthusiastic.
However, for once, Beatty happened to be true to his word.
50. He Almost Ruined It
Beatty’s reputation as a notorious ladies’ man nearly got in the way with Annette Bening when he wanted to settle down. According to Bening herself, many of her friends and family expressed concern with her relationship with Beatty. Some also commented on the fact that there's 21 years between them. However, she decided to take that risk—and it paid off.
51. He Transformed Himself
In 1992, after years of countless affairs and racy adventures, Beatty married actress Annette Bening. As if to further throw off his bad reputation, he went above beyond as a husband and father. The couple had four children together, and Beatty stayed out of the spotlight for many years to help raise them. They’re still going strong today—even through tumultuous times.
52. He’s A Supportive Dad
Beatty’s eldest child, Stephen Ira, was assigned female at birth, but later came out as transgender in 2006. Beatty has since referred to Stephen as a “revolutionary, a genius, and my hero, as are all my children.” Aww.
53. He Was Part Of A Mix-Up
In what must be one of the craziest moments in his life, let alone Oscars history, Beatty and his Bonnie and Clyde co-star Faye Dunaway introduced the Best Picture winner at the 2017 Academy Awards. However, the accountants overseeing the envelopes gave Beatty the wrong one. In his confusion, he handed it off to Dunaway, who mistakenly announced La La Land instead of Moonlight as the Best Picture winner—and that was just the beginning of the mess.
54. He Tried To Make It Right
In a shocking moment, producers rushed onstage to make the correction. Beatty tried to explain that the accountant had given him the wrong card. The media sensation took the world by storm. Beatty got a redo at the 2018 Academy Awards, when producers brought back him and Dunaway back to announce the Best Picture winner. Thankfully, things went smoothly the second time around.
55. He Was Really Living Up To His Character
Warren Beatty worked with a 17-year-old Carrie Fisher on the 1975 film Shampoo, and years later Fisher revealed the depths of his behavior during production. Not only had Beatty cast his ex-girlfriend and his then-current girlfriend in the film to play his character’s lovers, he also made a pass at Fisher, despite their age difference. She rejected him—making her one of very, very few women to say no to the notorious playboy.
56. He Reached Out To An Ex
When he was making Bonnie and Clyde, Beatty approached his ex-girlfriend Natalie Wood. He wanted to see if she would star as Bonnie. Her reaction was chilling. Wood cried and said she couldn’t bear the thought of appearing in any film, let alone one with him. Later that night, she tried to take her own life—and she didn’t act again for three years afterward.
It was also the last conversation they ever had before her untimely death.
57. It Was Too Close To Home
If there was bad blood between Natalie Wood and Warren Beatty, it’s no wonder—because in the 70s, he committed the ultimate betrayal. He actually ended up dating Natalie’s sister, Lana—but there was more to the story than meets the eye.
58. He Was Trying To Help Her
Lana had been in an abusive relationship. She had called Beatty to help her get out of it. She had no money and wasn’t speaking to Natalie. Beatty picked her up and got her a room at the Beverly Wilshire, where she stayed safely with her baby. Although they did end up involved, at least he had good intentions?
Of course, one of the most scandalous stories about Beatty goes all the way back to his first high-profile relationship…
59. They Nearly Had A Family Together
As mentioned earlier, Beatty’s relationship with Joan Collins was a serious whirlwind. Beneath the sheets, their love life was so passionate that she could barely keep up with him. However, that was the least of her problems. In her later memoir, Collins confessed a secret that she’d been keeping for years. Collins had once been pregnant with Beatty's child.
Fearing scandal and a ruined career, Collins opted for an abortion and never started a family with Beatty. When they called it quits, she walked away and never looked back.
60. He Had One Night With Marilyn
Another incident from early in Beatty’s career involves Marilyn Monroe—making Beatty was one of the last people to see her alive. A 25-year-old Beatty met her at a producer’s home during a party. According to a 2016 interview with Beatty, the two of them spent the evening together, which involved Beatty playing piano for her and a moonlit walk along the shore which he described as more soulful than romantic. Monroe died the next day.