Top 10 Men in Old Hollywood Films Who Give Major Red Flags Now

The audience’s first introduction to this confident cowboy involves a stop at love interest Laurie’s farm. Curly wants her to know that he’s ready to take her to that evening’s box social. Of course, he never actually asked her to go with him. A heartbeat later, he’s making fun of the hired hand, Jud, who he sees as a rival. When Laurie goes with Jud instead of him, Curly flirts with other women to make her jealous. He also suggests to Jud that he should take his own life to see how many people like him enough to go to his funeral. This immature, rude, and frankly vile behavior makes it clear that Curly has a lot of growing up to do – to say the very least.

When this sharp-shooting star of Buffalo Bill's Wild West Show meets the scrappy Annie Oakley, he finds her ignorance charming. She’s infatuated and impressed by Frank and he likes that even more. However, their romance is quickly thrown off the rails when Annie proves to be not only a better shot, but a more popular act in the show. It would be great if Frank eventually overcame his insecurities and appreciated Annie for her skills and spunk. Instead, Annie pretends to lose a shooting contest to save his ego and “win her man”. We’re not sure we’d call that a true happily ever after… Or even a mediocre ever after!

Although Rhett Butler does seem to appreciate Scarlett’s personality quirks, he has some serious flaws as a romantic lead. Butler’s instinct is to mock and tease instead of revealing his true feelings. Throughout the film, he simultaneously belittles and compliments Scarlett. So, it’s not surprising that she struggles to believe he cares for her at all. However, what turns us off the most is how he forces himself on her. Later on, he forcefully kisses her again without consent in order to get her to stop talking. It only gets worse from there: after they’re married, she rejects him, so he picks her up and carries her to the bedroom despite a very ambivalent response from her. Nothing about that is OK.

The romantic lead in “Gigi” is introduced as a wealthy playboy who is bored of his glamorous life. He’s so disaffected that he realizes his current mistress must be seeing someone else, because she’s too happy to be thinking only of him. His charming reaction is to humiliate her in public. Later, when Gaston realizes he’s in love with his childhood friend, Gigi, his behavior towards her is more possessive than romantic. At best, this rich playboy is moody and cranky. At worst, he’s narcissistic and only interested in women when they do what he wants. Either way, we’re not impressed.

Gene Kelly’s starving artist, Jerry, doesn’t seem interested in improving his artistic abilities. He also objects to being sponsored by the beautiful and wealthy Milo. This contrarian behavior seems to be the foundation of his character. Even though he’s on a date with Milo, he flirts outrageously with Lise. When she says she’s not interested, he continually pesters her for her phone number. Despite her shut-downs, he later tracks her down at her job. Meanwhile, he continues to string Milo along. The single-minded pursuit despite rejection and disregard for the feelings of others is anything but endearing. It’s just a bad sign of things to come.

In this musical comedy, Adam, a 19th-century backwoodsman, leaves his isolated home and heads to town to snag a wife. He’s confident that any available, good-looking, hard-working woman will say yes to him. He’s even willing to pay her way through cooking school if necessary. What a nice guy! Adam eventually marries Milly, but doesn’t tell her about the house full of grown brothers she’s also expected to serve. Later, Adam convinces his brothers that they should kidnap the women they want to marry. He assures them that the ladies might act angry, but secretly they’ll be happy about it. We could not want to stay further away from this guy!

We’re willing to give Joe some slack for initially concealing his true identity from bandleader Sugar. After all, he and his friend Jerry pretend to be women and join the all-girl band to hide from the mob. Unfortunately, Joe passes up many opportunities to come clean. Instead, he uses the ruse to develop a pretend friendship with Sugar. Then, the shady musician creates a fake millionaire persona and tells a series of lies about his wealth and prestige. Even worse, Joe claims he’s suffered psychological trauma that makes him impotent and uninterested in women. If Sugar wants to marry into his money she has to prove that she can “cure” him of this problem. All we can say is, “Ew.”

When the recently poverty-stricken Blanche goes to stay with her sister, Stella, we aren’t supposed to swoon over brother-in-law Stanley. He’s portrayed as coarse, violent and demeaning. He physically mistreats his wife and sister-in-law and justifies it by saying he’s protecting his family. When he forces himself on Blanche and then has her put in a mental institution, it’s pretty clear he’s not meant to be a classic romantic lead. However, Marlon Brando’s portrayal has romanticized the character quite a bit in our culture. It doesn’t hurt that the actor was at the height of his macho good looks. Despite the dark charisma Brando gives him, Stanley Kowalski isn't a guy you want to add to your dating roster.

In the opening scene of this romantic comedy, the audience is given a glimpse of Dexter and Tracy’s marriage. As he leaves with his suitcases, she disdainfully breaks one of his golf clubs in two. Dexter's response is to rear back his arm as if to punch her, but then grab her face instead, and aggressively shove her through the door before he storms off. For the rest of the film, we’re supposed to root for him as he tries to win her away from a new wealthy fiancé. The chemistry between Katharine Hepburn and Carey Grant is undeniable, but their characters clearly have unresolved issues. Unfortunately, the violence in their earlier relationship makes it hard to think of their remarriage as a happy ending.

Before we unveil our top pick, here are a few honorable mentions.

Harold Hill, “Music Man” (1962)
The Wiser Girl Will Definitely Be Sadder if She Chooses This Con Artist

Paul Varjak, “Breakfast at Tiffany’s” (1961)
A Leading Man Who Gets Disturbingly Possessive When Rejected

James Bond, “From Russia With Love” (1963)
Bond Girls Are There to Serve This Spy However He Deems Necessary

Bill Calhoun, “Kiss Me Kate” (1953)
A Man Who Loves Gambling More Than His Girlfriend

Nathan Detroit, “Guys and Dolls” (1955)
A Gambler Who Continually Promises to Marry His Girlfriend & Then Bails

Although Professor Higgins is helping Eliza improve her status with elocution lessons, he doesn’t really see her as a human being. Instead, she’s the fascinating subject of his experiment. Like a true narcissist, every one of her victories is attributed to his own genius. Not to mention, he continually ridicules and insults Eliza, and women in general. Although the bachelor does miss her when she leaves, he doesn’t appear to learn anything from the experience. When Eliza returns, he treats her exactly as he did before she left. Sadly, it seems likely that he’ll notice his slippers more than the girl who’ll be fetching them.