When people think of classic rom-coms, titles like Breakfast at Tiffany’s or Pillow Talk usually pop up. But S*x and the Single Girl (1964)? It’s often glossed over—despite being one of the sassiest, most star-packed comedies of its era. So let’s peel back the curtain and explore the lesser-known facts that made this film a bold, unforgettable marker of its time.

Inspired by a Groundbreaking Book… But Not Really

Sure, the movie shares its name with Helen Gurley Brown’s explosive bestseller, S*x and the Single Girl, but that’s about where the similarities end. The book was a fearless guide encouraging single women to live life on their own terms—scandalous in 1962. But the film? It’s a cheeky, fictional love story dressed up in high heels and punchlines. Rather than diving into the gritty truths of independent womanhood, it turned into a farcical romantic romp filled with identity mix-ups and classic misunderstandings.

Natalie Wood Wasn’t the First Choice

It’s hard to picture anyone else delivering the mix of wit, charm, and elegance that Natalie Wood brought to the role of Dr. Helen Brown. But fun fact: she wasn’t the original pick. Producers initially eyed Shirley MacLaine for the part. Due to scheduling conflicts, the opportunity passed to Natalie—who turned it into one of her most memorable performances. Her crisp delivery and expressive eyes added depth to a role that could’ve easily been played for fluff.

Video: Sex and the Single Girl – finale

A-Listers Galore: Star Power in Every Frame

This movie didn’t just rely on a catchy title. It brought out Hollywood royalty. We’re talking Tony Curtis, Lauren Bacall, Henry Fonda, and of course, Natalie Wood. With a cast like that, you’re not just watching a film—you’re witnessing a cultural moment. It’s like the Avengers of 1960s rom-coms. Every scene drips with charisma and polished star wattage.

Tony Curtis Loved Playing the Charming Impostor

Curtis had a knack for playing characters pretending to be someone they’re not. Remember Some Like It Hot (1959), where he masqueraded as a millionaire to woo Marilyn Monroe? Well, S*x and the Single Girl finds him back in familiar territory—this time impersonating a friend’s husband to get close to Dr. Brown. It’s a familiar formula, but Curtis works his magic with a wink and a grin, making deception look dangerously romantic.

Helen Gurley Brown Visited the Set—and Loved It

Though the movie strayed far from her feminist messaging, the author herself didn’t seem to mind. Helen Gurley Brown dropped by the set during filming and found the entire production process delightful. Even if the storyline didn’t mirror her book’s empowering manifesto, she appreciated its visibility and the attention it brought to her name and ideas.

The Title Stirred Controversy—And That Helped

Back in the ’60s, even the word “single” attached to a woman was enough to raise eyebrows. Add the word “girl,” and you’ve got a PR firestorm. Some critics and audiences felt the film’s title was a little too spicy for its own good. But controversy creates conversation—and conversation sells tickets. The title became a magnet for attention, catapulting the movie into box-office success and late-night talk show debates.

A Car Chase… In a Romantic Comedy? Yep.

You’d expect emotional monologues or grand gestures in a romantic comedy—not a slapstick car chase. But that’s exactly what you get in the film’s climax. The wild, exaggerated pursuit down L.A. streets plays like a Looney Tunes segment, packed with sight gags and ridiculous stunts. It’s so over-the-top it feels like it crashed in from another movie—but somehow, it works. It adds a final comedic punch that makes the ending memorable.

Tony Curtis Crosses Gender Lines for Laughs

In a scene that might not fly the same way today, Curtis dons a disguise to pass as a married man—complete with awkward domestic interactions. This “crossing the line” identity swap was a common trope of the time, used to stir up giggles and confusion. And it worked. Curtis’s performance had audiences laughing while subtly playing with ideas of social roles and expectations.

Natalie Wood’s Iconic Wardrobe Came From a Legend

Video: Sex and the Single Girl (1964) – Henry Fonda – Lauren Bacall -Dance

One of the reasons Natalie Wood’s performance felt so effortlessly stylish? Her wardrobe was crafted by Edith Head, the legendary costume designer with eight Academy Awards to her name. The sleek, modern outfits became instant fashion inspiration for women in the mid-60s, blending sophistication with a dash of playful rebellion. It wasn’t just costume—it was culture.

More Than Just Romance—It Was a Cultural Bridge

Beneath the fast-paced comedy and love triangle shenanigans, the film hinted at something deeper. Natalie Wood’s character, a young psychologist navigating love and career, represented the new kind of female lead—smart, independent, and not waiting around for a man to define her. It quietly nodded to the coming wave of women’s liberation, packaged in a sugary Hollywood shell.

Conclusion: Why This Movie Still Matters

S*x and the Single Girl might not have delivered Helen Gurley Brown’s book to the screen in a literal sense, but it captured the spirit of a society on the brink of change. It gave us glamor, giggles, and a peek at what Hollywood could be when it dared to flirt with modern ideas. From Natalie Wood’s unexpected casting to Edith Head’s costume brilliance and Tony Curtis’s lovable mischief, this film holds more surprises than you’d think. Rewatch it—not just for the laughs, but for the layers you didn’t see the first time.