Drama Lived Here
If there’s a show that packs drama into every minute, it’s Sex and the City. And along with all that chaos came celebrities, many of whom were unforgettable, with their quirks that we loved to judge.
Tatum O’Neal Tried To Brag About Her Baby’s Firsts
Charlotte runs into smug, status-obsessed Kyra at a baby shower. When Carrie’s pricey shoes vanish, Kyra refuses to pay, hinting that single women’s lives lack value. The episode sharply critiques how motherhood can become a moral pedestal in social hierarchies among women.
SATC a woman's right to shoes - phone call by Power University
Bradley Cooper Took Carrie On A Wild Magazine Cover Ride
Before his role in Wet Hot American Summer (2000), Cooper played Jake—the guy who flirted with Carrie outside a bar and ended up discovering her infamous “Single and Fabulous?” magazine cover. Remember that Karmann Ghia? Classic cringe. He ghosted fast, but the impact? Unforgettable.
S2E04 Clip | Bradley Cooper and the City by SEX AND THE CITY 𝓐𝓻𝓬𝓱𝓲𝓿𝓮𝓼
Justin Theroux Played Two Different Men In Separate Episodes
Twice the face, zero continuity. Theroux showed up once as a writer named Jared, then returned as Vaughn Wysel, a short-story writer with premature problems. Both failed to win Carrie’s heart, but he definitely earned a place in SATC trivia history.
Top 10 Celebs Who Were on Sex and the City Before They Were Famous by MsMojo
Jon Bon Jovi Confessed To Dating In Therapy
Sitting beside Carrie in a waiting room, Bon Jovi's Seth turned out to be dangerously charming, until he casually confessed he dated women, lost interest, then ghosted. That revelation? Delivered with a smirk. Plot twist: Carrie was seeing the therapist as a patient after her breakup with Big.
Jon Bon Jovi on "Sex And The City" part 1 by aviya1
Matthew McConaughey Wanted To Play Mr Big In A Movie
Channeling Hollywood weird, McConaughey pitched himself to play Big in a potential movie adaptation of Carrie’s column. At a bizarre meeting, he flirted, rambled, and somehow made it all feel real. “Let’s make this movie,” he said. Thank heavens they didn’t.
Top 10 Actors You Forgot Were on Sex and the City by MsMojo
Elizabeth Banks Crashed Charlotte’s Love Life With Class
Before ruling comedy, Banks briefly dazzled as Catherine, the elegant fiancee of Charlotte’s latest crush. At a political fundraiser, she gracefully revealed they met at a “cast-off” party, where women brought men they weren’t interested in. Subtle, composed, and sharper than expected, her scene-stealing moment inspired Charlotte’s next dating experiment.
Top 10 Celebs Who Were on Sex and the City Before They Were Famous by MsMojo
Geri Halliwell Invited Samantha To Soho House’s Pool
Spice Girl in the mix. Geri’s cameo as Phoebe was short but oh-so-sassy. Geri Halliwell’s Phoebe mentioned the Soho House pool, leading Samantha to use a found membership card. Sam showed up, soaked up luxury, then quickly got banned. Poolside drama? Served.
Geri Halliwell - SEX AND THE CITY - Cameo by Licho's Video Collection
Vince Vaughn Pretended To Be A Hollywood Agent
He wasn’t repping Matt Damon—he just played like he was. Vaughn’s Keith duped Carrie during her LA trip, giving off slick charm until his real identity surfaced. Turns out, he was just a personal assistant with a taste for fantasy and fast talk.
Top 10 Actors You Forgot Were on Sex and the City by MsMojo
Kat Dennings Was A Teenage Socialite With Big Demands
Before she ruled on 2 Broke Girls, Dennings played Jenny Brier, a bratty bat mitzvah-bound teen who hired Samantha to plan her party. The twist? Jenny blackmailed Sam into inviting celebs. Her attitude was pure Upper East Side with a diamond-studded cherry on top.
Top 10 Celebs Who Were on Sex and the City Before They Were Famous by MsMojo
Alanis Morissette Kissed Carrie In A Game Of Spin The Bottle
What happens at a party stays on cable TV—unless it’s Carrie kissing Alanis. Yep, Morissette made a one-scene splash as a bisexual woman in a game of spin the bottle. The kiss: “It wasn’t bad, kind of like chicken,” Carrie said, and the moment still replayed at brunches everywhere.
S^x and the City - Carrie Bradshaw first time kissing a girl - S3E4 by Vex19
Jennifer Coolidge Threw A Purse Party Nobody Wanted
Coolidge’s cameo as social outcast Victoria was a gift, if only her handbags were. She hosted a purse party, hoping to wow the girls, but the designs? Think spaghetti straps and glitter explosions. Victoria angrily demanded the girls leave after they criticized her designs.
Timothy Olyphant Was Carrie’s Too-Young Flirtation
He rocked a skateboard, messy hair, and a studio filled with incense. Olyphant’s character brought college-level chaos into Carrie’s polished world. Things crashed when she saw his habits—like unwashed dishes and retro posters—as major turnoffs. It turns out that the generation gap can’t be accessorized.
Timothy Oliphant - Sam -Sex and the City S1E4 Valley of the Twenty-Something Guys (1998) by S Rubi
Will Arnett Took Miranda’s Kink To The Next Level
His character had one very specific fantasy—public exposure. Miranda, skeptical but curious, played along until neighbors got too close. What started as edgy turned awkward. Arnett's intensity made it unforgettable, even if it ended with a firmly closed door and zero repeat visits.
Top 10 Actors You Forgot Were on Sex and the City by MsMojo
David Duchovny Was Carrie’s High School Flame In Therapy
They reconnected at a psychiatric facility, where he was a patient, and Carrie was visiting to explore a romantic reunion with Jeremy. Things seemed sweetly nostalgic until Carrie realized his residency was ongoing. Their emotional spark fizzled out when reality intervened. A brief reunion, beautifully strange, and undeniably bittersweet.
Top 10 Actors You Forgot Were on Sex and the City by MsMojo
Gabriel Macht Filmed Models—and Tried to Seduce Samantha
Before Suits, Macht played Barkley, an artist with a risque hobby: secretly taping his hookups with models. When Carrie spills the tea, Samantha doesn’t flinch, but flirts. What follows was a game of seduction, voyeurism, and vintage SATC scandal. Bold and totally on-brand for 1998.
Top 10 Celebs Who Were on Sex and the City Before They Were Famous by MsMojo
Sarah Michelle Gellar Pitched A Film Deal To Carrie
In full Hollywood exec mode, Gellar played an over-caffeinated producer eager to turn Carrie’s column into cinema. She rattled off dream castings and buzzwords, dazzling and dizzying all at once. The deal never happened, but her high-speed charm lingered long after.
Top 10 Actors You Forgot Were on Sex and the City by MsMojo
The Current US President Appeared As Himself At A Party Scene
He didn’t need a script; he just walked through a posh gathering being, well, himself. His presence added a dose of real-world Manhattan elite to the show’s glamor. It was blink-and-you’ll-miss-it, but completely in line with the city’s flashy, fame-driven backdrop.
Olivier Duquesne, Wikimedia Commons
Lucy Liu Fired Samantha Over A Fake Birkin Scandal
Samantha name-dropped Liu to snag an exclusive designer handbag, and it backfired in public. When Liu found out, she ended their working relationship on the spot. The fallout was swift, stylish, and a sharp lesson in the limits of name-dropping in fashion circles.
SATC HD | Lucy Liu Fires Samantha Jones | [HD] by SEX AND THE CITY 𝓐𝓻𝓬hives
Margaret Cho Cast Carrie In A Fashion Show
Playing an ambitious showrunner, Cho tapped Carrie to walk the runway in an edgy designer event. Her energy pushed Carrie into unfamiliar territory, surrounded by models and flashbulbs. Carrie’s catwalk crash became iconic, but Cho’s infectious enthusiasm kept the chaos entertaining.
Margaret Cho in Sex and the City by 0dour
Heidi Klum Modeled Down The Runway With Carrie
Towering, flawless, and unbothered, Klum played herself in the same fashion show where Carrie’s heel caught the runway. As Carrie tumbled, Klum floated past in couture, making it look effortless. The moment became a visual metaphor for fashion hierarchy in motion.
Blair Underwood Was Miranda’s Handsome Doctor Boyfriend
As a successful surgeon and sweet neighbor, Underwood’s character, Robert, offered Miranda romance and stability. He even moved into her building and built a genuine connection. Everything seemed ideal—until her unresolved feelings for Steve resurfaced. His role left viewers torn between comfort and history.
![SATC | Miranda vs Everybody Else | [HD]](https://www.factinate.com/storage/app/media/theshot/2025/7/7/5-7.jpg)
SATC | Miranda vs Everybody Else | [HD] by SEX AND THE CITY 𝓐𝓻𝓬𝓱𝓲𝓿𝓮𝓼
Bobby Cannavale Was “Mr Funky Spunk”—And Yes, That’s Canon
As Adam Ball, Cannavale played one of Samantha’s many one-episode flings, memorable for all the wrong reasons. Despite his charm, things got awkward fast in Season 3’s “Easy Come, Easy Go”. Let’s just say the nickname “Mr Funky Spunk” wasn’t earned for his personality. Second date material? Not even close.
Top 10 Celebs Who Were on Sex and the City Before They Were Famous by MsMojo
Kristen Johnston Fell Out Of A Window After A Monolog
In one of the show’s darkest, most absurd turns, Johnston played a fading party girl clinging to Manhattan’s social scene. After defending her lifestyle on a balcony ledge, she dramatically fell to her death. The moment blended satire, tragedy, and unforgettable commentary on aging nightlife.
Lexi Featherston by Bike, Beats, and Bumpy Streets
Ron Livingston Played Carrie's Infamously Post-It Ex
Livingston brought smug energy as Jack Berger, a fellow writer who couldn’t handle Carrie’s success. Their relationship crashed when he dumped her with a Post-it. No speech, no goodbye—just sticky stationery. That move became iconic, spawning memes and brunch rants for decades.
Top 10 Memorable Sex And The City Boyfriends by MsMojo
Nathan Lane Married Bitsy in a Lavish Ceremony
He appeared as Bobby Fine, a flamboyant piano player who shocked everyone by marrying Bitsy Von Muffling. The wedding sparked gossip and a crisis of commitment for Charlotte. Lane’s flair lit up the Hamptons, even if the union raised more eyebrows than champagne glasses.
Carrie Fisher Had A Scene With Sarah Jessica Parker Playing Herself
In a twisty LA storyline, Carrie Fisher played a version of herself, discovering that Parker’s character was staying in her house with a barely clothed assistant. Things turned awkward fast. The moment doubled as fan service and meta madness—two worlds colliding over lost lingerie.
John Slattery Wanted Carrie To Try Water Sports—Literally
As a charismatic politician in Season 3, Slattery wooed Carrie with charm and ambition. But behind closed doors, he had one particular—and wet—request. Carrie wasn’t up for it, and things dried up fast. The episode balanced shock and satire, and it made his cameo unforgettable, if slightly off-putting.
Top 10 Celebs Who Were on Sex and the City Before They Were Famous by MsMojo
Michael Showalter Played Billy, Who Met Carrie At A Night Club
Michael Showalter’s Billy met Carrie at a nightclub in Season 6, Episode 4, “The Post-It Always Sticks Twice,” where she vented about her breakup. His awkward charm clashed with her raw frustration, leading to a sharp dismissal that underscored her emotional turmoil and the absurdity of rebound encounters.
Neil Grabowsky, Wikimedia Commons
Peter Hermann Played A Gorgeous But Inattentive Date
Tall, handsome, and impressively blank—Hermann's character looked like perfection but showed no real interest in Carrie beyond appearances. The conversation went nowhere fast, and the chemistry? Nonexistent. His beauty might’ve turned heads, but his personality left absolutely nothing to hold onto.
Sex and the City "Hop, Skip, and a Week" Peter Hermann by TM
Kyle MacLachlan Was Charlotte’s WASP-y, Mommy-Fixated Husband
MacLachlan’s Trey seemed like the perfect Upper East Side catch, handsome and wealthy. But his deep attachment to his controlling mother made intimacy impossible. Between his bedroom issues and Bunny’s interference, Charlotte’s dream marriage turned into a blueprint for buttoned-up dysfunction.
Top 10 Memorable Sex And The City Boyfriends by MsMojo
Mikhail Baryshnikov Danced Into Carrie’s Heart As Aleksandr Petrovsky
Baryshnikov brought sophistication, art, and Parisian flair. As Petrovsky and Baryshnikov swept Carrie into a whirlwind romance, it relocated her to Paris. But the fairy tale faded, revealing coldness behind the elegance. Fans still debate the relationship, but his presence reshaped the final arc.
Top 10 Memorable Sex And The City Boyfriends by MsMojo
Chris Payne Gilbert Slept In Charlotte’s Guest Room—Then More
Gordon is a charming and attractive man from House & Garden magazine. He visits Charlotte’s apartment to photograph her and Trey for a feature. At this point, Charlotte’s marriage is unravelling, and the shoot becomes emotionally charged. While he doesn’t play a long-term love interest, his presence adds to the tension.
Beau Garrett & Boyfriend Chris Payne Gilbert at "Commerce" Premiere by Maximotv
James Remar Appeared As Richard, Samantha’s Boyfriend, A Hotel Executive
As a slick hotel executive, Remar slid into Richard Wright’s world and oozed confidence. Samantha sized him up quickly and passed. His interactions hinted at power plays and hidden agendas, matching the show's recurring theme: behind every luxury suite is a shady deal.
Top 10 Memorable Sex And The City Boyfriends by MsMojo
Craig Bierko Played A Jazz Musician Who Couldn’t Stop Playing
The guy oozed charm and saxophone riffs. Carrie was into his rhythm until she realized the music never stopped, even during intimate moments. Every scene came with background brass. Then, the vibe turned from sexy to surreal, and she left before the next set started.
SATC | Season 4 | Episode 3 | Ray King by SEX AND THE CITY 𝓐𝓻𝓬𝓱𝓲𝓿𝓮𝓼
Daniel Sunjata Was A Sailor Looking For A Good Time
Dressed in crisp whites and all smiles, Sunjata played a visiting naval officer on shore leave. His charm instantly caught Samantha’s eye, and that led to a night of spontaneous fun. The uniform dazzled, the chemistry sparked, and the exit was swift, just like the fleet.
David Alan Basche Got Dumped for Wearing Socks In Bed
Everything seemed fine—until Basche, playing David, slipped under the covers. Those socks? Deal breaker. Carrie couldn’t unsee it, and the relationship unraveled with one bedtime faux pas. The moment became legendary, proving that sometimes the smallest details make the biggest impact in dating.
Inside The Exes Studio: David Alan Basche by TV Land
Dean Winters Was Miranda’s Ex With Bad Timing
Winters played Tom, a guy Miranda had once dated and awkwardly ran into again. They gave it another shot, but his lack of maturity and direction stood out. The second time wasn’t the charm—it was a gentle reminder that some doors should stay shut.
Peter Massas, Wikimedia Commons
Mario Cantone Became Charlotte’s Outspoken Wedding Planner
As Anthony Marentino, Cantone delivered biting wit, bold fashion opinions, and zero patience for indecisiveness. Marentino clashed with everyone except Charlotte, eventually becoming her trusted ally. His one-liners hit hard, and his presence brought fabulous chaos to every bridal scene he touched.
And Just Like That | Anthony schools Rock | HBO Max | S01E10 by SEX AND THE CITY 𝓐𝓻𝓬hives
Wallace Langham Had A Shocking Foot Obsession Surprise
Things take a turn when Josh reveals a strong foot obsession. At first, Charlotte tries to be open-minded, but it quickly escalates. He offers to buy her expensive designer shoes in exchange for time with her feet, crossing a line from quirky to transactional. Charlotte ultimately walks away—heels in hand.
vagueonthehow, Wikimedia Commons
Julie Halston Played Bitsybitsy Von Muffling, A Socialite, In A Key Social Scene
During Bitsy Von Muffling’s Hamptons wedding, Halston’s character floated through the background with over-the-top elegance and deadpan delivery. She brought peak New York socialite energy, and she anchored the party’s absurdity. Her limited screen time delivered just enough sparkle to leave an impression.
SATC | Bitsy Von Muffling vs Mrs. Goldenblatt by SEX AND THE CITY 𝓐𝓻𝓬𝓱𝓲𝓿𝓮𝓼
Caroline Aaron Was Charlotte’s Blunt Fertility Counselor
When Aaron showed up, she played a fertility expert who delivered bad news with clinical precision. She would constantly make dramatic shifts on Charlotte’s arc, replacing hope with hard facts. In one short scene, she shattered illusions and spotlighted real-world heartbreak inside a show better known for fantasy.
Chatting with character actor Caroline Aaron by KING 5 Seattle
Jim Gaffigan Played Miranda’s Date With Bathroom Boundaries Issues
Gaffigan’s character started strong, until he refused to shut the door while using the bathroom. Miranda, appalled, tried to overlook it but couldn’t unhear the details. The situation spiraled from mildly gross to full-on dealbreaker. Some relationships end with a bang—others with a flush.
Amy Sedaris Was A Book Publicist On A Deadline Bender
Courtney Masterson wasn’t just loud—she was literary chaos in designer heels. Played by Amy Sedaris, this jittery book publicist hurled Carrie into publishing with rapid-fire pitches and high-stakes energy. She even introduced her to Jack Berger. Between deadlines and drama, Courtney made business meetings feel like caffeine-fueled therapy.
SATC HD | The Sex And The City Book | [HD] by SEX AND THE CITY 𝓐𝓻𝓬hives
Molly Shannon Played Lily Martin, Carrie’s Book Agent
Molly Shannon played Lily Martin, Carrie Bradshaw’s spirited book agent. With her signature comedic flair, Lily was assertive, fast-talking, and business-savvy, pushing Carrie toward deadlines while traversing the publishing world with a mix of charm and publishing-world pragmatism.
