The Best Guest Stars On Sex And The City

Over 20 years after its 1998 debut, "Sex and the City" is still a cult classic, with its lead, Carrie Bradshaw, remaining one of the most beloved characters on television. With the 2021 premiere of "And Just Like That...," a sequel that picks up with (most) fan-favorite "Sex and the City" characters at their current ages — and the promise of a second season — many fans are reliving their Manhattan socialite dreams by binge watching the raunchy original series.

Throughout its six season run, "Sex and the City" accumulated its fair share of celebrity guest stars and even launched the careers of others. While some were unforgettable, others were easy to miss, even by die-hard "SATC" fans. The recent release of the series on HBO Max has fans scouring for familiar faces. As it turns out, more than a few Hollywood darlings made their mark on the iconic show. 

From Carrie Fisher to Bradley Cooper to Matthew McConaughey, let's take a look at some of the best guest stars on "Sex and the City."

In his first credited acting role, a young Bradley Cooper played Carrie Bradshaw's (Sarah Jessica Parker) 2:00 a.m. hookup. Jake (Cooper) was everything Carrie was looking for at that moment — "single, straight and a smoker." After sharing a passionate kiss in Jake's Porsche, the lovebirds stop to grab some more cigarettes. Just as Carrie is finally beginning to feel young and desirable again, Jake finds her "Single & Fabulous?" New York magazine cover story, forcing her to confront her fading youth and her fear of never finding love.

When asked about his cameo in 2012, Cooper revealed to News24 that kissing Parker was an absolute "nightmare." "I did 'Sex and the City' and I was very nervous because I was driving a stick shift, a standard Porsche, and I thought I was going to bang Sarah Jessica Parker's head against the dashboard. [...] Right before we shot the scene, this guy came up and I think he said, 'SJP does no tongue. No tongue, man'. And I was like, 'Who's SJP?'"

Cooper continued: "So she kisses me, then straddles me in the front of the car and all I kept thinking about was keeping my tongue as far back in my mouth as possible. It was a nightmare. But she wasn't — she was great." Cooper's "SATC" appearance opened many doors for him, and he is now one of the most famous names in Hollywood. Not bad for a 2:00 a.m. hookup!

Best known for her performances in "Kill Bill" and "Charlie's Angels," superstar Lucy Liu played herself in a Season 4 episode, where she hired Samantha Jones (Kim Cattrall) as her PR agent. The episode begins when Samantha spots an Hermès Birkin for the first time and immediately falls in love. A true "material girl," Samantha desperately wants the bag for the status it'd bring. Unfortunately, the Birkin, which was just making its way into the mainstream in 2001, included a five year waiting list. Determined to get her way, Samantha concocts a plan to use Liu's name to purchase the $4,000 bag, causing quite a scene and leaving a bad impression of her client. 

When Samantha and Liu meet again, Samantha is surprised to see that Hermès sent the Birkin directly to Liu. Liu was pretty unhappy that her new publicist cursed out the workers at Hermès so she promptly fires Samantha, taking the Birkin with her.

When asked about her iconic appearance on "Sex and the City" in an interview with Elle, Liu revealed that they didn't even use a real Birkin! "We used a stunt Birkin. The original one was in a safe, and they wouldn't bring it out for us to use until we were filming the scene. It was a very, very special bag. I think it might have had bodyguards." After its iconic cameo, "SATC" is often credited for putting the Birkin on the map.

Former Spice Girl and fashionista Geri Halliwell, aka Ginger Spice, played Phoebe in a Season 6 episode titled "Boy Interrupted." On an impossibly hot August day, Phoebe runs into Samantha Jones and raves about an exclusive pool club called Soho House. Apparently, according to Phoebe, they "mist you with Evian" while members enjoy cocktails and sunshine by the pool. The women part ways and Samantha's demeanor immediately changes. Fueled by jealousy, she decides she'll do anything to get into this club.

This brief encounter prompts our favorite sex-crazed maven to inquire at the Soho House for herself, only to discover that they're no longer accepting members. On her way out, Samantha finds the membership card of an "Annabelle Bronstein" and uses this as her ticket into the club. Soon enough, the employees of the Soho House catch on to her ruse and Samantha is kicked out with what's left of her dignity.

Although short and kind of random, Halliwell's cameo is remembered by fans for her teeny blue bikini, her rock-hard abs, and her over-the-top acting. "Annabelle Bronstein" is also an ongoing meme with "SATC" fans. According to Definition.org, a cameo was also offered to Victoria Beckham, aka Posh Spice, but evidently wasn't possible because filming conflicted with rehearsals for the Spice Girl tour.

Singer and actor Alanis Morissette made a brief cameo in Season 3 of "Sex and the City." Let's set the scene: It's 2000 and Carrie Bradshaw is at a party with her new boyfriend, Mark. Carrie is feeling super out of place. Not only is it a much younger crowd, most of them are LGBT+, including Mark, who is openly bisexual. Mark introduces Carrie to ex-boyfriends, ex-girlfriends, and everything in between while our protagonist hesitantly sucks a cigarette and takes it all in. Surrounded by a medley of sexual orientations, Carrie begins to wonder if gender is a "dying concept." Given the fact that Carrie is a sex columnist, her hesitation in this new environment is quite ironic.

During a game of "Spin The Bottle," Morissette, who played Dawn, lands on Carrie and the two share an awkward kiss before Carrie flees the scene.

In 2014, Morissette reflected on her cameo in an interview with Hollywood.com. She recalled, "I kissed Sarah Jessica Parker. I played a lesbian in 'Sex and the City' and I had to kiss her. I have experimented with same-sex relationships in my life, but it wasn't about enjoyment with Sarah Jessica. Her character was supposed to be reluctant about getting involved, so it wasn't a passionate kiss — it was a reticent one, which is the reason I didn't enjoy it."

In the third season of "SATC," in an episode appropriately titled "Escape from New York," the leading ladies find themselves exploring the streets of sunny Los Angeles. Carrie's "Sex and the City" column has the chance to be adapted into a film, so she travels across the country to meet with the people who could potentially make that happen. Matthew McConaughey played a fictionalized version of himself: An inappropriate, overbearing, and eager producer who had a pretty clear idea of how the Carrie and Mr. Big love story should be told. The two meet in a Warner Bros. Studios office, and McConaughey grills Carrie for details, pushing her to flesh out the "main relationship" of the column. McConaughey's character gives high praises to Mr. Big, claiming he "doesn't know anyone cooler" and Carrie suddenly starts to feel reluctant about the whole thing. Her conversation with McConaughey forces her to question "What about Carrie?" and to examine the role she might've played in her relationship with Mr. Big.

The Hollywood role came naturally to McConaughey, who admitted on The Drew Barrymore Show: "'I don't really remember what I did. I remember I made some strong choices." He continued, "Hewe did take one, the Director/Producer's like, 'Okay. So is that what you are going to do?' And I was like, 'Press record man. That's what I just did. That's who I am. That's what I'm doing.'"

The scene's still hilariously uncomfortable over 20 years later.

In the first episode of the Los Angeles special, Sarah Michelle Geller played Debbie, a talkative junior development executive with a blunt personality.

Debbie wants to help produce the "Sex and the City" film and is not shy about how much she looks up to Carrie. The difference between New Yorkers and Los Angeles natives had never been more obvious than in that moment: Debbie is cool, driven, and over the top, while Carrie comes off as rather quiet and demure. Carrie even describes Debbie as "the most ambitious and feared creature in all of Los Angeles." The two women chat over drinks and Debbie tells her about a producer who is interested in the film: Matthew McConaughey. In that moment, it's obvious that making a movie out of her column was making Carrie uneasy. She shows little excitement and questions why he would even be interested, but still agrees to meet with him at the Warner Bros. Studios.

The two Los Angeles episodes feature a handful of famous faces, but it seems like one didn't quite make it: If you play close attention to their drinks scene, you'll notice that when Debbie whispers Matthew McConaughey's name, her lips actually form the words "Warren Beatty." Presumably, the scene was filmed before Beatty told producers it was "never gonna happen."

Years before playing a Mad Man, John Slattery appeared on two episodes of our favorite raunchy drama, "Where There's Smoke..." and "Politically Erect." In the double feature, Slattery played Bill Kelley, a charming politician who is immediately enamored with Carrie. The two couldn't be more different: One is a primed and prim politician with a carefully curated public image, while the other is a carefree sex columnist with no filter. Somehow, the two are drawn to each other and make some serious eye contact at a FDNY calendar show on Staten Island. Carrie lets slip that she's not registered to vote, and of course, the politician, who is running for New York City comptroller, can't resist the challenge of convincing her to register. The two begin a brief, passionate relationship — a classic case of opposites attract.

Things quickly heat up between the two and soon, they're pillow-talking in Carrie's bed. One day, during a cozy, post-coital chat, Bill asks Carrie if she'll urinate on him. Carrie says she'll think about it, before declining altogether. Bill then dumps her, though he claimed his decision was based on the fact that he can't be associated with a sex columnist, rather than that she won't pee on him. 

Later, Carrie gets her revenge. She writes a column all about a "pissy politician," and — though she graciously didn't name Bill outright in the column — she still gave plenty of clues so readers could connect the dots.

In the Season 2 episode, "Games People Play," Carrie attends therapy to discuss some relationship issues she's been having. In the waiting room, she encounters the handsome Seth (Jon Bon Jovi) and they immediately catch each others' eye. Soon after meeting, the two play a sexy game of Twister and Carrie sleeps with him, finally breaking the ice to ask the one question you probably shouldn't if you're dating someone from your therapist's office: Why was Seth in therapy?

This is when Seth confides that he's seeking help for a toxic pattern of his: He pursues women and immediately loses interest after sex.

Bon Jovi claims to have never watched "Sex and the City" before appearing on the hit show. "I didn't know what 'Sex and the City' was. It was the beginning of the second season and I was not caught up on the first one, so I really didn't know the impact that show was gonna have," he admitted to Entertainment Weekly. "Now when I look back, I go, 'Yeah, I was on 'Sex and the City,' as if I knew, but I really didn't," he added. His excuse? "There's so much television ... doesn't mean I didn't like it, it just went over my head."

A young Kat Dennings appeared in "Hot Child in the City" as the spoiled Jenny Brier, the daughter of a wealthy New York restauranteur who had big plans for her Bat Mitzvah. Jenny hires Samantha Jones as PR for her party, convincing Samantha to take on the "kids party" when she name drops big celebrities like *NSYNC. The spoon-fed teen immediately makes the leading ladies and the audience deeply uncomfortable with her short skirts and overt sexuality. Jenny and her wealthy teenage friends' high maintenance behavior and over-the-top sex talk shocks the usually un-shockable Samantha, who seems to find sadness in their forced maturity.

Having lived a pretty sheltered life, 14-year-old Dennings had no idea what half her sexually loaded lines meant. According to CheatSheet, Dennings admitted she was forced to ask her co-star Kim Cattrall what the phrase "b*** j**" meant, and Cattrall reportedly obliged with a lesson.

Dennings was only featured on one episode of "Sex and the City," but her performance was impressive enough to garner the attention of "2 Broke Girls" creator Michael Patrick King years later. She went on to star as the lead of that show, the hit Hulu show "Dollface," and in multiple Marvel films.

In the Season 4 premiere of "Sex and the City," Carrie runs into Lynne Cameron (Margaret Cho), a highly sought out fashion producer, on a night out with Stanford (Wille Garson). Carrie describes Lynne as "as valuable to a show's success as valium or velcro." The crude producer invites Carrie to model for her latest show, which would feature "a mix of models and New York people with style" — and she doesn't take no for an answer.

Throughout the episode, Carrie questions why Lynne would even want her in the show several times. Each time, Lynne gives Carrie an aggressive pep talk full of profanity to assure her that no one is more New York, or has more style, than Carrie Bradshaw. Heidi Klum also later appears as herself, encouraging Carrie to step out of her comfort zone. When Carrie falls head first on the runway, Klum casually steps over her and Stanford can be heard calling her "fashion roadkill."

Cho, who has experience playing such profane characters, discussed her role with AP Radio (via ABC News): "I curse a mean streak — curse like a sailor. It was very natural to me. The part was written for me, so it was very easy," she revealed. She also said that she has plenty of experience with fashion: "​​I love fashion. I love clothes. [...] I think that my body is a canvas and I feel very excited and thrilled by all kinds of clothing."

In a double guest star episode, Vince Vaughn played a smooth and sexy Hollywood hot shot that helps Carrie and Samantha get into an exclusive Los Angeles afterparty. After a fun night out, Carrie and Vaughn's character, Keith Travers, explore LA together before taking things back to his place to explore each other. It turns out Keith lived in an impressive mansion in the Hollywood Hills, and, the next morning — after a night of love making and cigarette smoking — they are interrupted by none other than Carrie Fisher, who was playing a version of herself. As it turns out, Keith is just her personal assistant, and the large Hollywood Hills house was not his, but Fisher's. Keith was meant to be housesitting, but instead used Fisher's mansion as his own personal bachelor pad.

A naked Carrie Bradshaw tries to defuse the tension by introducing herself ("You're Carrie, I'm Carrie!") but Fisher remains unimpressed. She scolds them for smoking before leaving in a huff, stating she doesn't have time to deal with this because she has a baby (referencing her daughter Billie Lourd) to take care of. 

This double cameo was almost too much to handle and was the perfect ending to Carrie's chaotic Los Angeles adventure.

The late Hugh Hefner never shied away from the spotlight. Throughout his fruitful lifetime, the Playboy founder guest starred on a number of television shows, such as "The Simpsons," "Roseanne," "Entourage," and "Curb Your Enthusiasm." It only makes sense that he also appeared on the raunchiest show of the late '90s, with his Playboy bunnies in tow. 

In an episode judiciously titled "Sex In Another City," the leading ladies find themselves in Los Angeles, where Samantha has the celebrity sighting of her lifetime: None other than sexual icon Hugh Hefner. Samantha introduces herself and Hef invites her to join him and the bunnies for a drink.

"Drinking with three blondes. I guess that's just a regular day for you," Samantha jokes, and Hef responds: "A slow one, yes," with a gleam in his eye. Hefner then invites the girls to a party at the famous Playboy mansion. Eventually, Hefner personally forces the Fab Four to leave, after Samantha accuses someone of stealing her fake Fendi purse.

Best known for his roles in "Arrested Development" and "Bojack Horseman," Will Arnett played Jack, Miranda Hobbes' (Cynthia Nixon) love interest, in a single episode of Season 2. This was one of Arnett's first onscreen roles and introduced him as the funny comedian fans know him as today. 

The episode, titled "La Douleur Exquise!"— French for "exquisite pain" — is all about fetishes and secret, shameful habits, and Miranda's new date seems to have a lot of experience in that area. Although Jack and Miranda appear to have some chemistry, it's only when things heat up in risky, public places that Miranda sees real sparks from him. Eventually, this proves to be a pattern: Jack only wants to have exhibitionist sex and Miranda's not too sure if it's for her.

When it finally seems like Jack is on the same page as Miranda and is willing to meet in an enclosed, private space, the two are evidently caught mid-coitus by Jack's parents. However, the interruption actually seemed to be part of a planned exhibitionist humiliation fetish. Miranda never returns Jack's calls after that.

Carrie Bradshaw ditches a blindfolded Charlotte York (Kristen Davis) in the mall for her new boyfriend and a pair of shoes. The moment her cell phone rings, Carrie excuses herself to go speak with Russian artist and her latest beau, Aleksandr Petrovsky (Mikhail Baryshnikov). While Charlotte gets lost in foot traffic, we see Andy Cohen as a shoe salesman, helping Carrie try on her 10th pair. He doesn't have a line, instead he simply smiles in approval — if you blink you might miss him! Cohen appeared on the show one other time and was uncredited.

"Years ago, I used to beg Sarah Jessica [Parker] to let me run 'Sex and the City' lines with her," Cohen recalled to E! News. "I'd even finagled an audition for a party planner role on 'Sex and the City.'"

Unfortunately for Cohen, Parker was unimpressed by his efforts. "I'll never forget the looks of horror on Sarah Jessica and Hickey's [the director's] faces when I tried to act out a scene for them," he continued. "I didn't get the part." Despite his disastrous audition, Cohen did eventually make it onto a few episodes. "I did play shirtless guy next to Carrie in gay bar in Season 4 and Barneys shoe salesman in Season 6."

In the same episode as Bradley Cooper, "They Shoot Single People, Don't They?" Carrie takes herself out to lunch after a sobering night and makes peace with her "Single and Fabulous?" New York magazine cover story. A young Matthew Morrison waits on her during her meal in what would become his second-ever credited role.

When Sarah Jessica Parker joined the "Glee" cast for an episode in 2012, Morrison shared with Access Hollywood what it was like to work with her years before. "I was 19 years old. I played a bus boy and I think my line was, 'Will anyone else be joining you?' and then I walked away. It was supposed to be at a restaurant, but they shot it [outdoors in] New York," he continued. "The only thing I remember was I walked into this doorway, but the door was closed, so I had to like, tuck into this doorway, but if you look into the reflection you can see my ass, like hanging out, just like trying to be really cool."

Morrison would go on to star in "As The World Turns," "Grey's Anatomy," and of course, "Glee."