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!

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.

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.

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.

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 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.

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.

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."