It’s been 21 years since Sex and the City premiered in 1998 and fans are still rewatching the stylish and witty four best friends get through life, dating, and living in NYC.
Sex and the City may have made a star out of Sarah Jessica Parker and helped prove that women’s stories deserved to be told, but it also featured some talented guest stars. While you might not have taken note of the celebs the first time around, you would definitely notice some of them if you embarked on a big rewatch of the show. Since the show is about love, sex, and relationships and there are four main characters who are in the dating world, there are a lot of guest stars.
Here are some of the best guest stars on Sex and the City, ranked.
Dean Winters
In the pilot, Carrie wonders if she can “have sex like a man” and she hooks up with a character named Kurt (Bill Sage). In the second season, Dean Winters appears as John, a character she has a casual thing with. Many storylines on TV shows and in movies revolve around whether men and women can simply be friends with benefits and this is a similar situation.
While he’s not as famous as some of the other guest stars who have been on the show, he’s a good addition. Dean Winters has also starred on Oz, Rescue Me, and as Detective Keith Pembroke (also known as “The Vulture”) in a few episodes of Brooklyn Nine-Nine. And, of course, he was Dennis Duffy on 30 Rock.
Kat Dennings
You know Kat Dennings from starring on 2 Broke Girls, which aired from 2011 until 2017, along with roles in movies like Nick and Norah’s Infinite Playlist and Raise Your Voice. She also had a guest starring role on Sex and the City.
One amazing aspect of SATC is the fact that it focused on the women’s jobs. Besides Carrie’s regular relationship column, Samantha ran her own business, and that’s why Kat Dennings appeared in this episode. She played Jenny in the season three episode “Hot Child in the City.” Samantha is working on her Bat Mitzvah. She’s known for saying, “I didn’t know you knew Carrie Bradshaw!” It’s pretty adorable.
Elizabeth Banks
In terms of really famous actresses who guest starred on Sex and the City, Elizabeth Banks is definitely at the top. She has made a name for herself with the Pitch Perfect films: she played Gail Abernathy-McKadden in the first two movies, produced them, and also directed the second outing. She’s a cheerful staple in any movie or TV show that she stars in, and she has also appeared in many episodes of 30 Rock and Modern Family.
She was on Sex and the City as Catherine in the third season episode “Politically Erect.” All that happens is Charlotte is having a discussion with Catherine’s husband and Catherine comes over.
Sure, this is a really brief moment – but since Elizabeth Banks is so famous now, it’s a fun guest star role to think about.
Jim Gaffigan
Did you know that Jim Gaffigan was on Sex and the City? Maybe not, but it’s definitely a fun fact.
The hilarious comedian guest starred in a season four episode called “Defining Moments” and played a guy who dates Miranda and had one annoying habit that she can’t stand: not needing any privacy when he used the bathroom. She doesn’t want to see him use the toilet and, honestly, who can blame her for that?
This was an awesome guest starring role since if there’s one thing that fans love about SATC, it’s watching the four women go on bad dates. Miranda, in particular, is known for picking out flaws, so this was memorable.
Alanis Morisette
The singer deserves a spot on this list ranking the guest stars on Sex and the City as she and Carrie kiss at a party, which fans will remember for sure. It’s not ranked higher as this is a brief appearance but it’s worth pointing out. Her appearance is in the season three episode called “Boy, Girl, Boy, Girl…”
Carrie kisses her character during Spin the Bottle. Of the kiss, Alanis has been quoted as saying, " “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.”
Timothy Olyphant
Remember when Carrie was in a relationship with a guy in his 20s? Timothy Olyphant played this character, and it’s one of the best minor roles on the show, which is why it’s ranked at number three.
The Santa Clarita Diet actor played Sam, a guy who was intriguing to Carrie… but then she discovered how completely messy he was. Okay, messy would be putting it lightly. The guy is a total slob, and he doesn’t seem to care at all. Fans could definitely tell her that she needs to be with someone who is much more mature (and probably older). It wasn’t Carrie’s best relationship… but the guest-starring role was perfect.
John Slattery
The Mad Men star had a guest role on Sex and the City and even if you didn’t realize that it was him, you probably can recall the awkward scene: his character, Bill Kelley, hooks up with Carrie… and then says that it would be great if she, um, urinated on him while they were taking a shower. The fact that he was working in politics? That made it even weirder.
If you want to go back and see this, it was in the season three episode called “Politically Erect.”
John Slattery takes the number two spot on this list ranking some of the best guest stars on the show because this was a guest-starring role to remember. It’s one of the iconic moments from the show since it speaks to one of the major themes: the women standing up for themselves and dealing with the truly weird New York dating scene.
Bradley Cooper
Bradley Cooper just finished an epic Oscars season where he was praised for his acting and directing work in A Star Is Born. Before that, of course, he has starred in several movies.
He’s one of Hollywood’s biggest celebrities, but before that, he actually was in an episode of Sex and the City. The actor appears in the second season episode called “They Shoot Single People, Don’t They?” Carrie has just realized that her big moment – being on the cover of a magazine – has turned into a disaster when she learns that the cover line says “Single and Fabulous?” The question mark at the end is getting to her. Carrie drinks too much and comes across Bradley’s character, Jake. He’s the best guest star on the show, hands down, which makes it number one on this list.
Jake is one of the most well-known minor characters on Sex and the City, and it’s worth checking this scene out again to see a really young Bradley Cooper.
