In "The Monogamists" (season one), the actor's character gets flirty with Carrie after being introduced by Stanford. Jennifer Aniston's ex also pops up in "Shortcomings" (season two) as a fellow writer named Vaughn Wysel whose relationship with Carrie ultimately falls apart over performance problems in the bedroom.
Fresh off another breakup from Big, Carrie meets Seth Robinson—played by the rocker—in "Games People Play" (season two) in the waiting room of her therapist's office. Sparks fly over a playful game of Twister, but that's about at far as it goes for the pair.
The singer and Carrie lock lips during a game of Spin the Bottle in "Boy, Girl, Boy, Girl..." (season three).
Sarah Jessica Parker's IRL bestie makes a cameo in "Let There Be Light" (season six) as a shoe salesman who helps in Carrie's quest to rid her footwear addiction.
When the Oscar winner (playing himself in season three's "Escape From New York)" pitches an idea to play Big in the movie adaptation of Carrie's life, she is thoroughly weirded out and hightails it far, far away from Los Angeles.
In season three's "Escape From New York," Carrie meets with Debbie, a film exec interested in turning her popular dating column into a movie.
Oh, funky spunk...it's the stinky deal breaker that ultimately led Samantha to call things off with the actor in "Easy Come, Easy Go" (season nine).
In "They Shoot Single People, Don't They?" (season two), Carrie mistakenly poses for a New York Magazine cover titled "Single & Fabulous?" Upset, she seeks solace in the arms of Jake, played by Cooper, who makes a quick exit from their rendezvous when he spots Carrie's face on the mag.
Samantha learns a valuable lesson in "Coulda, Woulda, Shoulda" (season four) when she attempts to jump the waitlist for a Birkin bag by using the actress' name. Oops!
The Arrested Development star lets his freak flag fly in "La Douleur Exquise!" (season two) when he plays Jack, a love interest of Miranda who enjoys having sex in public. All is well until it's revealed that Jack in fact lives at home with his mother, and the excitement fizzles.
While vacationing in Los Angeles in "Sex and Another City" (season three), Carrie is introduced to Keith Travers (Vaughn), who says he's Matt Damon's agent. But things go south when Carrie finds out she actually slept in Carrie Fisher's home...because Keith was merely house sitting.
The Grey's Anatomy star makes a brief appearance in "Anchors Away" (season five) as a police officer who gets in a scuffle with Samantha over flyers.
In "The Real Me" (season four), Carrie meets Alan's character Oscar, a designer who dresses the protagonist in a Dolce & Gabbana ensemble for a fashion show.
Carrie reconnects with her high school sweetheart Jeremy, played by The X: Files star, in "Boy, Interrupted" (season five). Their reunion was short-lived, as her former beau shared he's in a mental institution.
Long before her Pitch Perfect days, the actress appeared in "Politically Erect" (season three) as the significant other of a politician who attends a fundraising party for Carrie's boyfriend.
The late Playboy mogul makes a cameo as himself when the ladies attend a party at the Playboy mansion in "Sex and Another City" (season three). Color Samantha Jones elated.
The Spice Girls superstar made a blink-and-you-missed-it cameo in "Boy, Interrupted" (season six) as an acquaintance of Samantha who waves her exclusive Soho House pool access in her face.
In season four's "Defining Moments," the comedian plays a New Yorker cartoonist named Doug who strikes up a seemingly normal romance with Miranda. Unfortunately, Doug likes to use the restroom with the door open, a major no-no for Cynthia Nixon's titular character.
The iconic Legally Blonde star plays Victoria, a friend who invites the women to a soiree at her home. The get-together turns out to be a purse party featuring her own designs, and the women don't have the heart to tell her she doesn't have a future in fashion.
Long before the actress got her big break in Two Broke Girls, Kat Dennings landed her first role on SATC in "Hot Child in the City" (season three) as a teen who hires Samantha to do PR and book celebrity talent for her Bat Mitzvah.
A fling with the actor, who plays Sam in season one's "Valley of the Twenty-Something Guys," helps Carrie decide she much prefers dating older men after seeing his pigsty of a bachelor pad.