Season 1 (1998)
Episode 4: “Valley of the Twenty-Something Guys”
Timothy Olyphant played Sam, who Carrie hooked up with, only to have to ditch him after she realized he lived in not only squalor, but an apartment without toilet paper. Olyphant moved on quickly playing the male lead — Todd Gaines — in “Go” alongside the future Mrs. Tom Cruise — Katie Holmes — and actress-turned-screenwriter extrodinairre Sarah Polley. Olyphant also had parts in “Rock Star” alongside Mark Wahlberg, and a recurring role in HBO’s “Deadwood” as Seth Bullock.
Episode 9: “The Turtle and The Hare”
Sebastian Roche, who now stars and Jerry Jacks on “General Hospital,” made a cameo as another Jerry — a lothario who Samantha met at the wedding of the girls’ pal, Brooke. During their date at Lava, despite telling Samantha he goes after what he wants and looking her deeply in the eyes, Jerry abandons Ms. Jones at the bar for another woman, leaving her to lower her standards and date dragon-breath, “The Turtle.”
Season 2 (1999)
Episode 4: “They Shoot Single People, Don’t They?”
Before starring as Jen Garner’s best friend Will in “Alias,” and taking on roles in “Wedding Crashers” and “Nip/Tuck,” Bradley Cooper played Jake. A dead ringer for Stephen Dorff with shaggy blonde hair, Jake offered a depressed and drunk Carrie a light for her cigarette at a late-night club. Carrie opted to take him home, but when he jumped out of the cab for smokes and cames back with Carrie’s humiliating New York magazine cover with the headline “Single & Fabulous?,” she left him standing in a New York minute.
Episode 6: “The Cheating Curve”
During a gallery exhibition, Charlotte catches her boyfriend cheating and turns to women for support, becoming BFFs with a group of art-buying power-lesbians. “Law & Order: SVU’s” Tamara Tunie played Eileen, one of the gang, who eventually kicked out Charlotte when they found out she was simply looking for female camaraderie and had no intention of going any further.
Episode 8: “The Man, The Myth, The Viagra”
Donald Trump made a cameo, as himself, in one episode of “Sex and The City.” He had a few lines — telling the octogenarian Carlo to call him later at Trump Tower, before exiting the room as Samantha looked on in lust. Her attentions were quickly diverted to Carlo, who attempted to woo her. Things for Samantha didn’t quite work out with Carlo, but Trump’s post-“Sex” life has been fine as he moved on to his own shows — “The Apprentice,” and “The Celebrity Apprentice.”
Episode 11: “Evolution”
John Shea, who played Lex Luthor alongside Teri Hatcher’s Lois Lane and Dean Cain’s Superman in “Lois & Clark: The New Adventures of Superman,” played a baddie in “Sex and The City” as well. For one episode, Shea cropped up as Dominic, the only ex Samantha ever loved, who left her for an Icelandic supermodel. After a chance meeting in a bar on a night out with the girls, Samantha headed home with Dominic hoping to turn the tables and burn him like he did her, only to find him leaving her again following an evening of bedroom activities.
Metrosexual may be the turn of phrase we use these days to refer to straight men who care about grooming, clothing and arts & entertainment, but back in 1999, “Sex and The City” attempted to dub them with the moniker “straight gay man.” Dan Futterman, who later went on to star alongside Angelina Jolie in “A Mighty Heart,” played Stephan, a pastry chef from Chelsea whose highly developed feminine side saw him leap on to the top of a chair after a mouse became trapped on a gluey pad in his kitchen. His leap forced Charlotte to leap back into single-hood. Interestingly, several years after his sexisode, Futterman played Barry, a straight man who realized he was gay later in life on “Will & Grace.”
Episode 12: “La Douleur Exquise!”
Before he became Mr. Amy Poehler, Will Arnett was Mr. Miranda Hobbes for one episode of “Sex and The City.” As Jack, Arnett’s character’s particular quirk was his inability to have coital relations anywhere that wasn’t public. It was the 30-somethings shag back at his parent’s house (where he lived) however, interrupted by his mother and father that forced Miranda to break things off. As for Arnett, he moved on to happier pastures — for three seasons anyway — as Gob Bluth on “Arrested Development.”
Episode 13: “Games People Play”
Jon Bon Jovi played Seth, a very brief romantic interest of Carrie’s. The two met in the office of Carrie’s shrink after her friends told her that continual talk about her breakup with Mr. Big had to be scaled way back. Seth’s reason for seeing a therapist got him quickly written out of Carrie’s life and the show — he admitted he lost interest in women after bedding them. After “Sex,” the rocker went on to play a love interest on “Ally McBeal” two years later. Though his acting roles are sporadic, Bon Jovi can regularly be seen touring the globe with his band.
Episode 14: “The F*** Buddy”
These days Dean Winters is playing Sarah Connor’s boyfriend, Charlie Dixon on the hit Fox show, “Terminator: The Sarah Connor Chronicles.” Before that and before his roles in “Oz,” “Rescue Me” and “30 Rock,” Winter played John McFadden, Carrie Bradshaw’s between the sheets pal. The two had nothing in common except for what they got up to under the covers, leading the sex columnist to break things off altogether.
Episode 15: “Shortcomings”
Golden Globe winner and legendary “Valerie” star Valerie Harper joined the “Sex” cast as Wallis Wysel, the well-traveled, well-spoken, well-written mother of one of Carrie’s flames . Though she quickly decided her beau wasn’t cutting the mustard, or rather, cutting it too soon for her liking, it was a harder decision to break things off with Harper’s character Wallis, with whom Carrie had formed a deep bond.
Episode 17: “Twenty-Something Girls vs Thirty-Something Women”
Enter Bridget Moynahan. Prior to becoming mom to Tom Brady’s only son, Bridget entered the “Sex” picture as Natasha, Mr. Big’s new girlfriend. She was tall, thin and modelesque and a fuzzy-haired Carrie, in a cowboy hat, felt insecure as she encountered the woman for the first time during a break in the Hamptons. Moynahan returned to the series for several more episodes, marrying Big, then divorcing him after his infidelity with Carrie. Before she became a first-time mom last summer, Moynahan followed up her “Sex” life with a role in “I:Robot.”
Episode 18: “Ex And The City”
James Saito now plays Mr. Chen, the man who helps Eli Stone make sense of his visions on the ABC show of the same name, but during Season 2 of “Sex and The City,” he had a cameo as an unnamed flower seller, who Carrie and Miranda attempt to buy flowers from. As Steve Brady comes around a corner, Miranda flips and Saito is forced to holler angrily at the girls who do a runner to avoid an awkward situation with Miranda’s ex.
For more on Matthew McConaughey, Kyle McLaughlin, Sarah Michelle Gellar and more in Season 3, click HERE.
Heidi Klum, Lucy Liu, Ron Rifkin and Candice Bergen joined the cast for “Sex and The City” Season 4. Read about their guest spots and see the photos by clicking HERE.
For more about the appearances of Ron Livingston, Evan Handler, Molly Shannon, Nathan Lane and more of Season 5’s guest stars, click HERE.
And for the guest stars of “Sex and The City’s” final season 6 including Geri Halliwell, Jason Lewis, Blair Underwood and Tatum O’Neal, click HERE.