ALMOST A YEAR AFTER HE appeared as Samantha's diminutive date, Anthony Alessandro, 37, is still recognized on the street as the guy she dumps after discovering that he shops in the boys' department at Bloomingdale's. "It was like Warhol's '15 minutes,' " says the actor. "I definitely got auditions from it." The show pumped up Eddie Cahill's profile, too. He made his TV debut playing a twentysomething free spirit who takes Carrie ice skating. She is briefly smitten with him—until she finds out he's bisexual. That role led to an upcoming TV pilot as well as spots on Friends and Felicity. "I'm constantly referred to as the ice-skating bisexual," Cahill, 23, says. "My entire life has changed since that episode."
The person responsible for making these men memorable is the show's principal casting director, Jennifer McNamara, a single 33-year-old Manhattanite. Once an episode is written, she rifles through the hundreds of headshots and résumé she receives to find contenders for the speaking parts (197 roles last season). "At first it was hard to explain what the show was," says McNamara—especially when the scripts called for men with bad breath or religious hangups—but once a few episodes had aired "we never had any trouble finding anyone." And even though nudity is often required, McNamara says that doesn't stop as many as 40 actors from filing through the audition rooms for as few as five parts.
It's not just unknowns and up-and-comers who are clamoring to be on the show. The producers are constantly approached by celebrities, "but we don't want to pop somebody on and just point at them," says executive producer Michael Patrick King. "The characters feel real to people—we have to keep it that way." Jon Bon Jovi, Alanis Morissette, Valerie Harper, Vince Vaughn and Sarah Michelle Gellar have all made appearances—and fans like Kate Hudson
are waiting in the wings. "Alec Baldwin is dying to get on the show, but our schedules never, ever click up," says King.
Not every star wants a guest shot, though. King once spied Warren Beatty at a party and persuaded writer and consulting producer Jenny Bicks to ask him to be on an episode. His response? "Never gonna happen."
Notable one-shots are a show hallmark
GAY STRAIGHT GUY
when Dan Futterman—a regular on TV's Judging Amy—auditioned for Charlotte's sexually ambiguous boyfriend, he looked the part. "I came in my most tight-fitting shirt and jumped around screaming when they said 'Now there's a mouse on the floor,' " says the actor, 33. "My wife tells me I play gay well."
Anthony Alessandro—who is 5'5"—says that Kim Cattrall "stood on an apple box and wore 4-inch heels" for his scenes as Jeff, the guy who's small in stature but big on performance.
Real-life firefighter and first-time actor Michael Lombardi, 39, says he was so nervous about his butt-naked performance that he forgot to breathe: "My face turned, like, three different shades of red."
Tim Wheeler says he had "a great time" playing the Turtle, a man with bad breath and worse fashion sense. "I tend to play bad guys and murderers," says Wheeler, 43. "So it was a nice switch."
Celebs get a kick out of playing oddballs
JON BON JOVI
You've got to hand it to the Sex and the City girls. They'll pick up men anywhere—even their therapist's office. Which is exactly where Carrie found Bon Jovi's character in the second season. At the time, the 39-year-old rock star—who cut his acting teeth in 1995's Moonlight and Valentino—"wanted to do more acting work," recalls Sex writer and consulting producer Jenny Bicks. "And the part of the screwed-up guy in the shrink's office was perfect for him. He plays sexy really easily."
An admirer of the show, the Canadian singer called and asked if there was a role for her. There was—as a bisexual who kisses Carrie in a game of Spin the Bottle. Creator Darren Star remembers Morissette, 27, and Sarah Jessica Parker
having fun on set, "breaking out into songs from Annie."
When Carrie et al. went to L.A. last year, McConaughey, 31, played himself—in the guise of a lecherous Hollywood producer. The actor was a good sport. "We were trying to find a celebrity who would be a goof as himself," says Star, "and that's always a touchy situation."
SARAH MICHELLE GELLAR
The 24-year-old star of TV's Buffy the Vampire Slayer says she had fun appearing last season as an over-zealous L.A. movie exec who wants to adapt Carrie's columns for the big screen. "I'm a big fan of the show and was thrilled to be asked on," she says. "I love playing strong characters."
In one episode filmed in L.A., Vaughn, 31, portrayed a pretentious Hollywood player whose real job turns out to be housesitter for Carrie Fisher. On the set, the two guest stars "were hysterical," says Bicks. "At one point Carrie Fisher was spotted wearing a pair of women's panties on her head."