Slattery has become a major star as Roger Sterling on Mad Men. However, before he was seducing women throughout the 1960s, he took advantage of Carrie Bradshaw’s daddy issues as New York politician Bill Kelley in a two-episode arc “Politically Erect” and “Where There’s Smoke.” Sadly, things didn’t work out: he liked water sports and Carrie didn’t have time for that.
Before 2 Broke Girls, Dennings played one rich girl, Jenny Brier, who was a client of Samantha Jones. She was so sexually aggressive it even shocked Samantha. It’s hard to imagine a pint-sized Dennings, but check out “Hot Child in the City.”
Coolidge is another 2 Broke Girls regular that starred on Sex and the City. Fresh from her American Pie fame, Coolidge played a Real Housewife type who decides to design handbags. Sadly, Samantha ruins her party by having sex with a waiter.
Theroux was a two-time guest on SATC. Before he was Jennifer Aniston’s man with the perfect abs, he was Carrie’s man with the perfect family. He was a writer with sex issues who had such a dynamic family with whom Miss Bradshaw decided to try and make it work in “Shortcomings.” He also had a few lines in “The Monogamists” as a flirty writer, oddly.
Not only was Banks on Sex and the City, but she was in the same episode as John Slattery. She had a couple of lines as a political girlfriend type in “Politically Erect.” You never know who will go from small role to big star. Is this the origin of Avery Jessup?
Olyphant is best known for darker roles on Justified and Deadwood, so it’s funny to think that one of his early roles was as Carrie’s latest addiction. In “Valley of the Twenty-Something Guys,” the girls all find themselves with guys in their twenties. He wasn’t a huge star, but he was a big enough star that they used a double when his character Sam flashes a tongue ring.
Cannavale has brought some major sex appeal to television. It started as one of Samantha’s numerous lovers, Adam Ball, the “funky spunk” guy. He was an intense businessman who inhabited Samantha’s Island of Misfit Guys for his role in episode “Easy Come, Easy Go.”
McConaughey as Mr. Big? For a brief second, Carrie was considering a movie version of her column. The famous actor, not an Oscar-winner yet, was in talks to play Mr. Big. The two flirted but it didn’t go anywhere and Carrie’s love for L.A. faded fast.
GOB Bluth was a bit of a kinkster, but Arnett also played Miranda’s kinky boyfriend in the episode “La Douleur Exquise!” He was obsessed with getting caught until, as expected, it became too much. It’s almost hard to imagine such a huge comedy star in such a small role on the show.
Cooper’s acting career seems like a “how to” guy. He famously appeared on Inside the Actor’s Studio as a student then a guest. His first acting role was as a hot guy who picks up a drunk Carrie at a bar in “They Shoot Single People, Don't They?” Sadly, Jake didn’t take her home because she was too heartbroken over an embarrassing magazine cover.