Lea Michelle as Carrie
The point of Carrie Bradshaw is that she is the everywoman. Well, she’s the everywoman who also happens to have a dream job writing a sex column and can somehow afford to live in a big, fancy apartment and buy Manolo Blahnik shoes on a writer’s salary. Blake Lively may be many things, but she’s far too pretty to play your average gal. We prefer Lea Michelle as a young Carrie because she’s nervous, talkative, and, yes, a little bit annoying. She may have to bleach her hair, but she does have the nose for the job. To make it easier for you to imagine the brunette Michelle in the role, we’ve taken the liberty of simulating what she might look like as a Bradshaw blonde.
Evan Rachel Wood as Samantha
We picture young Samantha as precocious, self-confident, and proudly slutty. Evan Rachel Wood is clearly the perfect lady for the job. At only 23 years old, she’s played wild gals since her breakthrough in 2003’s Thirteen. For several years, she had an on-again, off-again relationship with 42-year-old Marilyn Manson (as of last summer, they’re off), which must have helped her grow up fast. And now, in her role as Queen Sophie Anne on True Blood, she’s working the kind of sensual appetite that makes her just perfect to play Ms. Jones.
Leighton Meester as Charlotte
Blair Waldorf may be no prude — although she did manage to hang onto her virginity for a while longer than most of her Gossip Girl pals — but we do see some Charlotte York-Goldenblatt in her. There’s the perfectionism, the prissiness, the fondness for throwing upscale parties. Despite her Texas upbringing, Leighton Meester has the New York WASP archetype down pat, which makes her a great choice to play Charlotte.
Alison Pill as Miranda
Sure, they’ve got red hair in common. But that’s not the only reason we’d cast Alison Pill as Miranda. An ambitious, high-powered lawyer, Miranda is a smart lady. And Pill has excelled in all kinds of serious-young-woman roles, from Harvey Milk’s campaign manager in Milk to art student and lymphoma sufferer April on In Treatment.