A society staple, Calicchio is heir to one of New York's biggest real estate fortunes.

Charlie Rangel is the gravelly-voiced Congressman who represents Harlem, Spanish Harlem, and Washington Heights. Of course, you probably know him best for his near-constant appearances on the cable news circuit.

A prominent Democratic consultant and the founder of the political consultancy Sheinkopf Communications, Hank has worked on campaigns for Bill Clinton, Betsy Gotbaum, Mark Green, Eliot Spitzer, and Bill Thompson, among many others. He's also a prolific talking head and staple on local political news programs.

Actress Mariska Hargitay plays uptight detective Olivia Benson on Law & Order: Special Victims Unit.

Gina Gershon is the pillow-lipped actress known for playing sexy lesbians and femme fatales in movies like Bound and Showgirls. Gershon grew up in Los Angeles and moved east after high school, attending Emerson College in Boston before transferring to NYU. Her first big movie role came in 1988 when she was cast in Cocktail with Tom Cruise. More than a dozen films followed during the '90s, although none ever quite earned her A-list status in Hollywood. In recent years, she's appeared on Broadway (as Sally Bowles in Cabaret, Rosie Alvarez in Bye Bye, Birdie, and Gabriella in Boeing-Boeing), in a handful of indie films, and on a number of television shows (including Curb Your Enthusiasm and How to Make it in America). In addition to her acting credits, Gershon's also written a children's book with her brother and played Jew's Harp on songs by Rufus Wainwright, the Scissor Sisters, and Herbie Hancock, among others. A Vanity Fair rumor suggested she'd had a brief fling with President Bill Clinton in 2008, but little evidence supported it (though she is, despite her notable queer-leaning roles, straight-identified).

Thanks to roles in geek fare like Star Wars, V for Vendetta, and Garden State, the former child actress from Long Island is what Winona Ryder was a generation ago-a perpetually pixified princess with an edge.

Rosie is the genial talk show host-turned-loudmouthed dyke.

The doughy Hoffman made his name as a quintessential actor's actor in a slew of indies, although of late he's spent more of his time cashing in on his cred with roles in mainstream Hollywood productions.

DeWoody is a socialite, art collector and scion of the Rudin family, the NYC real estate clan that owns dozens of office and apartment buildings in Manhattan.

The buxom star of such films as Lost in Translation and Ghost World, as of late Johansson alternates between Woody Allen muse and mainstream action hero.

Calvin Klein was arguably America's first rock star designer. He grew up in the Bronx, sketching designs as a kid, then kept up his interest in fashion as a student at High School of Art and Design, later heading off to FIT. His first break came when a buyer from Bonwit Teller, getting off an elevator at a wrong floor, stumbled upon Klein's start-up showroom of a dozen or so samples—a meeting that landed Klein a $50,000 order. From there, Klein produced his first sportswear collection in 1973, a jeans line in the late '70s, and a menswear collection soon following. He struck a number of licensing deals in the '80s, creating buzz with a series of racy commercials to promote them. The success of Klein's underwear line, combined with the peak of the designer-jeans fad, brought huge revenues to the company in the late '80s. However, the company suffered a number of financial problems in the recession of the early-'90s, nearly filing for bankruptcy before being bailed out by Klein's buddy David Geffen. The later '90s saw a return to profitability, particularly after the introduction of CK, a lower-priced, youth-oriented line. In 2002, Klein sold the brand to Phillips-Van Heusen, effectively divorcing himself from his company, though he remains a prominent figure in the fashion world still. He has kept a complicated personal life along the way, marrying twice to two women yet also having numerous semi-public relationships with men (younger male models in particular). He and his first wife had a daughter, Marci Klein, who's now a TV producer at Saturday Night Life.

The once pudgy and quirky hipster, Marc Jacobs is at the very top of the fashion biz.

Fashion icon Karan no longer owns the company that bears her name, having sold out for $643 million in 2001, but she remains creative director.

As mob chieftain Tony Soprano-the role in which he will forever be frozen-the bearish Gandolfini became both an iconic tough guy and a heartthrob for chubby-chasers.

Despite some mediocre movies, Danes is best known and praised for her work on television, particularly as teen angst icon Angela Chase. She also has found herself embroiled in a series of tabloid-worthy romances.

Terry Allen Kramer

Nerd pinup Tina Fey has presided over Saturday Night Live as head writer and now stars on the NBC sitcom 30 Rock.

Julia Stiles in the moon-faced, precocious young actress known for starring in a spate of teen romance flicks in the late '90s. She'd now like to be considered a serious actor, thank you very much.

Former SNL cast member Jimmy Fallon has managed to rocket to pop culture ubiquity and earn one of the most coveted jobs in late-night TV.

A fixture on the downtown scene since the 1970s, McDonald is the dandy who is impossible to miss thanks to his wild outfits, costume jewelry, jaunty hats, and meticulously applied make-up. He's also dabbled with reality TV. In 2009-10, he was a contestant on the Bravo show Launch My Line.