Gossiping Hulton Archive/George Marks
By Amy Phillips Penn

VINTAGE GOSSIP is alive and well in the elegant hands of Amy Phillips Penn, former society columnist for the New York Post.  Every Thursday, Amy pens her posts with that same touch of class, making the legends and lore of a bygone era as relevant today as they were when Jackie O was queen of New York.

William Miller: Well, it was fun.
Lester Bangs: They make you feel cool. And hey. I met you. You are not cool.
William Miller: I know. Even when I thought I was, I knew I wasn’t.
Lester Bangs: That’s because we’re uncool. And while women will always be a problem for us, most of the great art in the world is about that very same problem. Good-looking people don’t have any spine. Their art never lasts. They get the girls, but we’re smarter.
William Miller: I’m glad you were home.
Lester Bangs: I’m always home. I’m uncool.
William Miller: Me too!

Almost Famous

Being cool was big in the ’60s.

Cool was a smoke ring of “aloof meets do not disturb.”

If you were cool, you hung out with other cool people. Cool clearly ices out warm and fuzzy. If you yearned to be in a cool clique, you needed to drop a few degrees, and freeze on down the road.

Cliques sprout their “I’m so cool” little heads everywhere. There are family cliques, school cliques — starting from nursery (ouch) — club cliques, “My family came over on the Mayflower” cliques, neighborhood cliques, and the monied cliques of those who spend together and trend together.

My niece, upon entering a new nursery school, announced, “I have one friend. Her name is Maggie. She is the only friend I have, and the only friend I need.”

When I was at Town School for my younger years, the “in” clique was defined more by exclusion that inclusion. There were two girls who someone deemed as outsiders, and they were treated as such. The rest of us formed a clique by default.  It wasn’t as if we thought that we were cool (we weren’t); it was that they just weren’t “us.”

We were delivered home in a school bus in the shape of a station wagon. When we dropped off one of the “uncool” girls at her home, her mother came to the car carrying a tree branch.

“If you’re ever mean to my child again, I will beat you with this,” she announced to the rest of us.

When I moved on to Hewitt’s, I quickly became close friends with a Gidget-gone-blonde girl named Wendy. We were BFF’s for the long term. Our yearbooks reinforced our devotion to each other: my senior page includes “Lost without Wendy,” while hers commits to “Lost without Amy.”

While we were best friends and usually hung out with two or three other close friends, there was no sense of snobbery or exclusion. Cliques seemed to form in an organic way and stayed velcroed together by a comfortable consent. If your usual entourage was not available to sit with at lunch, you were welcome anywhere else.

There are some people who defy the need for a clique. They are often the diameter of a clique waiting to be formed around their cool front. These girls stand out and know it.

At the start of a new year at Hewitt’s, we were all in our plaid skirts and blazers, while an attractive girl in a geometrical Sassoon haircut and a Pucci print dress, toured the school with the assistant headmistress. Pucci and Sassoon aside, she wore the famous last name of a Broadway composer.

She looked us over for a few days, and then enrolled in Dalton.

She wouldn’t need a clique to cling on to there; she was more likely to have her own followers (think Gossip Girl meets the ’60s).

When I went on to college, there were around 10 freshman girls in our dorm. We roomed together for the rest of our years. Only one girl went M.I.A. She was asked to go her own way, as she was thought to be too mean and destructive to include.

Later on, cliques seemed irrelevant.

One of my favorite interviews I conducted for a polo program opens up with a fill-in-the-blank question, Barbara Walters style:

“Polo is…” I asked, and the blonde polo player patron answered, “Polo is inclusion.”

Welcome to my world.


“I got along better with the guys than with the girls. Only two girls came up to talk to me.
Later, I found out they were telling their boyfriends, ‘If you talk to her, I’ll kill you.’
It’s always rough with that high school thing.”
— Christina Aguilera


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