Sara Gilbert Used to Be a Member of the P*ssy Posse

By Dustin Rowles | Celebrity | April 2, 2018 |

By Dustin Rowles | Celebrity | April 2, 2018 |

A couple of hours ago, while searching for an image to use for this Sara Gilbert post, I ran across this picture:

“Whoa!” I thought. That’s Sara Gilbert and Baby Leo. Huh. I wondered to myself if they were dating back in the day, and then I stumbled across this photo:

That’s Gilbert and Tobey Maguire! Maguire and DiCaprio, of course, were the leaders of the infamous P*ssy Posse, a group of successful and aspiring young actors who hung out and created mayhem.

I wondered: Was Gilbert in the P*ssy Posse, and a little sleuthing revealed that, indeed, she was:

From The Daily Beast:

Before we had Entourage, we had The Pussy Posse: Lukas Haas, Tobey Maguire, Harmony Korine, David Blaine, Jay Ferguson, Josh Miller, Ethan Suplee, Kevin Connolly, Scott Bloom, Justin Herwick, and occasionally Sara Gilbert.

From Complex, with a not-so-flattering, not-so-cool description:

But could something this male-centric, this exclusively XY (actress Sara Gilbert has been called an “adjunct member,” but she strikes me as someone the Posse has deemed cool enough and homely enough, and, you know, gay enough, for them to hang out with Platonically) not have an underbelly?

Finally, from NYMag, with a more flattering and accurate description:

An adjunct member of the pack is the heavy-haired Sara Gilbert of Roseanne, who was starring in Poison Ivy when Leo was just “Guy #1” in the script. “If they’re a new Rat Pack, she’s the Shirley MacLaine figure,” says a young actor who’s hung out with the crowd in L.A.

Here she is with fellow Posse members Kevin Connelly and Tobey Maguire, plus Soleil Moon Frye (aka Punky Brewster):

#tbt A long time ago in a galaxy far far away….. See any familiar faces?

A post shared by Kevin Connolly (@mrkevinconnolly) on Mar 19, 2015 at 7:56am PDT

Here she is way back when with posse member Jay Ferguson, who most of you better know as Stan Rizzo from Mad Men:

Interestingly enough, however, they have remained friends and continue to hang out. To wit: Here’s Gilbert with Kevin Connelly and Tobey Maguire’s wife.

The ’90s were a weird time.