Massey - All the lives I want: essays about my best friends who happen to be famous strangers

We realized that the version of the world they rendered for us was not the world they really believed in.

Jeffrey Eugenides, The Virgin Suicides

I SHOULD HAVE FORESEEN THAT things between James and me would end in violent chaos on the night of my twenty-ninth birthday when he, my best friend Phoebe, and I were each contemplating who our No. 1 most bangable celebrity was. Phoebe and I had declared our respective loves for Harry Styles and John Malkovich. Then James said, You know, Ive always had a soft spot for Gwyneth Paltrow.

Gwyneth Paltrow? I repeated back to him in horror.

Yeah, theres something about her. I dont know what it is! And in that moment, every thought or daydream Id ever had about our potential future together filled with broad-smiled children, adopted cats, and phenomenal sex evaporated. Because there is no future with a Gwyneth man when youre a Winona woman, particularly a Winona in a world made for Gwyneths.

Just as Phoebe and I wax poetic about which celebrities wed let impregnate us, weve also devoted considerable time to the ones we feel our lives most resemble. It is from this game that I developed my Winona in a world made for Gwyneths complex. This theory positions these onetime best friends as two distinct categories of white women who are conventionally attractive but whose public images exemplify dramatically different lifestyles and worldviews. The interesting thing Ive found about asking women whether theyre Gwyneths or Winonas is that self-assessments are almost universally in concert with external assessments. Ive seen dramatic escalations when a self-identified Charlotte was told by friends that she was a Miranda, but for the most part, Winonas know that theyre Winonas and Gwyneths know that theyre Gwyneths. Whats more interesting is that people are usually happy about it, too.

One lives a messy but somehow more authentic life that is at once exciting and a little bit sad. The other appears to have a life so sufficiently figured out as to be both enviable and mundane. Gwyneth Paltrow is, of course, the latter. She has always represented a collection of tasteful but safe consumer reflexes more than shes reflected much of a real personality. I imagine that she writes the GOOP newsletter, her laughably out-of-touch dispatch about vegetables and fashion, wearing overpriced clothes in colors like camel and scowling at

For girls of my generation who were awkward or a little bit strange, Winona Ryder was both relatable and aspirational. The few recorded interviews shes done reveal that she is a bottomless well of uncool and discomfort. She stumbles over metaphors and laughs sincerely at bad jokes. She is also a movie star who is unreasonably beautiful, but there was always a sense that she still belonged to the Island of Misfit Toys.

She epitomized the Mall Goth ethic and aesthetic in Beetlejuice long before Hot Topic was mass-producing the look, and in Heathers, she enacted high school revenge fantasies long before Mean Girls was either a movie or PG shorthand for fucking bitches. In the 90s, she did her grungiest best as the Generation X poster child in Reality Bites but never met a corset she didnt like and came at us with The Age of Innocence and Dracula. I cant even talk about Little Women, because Ill just start crying about the fact that Im not currently sitting under a pile of kittens and sisters.

Then theres her romantic life, which reads like a whos who of my sexual awakening. Val Kilmer, Rob Lowe, Christian Slater, Beck, David Duchovny, and a bunch of indie rock stars who are probably still in love with her. Gwyneth had a shorter and more predictable list of conventional handsome dudes, including Brad Pitt and Ben Affleck, before she married Chris Martin. But Winonas love stories seem like a series of elaborate fan fictions come to life for the charming and constantly bewildered pixie of a person. And Im sure I dont need to remind anyone that Johnny Depp wore her name on his bicep when he was still starring in daring, quirky films instead of predictable Tim Burton cash cows.

But just as Winonas legendary series of whirlwind romances wouldnt last forever, neither would mine with James. Many of the tabloid stories reported that she was devastated by her relationships ending. I realize that celebrity breakup synopses often cast the woman as the sad sack who cant catch a man with a net because its a neat narrative. But, good god, it was also my narrative and I needed a hero.

As interesting as I always found her love life, though, it was still her personality and talent that drew me in. Rumor has it that Winona had the script for Shakespeare in Love and that Gwyneth saw it at her house and surreptitiously sought out the producers to get the role that landed her the Oscar. It is one of many Hollywood whispers that Gwyneth is not so sweet as she presents. And the long list of best friends she seems to have had over the years (Winona, Madonna, Tracy Anderson, Beyonc) looks more than a little opportunistic.

It would have all been fine for Winona, because she was starring in the adaptation of