All the Lives I Want: Essays about My Best Friends Who Happen to Be Famous Strangers

All the Lives I Want: Essays about My Best Friends Who Happen to Be Famous Strangers

Alana Massey




For my sister Nova, the first star I ever wanted to be.





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





Being Winona; Freeing Gwyneth


On the Limitations of Our Celebrity “Type”


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, I’ve always had a soft spot for Gwyneth Paltrow.”

“Gwyneth Paltrow?” I repeated back to him in horror.

“Yeah, there’s something about her. I don’t know what it is!” And in that moment, every thought or daydream I’d 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 you’re a Winona woman, particularly a Winona in a world made for Gwyneths.

Just as Phoebe and I wax poetic about which celebrities we’d let impregnate us, we’ve 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 I’ve found about asking women whether they’re Gwyneths or Winonas is that self-assessments are almost universally in concert with external assessments. I’ve 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 they’re Winonas and Gwyneths know that they’re Gwyneths. What’s 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 she’s 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 her staff. That is, when she’s not referring to Billy Joel as “William”1 and seeking nannies who know ancient Greek and play at least two instruments.2

For girls of my generation who were awkward or a little bit strange, Winona Ryder was both relatable and aspirational. The few recorded interviews she’s done reveal that she is a bottomless well of uncool and discomfort.3 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 didn’t like and came at us with The Age of Innocence and Dracula. I can’t even talk about Little Women, because I’ll just start crying about the fact that I’m not currently sitting under a pile of kittens and sisters.

Then there’s her romantic life, which reads like a who’s 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 Winona’s love stories seem like a series of elaborate fan fictions come to life for the charming and constantly bewildered pixie of a person. And I’m sure I don’t 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 Winona’s legendary series of whirlwind romances wouldn’t 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 can’t catch a man with a net because it’s 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.4 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, Beyoncé) looks more than a little opportunistic.

It would have all been fine for Winona, because she was starring in the adaptation of Girl, Interrupted. Except that turned out to be the movie that would actually work to catapult Angelina Jolie to stardom and earn her an Oscar. And then came her 2001 arrest for shoplifting. The incident revealed a more complicated, less whimsical Winona; she was actually unwell, an inconvenient reality better dealt with through punch lines than public sympathy. And while male performers have gone on violent and destructive benders and bounced back in the time since that incident, Winona’s reputation has never fully recovered.