It’s nearly impossible to be cool. Trying to be cool is the lamest thing imaginable, but also, merely Not Caring isn’t nearly enough. I don’t mean baseline cool, the way people think, like, Phoebe Waller-Bridge is cool. Or “does drugs and says whatever they want” cool like Lou Reed. I mean forever cool.
You have to be comfortable in your own skin without projecting too much confidence (Vin Diesel). You have to make/do something cool without working too hard, or selling out (Bruce Springsteen doing a podcast with Obama…uncool!). You have to be, at your core, a good person. But if your thing is making the world a better place, you end up on the path to Great, which is not the path that leads to Cool (Abraham Lincoln, Paul Newman). You can’t be a ham (Elaine Stritch), nor take yourself completely seriously (Daniel Day-Lewis). You have to have a bit of edge (sorry, Meryl, Denzel, Paul Simon, George Harrison), but not so much you become obnoxious (Morrissey). Emma Stone is too sweet; Bill Murray too sour.
What’s especially paradoxical is that when people look for examples of cool, we use celebrities, but fame is uncool. Mystery is cool. Honestly, fame is cringe. The world got too obsessed with Elvis; Mick Jagger is too obsessed with Mick Jagger. Keke Palmer was so clearly born to be famous…she’s a star! But not cool. And if the fame becomes part of your brand, it can undo your cool. See: Jack Nicholson, Spike Lee, anyone who loves sitting court-side. You also can’t be cool if you’ve ever had your own show (Cher) or done a “Masterclass” series (Steve Nicks).
Steve McQueen so thoroughly defined cool that he became a cliché and…fell out of coolness. I fear the same fate may soon befall Harrison Ford. The Cut once declared Haim corny, then six years later admitted the band rocks. It’s hard.
With all that in mind, I have identified 5 cool dead people, and 10 probably cool alive people (since being alive is inherently disgusting, no living people can safely say they are cool, plus, there’s still time for them to suck before they die) (On the other hand, you have to live long enough, or else there’s no way to know how much of your cool factor is your early demise, i.e. James Dean, Selena Quintanilla)
The Only Cool People Ever
Johnny Cash
Self-explanatory.
Tina Turner
Maybe our last cool pop/rock star. Her journey was incredible, but I am skeptical of what might have come of it if she’d been posting on social media along the way.
Carrie Fisher
Self-explanatory.
Bruce Lee
Self-explanatory.
Lenny Bruce
Stand-up comedian is one of the least cool professions. Only Lenny pulled it off.
People Who Are On Track To Die Cool
Keanu Reeves
Leading contender for coolest man, but we’ll see what his post-John Wick career looks like. Hoping he doesn’t start a vodka brand or write a book of bad poetry.
Sofia Coppola OR Paul Thomas Anderson
Both of these people have cool lifestyles and personalities and their movies are 10/10 on performances, humor, style and vibes. And yes, they elicit emotional reactions. But do they take real risks? Do they SAY anything? They explore, but do they stake claims, make waves? The first to stir up a proper controversy wins.
Rihanna
Clearly our coolest woman, but, I fear, on the verge of selling out / over-exposure. I’m sorry! It’s not about the lack of a new album, the album will come when it comes. It’s the many brands. She’s one brand away from too many brands.
Fiona Apple
All the makings of a cool person, but unapproachable. Needs to be a meme or something. Humanize her two percent.
Tony Hawk
Enormous dad vibes counteracted by the fact that he’s a skateboarder. Also, hot.
Dave Grohl
Enormous dad vibes counteracted by the fact that he’s a rockstar. Also, hot.
Lucy Liu
Hard worker, boundary-breaker, server of face, deadpan humor…all the makings of an icon, but the cool factor? Her lesbian art.
Chloë Sevigny
The only It Girl who matters and it’s honestly embarrassing watching NYC nepo babies try to do what she did.
Solange
Possibly too polished and child star-y to speak to her moment, but when she went off on Jay-Z in that elevator I saw a flicker of cool, so you never know!
Also, Jesus, the real guy not the religious figure depicted by conservatives...pretty cool!
Things I got free from Brands this week:
a galley of Caroline Calloway’s book Scammer. It’s delicious. She’s not cool but she’s a hot mess, which is just as good of a temperature.
Coldly,
Lizzie
Extra points for Dave Grohl--was a star drummer before switching to guitar.
First of all, another example of how I don't need a newsletter because Lizzie is writing my thoughts down for me. On the living list, Lucy Lui is the coolest for exactly the reason given. A personal art habit (especially in a medium that is accessible but somewhat expensive and time consuming, just the sort of thing any cool person might dabble in if given the time/financing) is essential - Ms. Lui is enriching herself for the love of the game! Accurate reading of SC and PTA but I give Sofia the edge because she risks nothing and that's the point? She embodies an untouchable-by-criticism quality that younger nepo babies have lost. Also because every photo of a room she occupies is a goddamn ephemera goldmine.