Jack Dorseys, Ranked

Jack Dorseys, Ranked
Photo: Joe Raedle, Getty Images

If you try to picture the CEO of a given tech company year by year, there are usually a few distinctive features that stay pretty static. Mark Zuckerberg’s aggressive hairline has kept on being aggressive, Jeff Bezos has kept on being bald, and Elon Musk has kept on being a moleman.

There is one obvious exception to this rule though: Twitter CEO Jack Dorsey. The man’s gone through multiple personas over the years, most recently channeling an extra from That 70’s Show when he made an appearance at a massive crypto conference in Miami last week. In honour of the platform’s (incredibly tan) overlord, I decided to hit up some of Jack’s greatest looks through the ages, and to try — for what has to be the first time ever — to definitively rank every Dorsey.

Jack “Ladies Drink Free” Dorsey

Photo: Francois Durand, Getty Images Photo: Francois Durand, Getty Images

First up is a man who’s either New York’s most off-putting club promoter or at the very least will definitely end up causing Fyre Festival part 2. Either way, avoid! at! all! costs!!! -5/10

Jack “Check Out My Nine Inch Nails Cover Band” Dorsey

Photo: Dominique Faget, Getty Images Photo: Dominique Faget, Getty Images

After letting his platform fester for…. more than a decade, our newly shaggy boy finally took a few baby steps towards making his platform a bit less 0f a hellscape in 2019. And I do mean baby steps: banning political ads that nobody was running in the first place and revamping (a few) of the platform’s arcane policies surrounding hate speech. But at the same time, he keeps on handling the near-daily political uproar unfolding on his site with kid gloves, even doubling down when asked to maybe, just maybe, boot certain noted white supremacists off the platform. The haircut’s pretty dope though. 1/10

Jack “Oopsie Woopsie” Dorsey

Photo: Phillip Faraone, Getty Images Photo: Phillip Faraone, Getty Images

On one hand, 2018 was the year when Dorsey finally acknowledged to lawmakers and the rest of us that yes, his platform does have a massive misinformation problem, issues with violent harassment, and swarms of bots. He’d ask questions during interviews — like the one pictured at the WIRED Summit here — about the sort of “incentives” baked into the platform’s design, and whether a company’s “rules” should override its “values” or vice versa.

Less clear was what the hell he actually planned to do about the aforementioned misinfo, harassment, and bot problems. For the most part, Dorsey spent most of his time with reporters doing his best impression of a very apologetic (and vaguely sweaty) brick wall. 2/10

Jack “This Edible Ain’t Shit” Dorsey

Photo: Kara Andrade/, Getty Images Photo: Kara Andrade/, Getty Images

It was the spring of 2007. Akon and Fergie were at the top of the charts, nobody could stop talking about Zach Snyder’s 300, and the word was starting to get around about this weird new microblogging startup called… Twitter. CEO Jack Dorsey and co-founder Biz Stone described the site as something like a cross between traditional texting and long-form LiveJournal-ing. The New York Times ran a column questioning whether the “radical self-revelation” this setup invited was even healthy for people to engage with (spoiler: it’s probably not!). But we’re not here to talk about any of that. Instead, I just want you to take a good, long look at Dorsey’s face in that picture.

Is he smiling? Can you call that smiling? Are his eyes actually looking at anything in the room? Do you think he knows where he is right now? Do you think he had a sudden premonition about the cesspit his startup would one day become, and he’s just sitting there, screaming internally?

Either way, it’s a pretty mediocre start. 3/10.

Jack “Space Monkey” Dorsey

Photo: Andrew Burton, Getty Images Photo: Andrew Burton, Getty Images

Our shiny CEO shows some(?) sort of human emotion. This was taken in 2013, on the trading floor the night Twitter had its stock market debut. The platform was enough of a cultural phenomenon at this point that the IPO turned into a media event, too — this was the first time that the New York Stock Exchange ever livestreamed a company’s IPO. And what better way to commemorate this massive career milestone than paying homage to the buzz cut Brad Pitt was rocking towards the end of Fight Club.

Before you fire off an angry comment about how that shaved scalp “definitely isn’t an homage to anything” and that “dude was probably just being comfortable under all those fluorescent lights” — I know. Let me have this. 5/10.

Jack “Torrence” Dorsey

Photo: Jemal Countess, Getty Images Photo: Jemal Countess, Getty Images

There’s something really disturbing about this particular Dorsey, which features our guy being honoured at the 2012 Tribeca Film Festival alongside a pre-tattooed Justin Bieber and his manager, a less scandal-ridden Scooter Braun. In the five years since that first photo was taken, Jack’s dead-eyed leer hasn’t necessarily gotten any less creepy — the blazer-hammer combo really pounds that point home. In fact, I’m almost positive that Jack Nicholson’s character made this exact face in The Shining right before trying to go bludgeon his wife and son to death. Now that I think about it, who the hell gave him that hammer anyway? Have we ever heard from them again? 6/10.

Jack “Burnout” Dorsey

Photo: Justin Tallis, Getty Images Photo: Justin Tallis, Getty Images

The Dorsey we started getting in 2014 is one that feels like a weirdly prescient portrayal of pandemic-induced exhaustion: someone who’s kinda scruffy, often in a sweatshirt, and visibly teetering on the edge of an emotional breakdown. Is Jack doing his Classic Not Smile here, or is he literally about to cry? It’s honestly a toss-up. This picture was snapped at an event where Dorsey was set to announce a new mobile app to accompany his new payment biz, Square, which burned through nearly $US100 ($128) million the year prior while publicly struggling to keep itself afloat. A month after this picture was taken, Square announced that it would be severing its relationship with Starbucks after it lost a good $US71 ($91) million processing payments for the coffee chain. Sorry, buddy. hug/10.

Jack “Procedural Cable Drama” Dorsey

Photo: Drew Angerer, Getty Images Photo: Drew Angerer, Getty Images

The overwhelming Law & Order: SVU energy oozing from this 2016 photo (featuring venture capitalist Aviv Nivo on the right and McDonald’s CEO Steve Easterbrook on the left) is impossible to put into words. Instead, I’d recommend playing this opening theme song and picturing a dead body somewhere offscreen. Don’t worry about how the body got there. 9/10

Jack “The Beard” Dorsey

Photo: Greg Nash-Pool, Getty Images Photo: Greg Nash-Pool, Getty Images

When Dorsey called into the Senate GOP’s hearing on… “online platforms censoring conservative speech” at the end of last October, there was a brief second where everyone got to ignore the political circus happening on the floor to gawk at whatever was happening on the Twitter CEO’s face. Dorsey had rocked a beard in the past, but this shaggy/whispy hybrid had taken on a life of its own. Reporters dared to ask what secrets he was hiding in there. Others pointed out that the beard, not Jack, should be on that stand. It made a cameo on SNL. In its short tenure living on the bottom of Jack’s face, it’s more popular and seemingly more well-liked than Dorsey himself. I mean, just look at it.

Jack: 3/10

Beard: 9.5/10

Jack “Jimmy Buffet Is A Visionary” Dorsey

Photo: Joe Raedle, Getty Images Photo: Joe Raedle, Getty Images

Yes, Dorsey made a cameo at the Crypto convention that happened in Miami last weekend. Yes, the same one that let people walk around mask-free and didn’t ask anyone for proof of vaccination, only for attendants to later report that they (shockingly!) caught COVID-19. Honestly, I’m not sure whether to be more appalled at Dorsey’s flagrant disregard for public health here, or the fact that he’s now become indistinguishable from the generic weed guy you undoubtedly knew in college. 10/10