This is the first in an ongoing series where Scott is going to arbitrarily match up famous drunk people and ruminate on who would win in a drink-off.

This month, it’s writers.

Ernest Hemingway vs. F. Scott Fitzgerald

From what I’ve read about their infamous feuds, Hemingway was endlessly dickish to colleague and sometimes-friend Fitzgerald—hating on him in public forums and constantly ragging on him for his inability to drink like a man. Fitzgerald was a better writer than Hemingway, whose prose is so terse and uncomplicated that he may as well have written in morse code, but Hemingway would probably win in a drink-off if his assertions about Fitzgerald’s inability to hold his liquor are true. In these kinds of competitions, it’s either the manlier or the crazier one who wins, and both of these dudes were crazy. Plus, Hemingway would be able to wake up and write with a hangover on account of his sentences being about as complicated as the ones I found in my Phonics book in second grade.

Raymond Chandler vs. Charles Bukowski

These two were both known as being heavy, heavy drinkers who were awful to be around pretty much all the time. One would think that Bukowski’s tenacity would bode well for him in a drink-off, but I think it might prove a detriment if he were to face off against Chandler. See, Chandler would use his stellar wit with a tight sarcastic bent to piss Bukowski off to a point that Buk physically assaults Chandler and is disqualified from the competition.

Dylan Thomas vs. John Berryman

This is a showdown of the poets, both of whom are rather legendary for their alcoholism. Thomas would win, because Thomas ultimately drank himself to death, and you can’t really beat that kind of person in a drink-off. If your life is a game of drinking, doing it ‘til you die is like winning by forfeit.

Mark Twain vs. Jack London

London is on the record as saying he never didn’t want a drink, which is the kind of quality you want in a person in a drinking competition. However, Twain spent most of his life messing with people in order to prove a point (much like Kurt Vonnegut). He would sometimes abstain from drinking and smoking (both of which he did from waking to sleeping) just to prove to people that he wasn’t a slave to his vices. If you reverse that premise and keep the same mentality, Twain isn’t going to be out-drunk by anybody, just out of principle.

William Faulkner vs. Tennessee Williams

I’ve got to give this to Faulkner, on account of his reputable ability to slam whiskey whenever he wasn’t working. A binge-drinker with discipline like that is going to be a great competitive boozer. Also, Williams died by choking on the bottle cap for his eye drops. Doesn’t seem like a guy you want in your corner, really.

Dorothy Parker vs. John Cheever

These two were both very sad individuals for much of their lives, but they were amazing writers and amazing drinkers. I give the nod to Parker, because her abrasive wit would drive Cheevs to quit in favor of a pouting session.

Edgar Allen Poe vs. Truman Capote

I won’t contest that while working on In Cold Blood, Capote saw and hear some stuff that might make a guy want to have a three-martini lunch. But Poe was completely out of his mind and totally dedicated to the sauce. I feel like Poe was kind of a pioneer of the “Getting Weird” aesthetic, and as such believe he would dominate Capote in head to head battle.

Hunter S. Thompson vs. Jack Kerouac

Like any dude who thinks it would be cool to have a job you can sometimes do while hammered drunk and on all kinds of experimental drugs, I grew up a huge Thompson fan. I watched the many documentaries made about him, and in doing so have drawn the conclusion that he might be able to out-drink anybody on this entire list. Toward the end of his life, the guy’s tolerance was beyond anything I could even comprehend.