This meme would probably hit a lot harder if I had any idea who even a single one of these men were. Throwing niche memes in the big meme basket is a bold strategy
They are all characters from the show Suits. I used to be subjected to it by my girlfriend. The whole show is corporate fetishism. It's like House, but with lawyers. The average episode revolves around characters finding clever ways to fuck over old acquaintances, usually in the course of representing their incredibly shitty clients. Every single characters is an unlikeable arsehole who works from 5am in the morning to 2am the next day and spends the remaining 3 hours of free time drinking whisky in their office and brow-beating their colleagues who are also still in the office in the middle of the night.
Guy on top left is suave boss man lawyer. He drinks the most whisky. Guy on top right is his plucky upstart protégé lawyer. He drinks the least whisky. Guy at the bottom is the comic relief lawyer. I can't remember if he drinks whisky.
I was late to the SUITS party and thought this -- but in a moment of WCGW, someone who didn't know I'm only in season 4 dropped a big spoiler. Don't read all the comments but do watch Suits -- it's fun.