A person that gives unwanted and unsolicited advice while he watches others play a game he is highly proficient at.
Coined by Egoraptor of Game Grumps when playing Super Smash Bros, warning his viewers that he was only playing for fun, and that savvy players should avoid microscopic critique of his play in the comments section. It happened anyway.
Player 1: (Makes a common mistake)
"Shoulda Rolled" Guy: "You should've rolled."
Player 1: "Shut the fuck up and let me play."
Egoraptor: "He had this whole essay of advice and even offered to train me."
JonTron: "Wait, seriously!?"
Egoraptor: "Ugh, I just KNEW there was gonna be one of those people, a fucking 'Shoulda Rolled' guy."
The day looked forward every year by many people across the earth. This is a signifigant day in history. August 31st marks the day that man first rolled his towel.
And since that historic day, man (And woman) has been rolling their towels.
A cinnamon roll, or, smol cinnamon roll/precious cinnamon roll/etc., is a cute, oblivious, innocent, sometimes helpless, character, that always has HORRIBLE stuff happen to them.
Jack Roller: in nineteenth and early Twentieth Century America a Jack Roller was a guy who hung around the skid row sections of big cities and robbed those unwise enough to get visibly drunk by beating them up and stealing their valuables. He "rolled drunks," and was called a Jack Roller. A Jack Roller's crime is also called, "Strong-arm robbery." Jack Roller is an old term still used on San Francisco's and Seattle's waterfront.
"He's a low-life," the bouncer said to the bartender in a waterfront saloon. "He's a jackroller. He beat up an old guy pretty bad last week, just to steal a couple of dollars from him."
In military parlance it means anything crappy coming from the top of the chain of command will hit everyone down to the bottom. This includes dumbass decision making, disciplinary actions, or simply a superior taking his frustrations out on subordinates.
Privates, I'm knee deep in your ass right now because the 1st Sgt was knee-deep in my ass this morning, and shit rolls down hill!