The phrase, as well as the image originate from the 2003 racing disaster, titled Big Rigs: Over the Road Racing.
The game itself is notorious for its large number of bugs and errors, that make it almost unplayable.
Upon the release of the game on November 20th, 2003, the smallest error in players could find was the grammatically incorrect “You’re winner” message at the end of every premature victory, due to the AI’s lack of intelligence – and other bugs.
Unsurprisingly, the game received a lowly reception, becoming a laughing stock for everyone before forgetting about it.
“You’re winner” was first defined on Urban Dictionary in March 2004.
Toward the end of the 2000’s, the game started developing a slight meme presence on the internet, as YouTubers would upload reviews of the game.
One notable example is Angry Video Game Nerd’s review of the game, uploaded to YouTube by Cinemassacre on March 19th, 2014.