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"~uguu" is a line uttered a large amount by the character Ayu Tsukimiya originally in the Japanese Erotic Romance game "Kanon", released in 1999 for the Windows PC, also released for the Playstation, Playstation 2 and Playstation Portable. "Uguu" has gained a large bit of fame in the weeaboo community, and is used frequently.
Kanon was originally an adult visual romance novel released in 1999, following the exploits of a man named Yuichi Aizawa as he struggles with a form of amnesia. By meeting several woman, he slowly regains his memory. Since it's release, Kanon has sold over 300,000 units worldwide.
An anime by the same name was released in 2006 by Kyoto Animation, which gained significant popularity due to its tie in with the web novel.
Beginning as a term
Uguu was originally said in the anime by the same name as the novel released in 2006, however it is unknown when it began to gain fame on the internet. Uguu is a term to describe moaning or whining (from urban dictionary, "like eeeehh, but more original.") Uguu has gained popularity in the Japanese community since.
Related Character: Tsukimiya Ayu
In the anime and the novel, Ayu Tsukimiya is one of the love interests for Yuichi Aizawa. She is defined by high voice and extreme shyness in general. Tsukimiya is the main heroine of Kanon, and therefore is very popular. Tsukimiya has received merchandise and other adaptations, such as fanart, including backpacks and lunchboxes.
Related Term: "Am I Kawaii? Uguu…"
"Am I Kawaii? Uguu…" comes originally from a character in the "What's with all the racket up here, son?" meme comic, after the man's father walks in on him watching anime. The character on the screen asks "am I kawaii, uguu…", followed by a face of disgust from the man's father. This term has gained popularity for it's poking fun at weeaboos.