Clippy

"You look like you're trying to eat me. Need some help?"

- Clippy

"Looks like you're trying to blow up the computer. Mind if I hug my kids?"

- Clippy

Clippy, real name Clippit, is the assistant.

History
When Strangles was trying to eat a computer, Clippy appeared on the screen and said "You look like you're trying to eat me. Need some help?".

When Sideshow Bob attempted to kill the Simpson family with a defective laptop and a pile of dynamite, Clippy appeared on the screen of the laptop and said "Looks like you're trying to blow up the computer. Mind if I hug my kids?".

When Homer was hiding from a guy with a gun, he hit himself on the head to get his illusion of Stradivarius Cain back. When Clippy came up, Homer said that he was a big fan.

Non-canon
Whilst investigating information leaks on computers, Chief Wiggum mentions that his informant on the inside, Clippy, has given him useful tips on how to format letters.

Behind the Laughter
Clippy is the common nickname for Clippit, the for Microsoft Office from  to.