|First Appearance||"22 Short Films About Springfield"|
|Voiced By||Hank Azaria|
Ian, The Very Tall Man is a man who goes around teaching bullies a lesson because he got bullied from second grade to high school. An extremely tall man who drives a Volkswagen Beetle and teaches bullies lessons, once Nelson was playing pranks it caught the attention of Ian, who proceeded to get out of his car and make Nelson take off his pants, so everyone could laugh at him. Ian made Nelson walk through the streets as he drove behind him. Ian was also seen on a bus to New York. He shops at Royal Majesty for the Obese or Gangly Gentleman.
- He is a caricature of writer Ian Maxtone-Graham, who is 6'8. They also share their first name.
- Episode – "22 Short Films About Springfield"
- Episode – "The City of New York vs. Homer Simpson"
- Episode – "A Midsummer's Nice Dream"
- THOH – "Treehouse of Horror VIII"
- Episode – "Ned 'N Edna's Blend"
- Book – The Simpsons Guide to Springfield
- Episode – "Summer of 4ft 2"