Man, I'm glad I found this thread.
Ponyfied Homestar Runner
Type: Earth pony
Coat color: Red with white head and hind legs (nonexistent front legs)
Mane color and style: Something resembling Homestar's propeller cap
Eye color: Black "comma" eyes both visible
Cutie mark: A solid white 5-pointed star
Pose: Side view, with H*R style head profile. Standing on "all" fours, but "holding" a slice of pie, about to eat it, or a glass of piemonade with a straw about to take a sip
Expressions: the open mouth of the HRwiki main page
Accessories or costumes: if the propeller cap doesn't work as a mane, just stick a normal one on top of the head. Also, the large shoes would be nice, but I'm not sure how good that would look on a pony.
If anypony takes on this request, please PM me about it. Also PM if you need any clarification. If you don't understand the character I want, check out the HRwiki article on Homestar Runner. Thank you.
E: By the way, if you think it would look better in a different pose, let me know. We know from "Suited for Success" that the customer is not always right.