From Homestar Runner Wiki
The Announcer's name tells all, as he serves as an announcer or host wherever one is needed. He doesn't really let his personality show through, so little is known of him as a character, except that he does seem to be eager to do his job. He first appeared in the children's book, and hasn't changed very much since then. While he rarely makes actual on-screen appearances, his voice, which is earnest and mostly British, is used quite often. He resembles the members of The Barbershop Trio.
 Character Evolution
|This is the first design.||1996||Original Book; Strumstar Hammer (kids' book Easter egg); Strongest Man in the World||N/A|
|This is the second design.||1999||Marshmallow's Last Stand; lady...ing||He has thicker outlines and darker skin color. His mustache now curls up more. The colors on his clothes switch areas. The color of his neck is the same color as his face. His tie is gone and the shirt inside the suit is purple instead of white. His monocle is now blue and has a white reflection. His hands are now circles instead of ovals, and they appear to be smaller. He now has some shading.|
|This is the third design.||2000||A Jumping Jack Contest||His outlines are thicker and smoother, his skin is less pink and his monocle has more cartoonish shading. The shine on his monocle is more sharp, and has more shine than the last design.|
|This is the current design.||2006||Strongest Man in the World; yes, wrestling; Kick-a-Ball; hremail3184; On Break||His outlines are colored instead of just black, his mustache is more curved on the ends, he has a little glare in his eye, his colors are brighter and his tie is back. His monocle color is duller, and so is the luster of the shine. His hands now have shading and his arms and shirt have more, but his neck has less.|