The Announcer

From Homestar Runner Wiki

This guy appears in "Marshmallows Last Stand" and "A Jumping Jack Contest," although his voice is heard in several subsequent cartoons (e.g. SBEmails "Mascot" and "Suntan"). He looks kind of like Coach Z with a monocle and a big moustache.

The Barbershop Trio who sings the Ballad of the Sneak, voiced by real-life band DaVinci's Notebook, are all lookalikes of The Announcer, and probably his 1936 versions.

He can also heard in "The Reddest Radish" announcing that they should all bring their radishes to the staging area and as the narrator in "The Search for the Yello Dello".