"I don't think so ... Homey don't play that!"

Herman Simpson, better known semi-professionally as Homey D. Clown, is a bitter and hostile convict with a never-ending community service sentence. The anti-social Homey is often seen entertaining a group of excited children, who all remain his biggest fans even though he degrades them and thumps them on the head using a sock with a tennis ball inside.


Homey has a questionable criminal history which has caused severe emotional problems, specifically a lifelong grudge towards The Man. This side of him comes out whenever he leads the children in a sing-along.

Much of the credit for the character goes to Paul Mooney, who was known to react "Aw no, homey!" whenever a writer pitched a sketch idea that might sound too racist. Damon became inspired, wondering "What if Paul were a clown?" -- and the rest is history.

Appearances (list in progress)Edit

Picture Title/Episode Description Cast
Birthday Party
Episode 109
At a birthday party, Homey does a trick with a dollar bill, and shows a clown-toon picture sequence of himself at Chez Whitey getting harassed by The Man.
Girl (Crystal): Why'd you become a clown then?
Homey: I guess it's because I got so much love to give. And it's part of my prison work release program.
  • Mother - Kim Coles
  • Kids - Kelly, David, Tommy, Crystal
Homey's One-Stop Carnival
Episode 113
Homey refuses to be dunked in water, but he will still make balloon animals (and pop them), spin you around in the Homey Whirl-Twirl, and put on a puppet show.
  • Kid 1 - David
  • Kid 2 - Crystal
  • Dad - extra
  • Cowboy - Jim
  • Cowboy's wife - extra
  • Whirl-Twirl guy - extra
When Homey Met Sally
Episode 202, Episode 226
Homey has a relationship with his parole officer. Can she change him? "I don't think so!" He uses eggs, milk and flour to show the kids what love is.
  • Stockbroker - extra
  • Sally - Crystal
  • Carnival barker - extra
  • Kids - Tommy, Kelly, David
Homey Claus
Episode 212
Homey fills in for Santa at the mall, giving the kids a different kind of Christmas cheer.
Kid (David): HI, HOMEY!
Homey: [Damon ad-libs] You scream in my ear again, big kid, it's gon' be me and you.
  • Kids - Jim, Kelly, Tommy, David
Home E. Cheese
Episode 214
At a birthday party, Homey converts a group of Woodpecker Scouts to an army of "Homey Whiz Kids" who revolt against their scoutmaster.
  • Kids - Kelly, David, Tommy, Crystal
  • Scoutmaster - Jim


Homey the Sellout - Part 1
Episode 224
It all starts at the Summer Arts Festival Day in the park. Homey is doing a drawing of some kids, when two spokesmen for The Man approach him and offer him a multi-million dollar endorsement deal. Homey signs, begins starring in commercials for Homey-Wheats Cereal, and soon becomes a rich celebrity.
Homey: So remember, little childrens, do what The Man says: go out and buy yourself a box of new Homey-Wheats, the only cereal made from cookies, marshmallows, sugar cubes, and other nutritional pieces of candy. Now this is a cereal Homey can play!

One night at Chez Whitey, Homey is about to enter and hobnob with his new snob friends, when his biggest fan tries to bring Homey to his senses. Has Homey lost his way?

To be continued …

  • Mime - Jim?
  • Juggler - extra
  • Kids - Crystal, David, Tommy
  • Executives - extras
  • Kids in commercial - extras
  • Julio, valet - extra
  • Homey's biggest fan - Tommy
Homey the Sellout - Part 2
Episode 301
At Chez Whitey, Homey finally sells out and gets to meet The Man … just so he can bop his big white head.
  • Kids - David, Tommy, Kelly, Crystal
  • Chez Whitey guests - extras
  • The Man - ?