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Wooly Willy

Drawing prompts

Fifty faces to draw on Willy

A structured prompt list, from two-minute mustaches to full portraits, because everyone runs out of ideas after the beard.

Why a list helps

Every session starts the same way: mustache, eyebrows, silence. The toy has no levels, so it needs prompts the way a blank page does. Read one out loud, argue about the result, tilt, repeat. The prompt spinner on this site deals these at random; the list below is the same idea on paper, sorted by effort.

Two-minute faces

  • A handlebar mustache and nothing else
  • One giant unibrow
  • A tiny goatee, way too small for his face
  • Sideburns down to the chin
  • A single curl on top, cartoon-baby style
  • Angry eyebrows
  • Surprised eyebrows, halfway up the forehead
  • A soul patch
  • Three hairs total, combed over
  • A milk mustache

Five-minute faces

  • A full pirate beard with a curled mustache
  • A mohawk
  • Muttonchops joined to a mustache, no chin beard
  • A wizard beard, longer than the chin allows
  • Slicked-back hair with a widow’s peak
  • A flat-top haircut
  • Cat whiskers and pointy ears
  • A monocle and a thin mustache
  • Winter mode: hat, earmuffs, chin scarf
  • A lion mane all the way around

Character studies

  • Your grandfather, as accurately as possible
  • A sea captain who has seen things
  • A 1970s rock drummer
  • A distinguished professor mid-lecture
  • Santa in the off-season
  • A detective in a deerstalker hat
  • A viking, horns optional
  • The barber gave up halfway
  • A judge with powdered wig
  • Every uncle at Thanksgiving, one at a time

Challenges and games

  • Draw with your eyes closed, then guess what it is
  • One player draws the left half, the other the right
  • Copy the face of someone in the room until they notice
  • Give Willy the hair you had in your last school photo
  • Speed round: best mustache in twenty seconds
  • Draw the same face twice in a row, exactly
  • Pass the wand every ten seconds, no talking
  • Make him sad, then fix it with one drag of the wand
  • The dictionary game: someone names a word, draw it as hair
  • Draw the most hair the board can physically hold

The long game

  • A four-season series: same face in spring, summer, fall, winter
  • His entire life story in five faces, bald to bald
  • A family portrait: draw each member of your family in turn
  • Recreate a famous painting, argue about which one it was
  • Draw yesterday’s weather as a hairstyle
  • The before and after of a barbershop visit
  • A face using only taps, no drags
  • A face using only one continuous drag
  • The world’s worst haircut, then vote
  • Freestyle: empty the whole bottom pile onto his head and sculpt down