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
Boards this guide keeps mentioning
The one in stores


Original Wooly Willy
The current PlayMonster box of the 1955 magnetic drawing toy, and the listing most people land on first.
$7.994.4 stars, 5,097 voices
Travel and gift pitch
Wooly Willy: travel and gift listing
The newest listing on the shelf, pitched at road trips, party bags and the bottom of a stocking.
$4.994.2 stars, 30 voices
