Chairry is a bluish-green armchair with eyes on the chair back, a mouth between the seat cushions, and armrests that flapped around and occasionally hugged Pee-wee when he sat on her. She dislikes being jumped on, as evidenced in the episodes The Gang's All Here and Sick, Did Somebody Say Sick?.
Voiced by Alison Mork in Pee-Wee's Playhouse and Lori Alan in the 2010 revival of The Pee-Wee Herman Show.
Chairry is a light blue armchair with feminine eyes on the inside back and cushions for the mouth.
- Chairry's 2010 voice actress, Lori Alan, also voices Pearl in SpongeBob SquarePants.