RORY: I also pictured you with Pee-Wee Herman.
RORY: Yeah. We lived in his playhouse and we’d be talking to Chairry and Captain Carl would be walking by.
Pee-Wee Herman, fictional character portrayed by comedian Paul Reubens (born Paul Reubenfeld 1952). The child-like Pee-Wee Herman developed as a stage act and then appeared in a feature film before becoming the host of Pee-Wee’s Playhouse, an Emmy-winning children’s show that was broadcast from 1985 to 1991.
Chairry was a puppet armchair, voiced by Alison Mork, which would hug Pee-Wee when he sat down in her. Captain Carl was one of a host of human characters in the show; he was a sea captain played by Saturday Night Live comedian and actor, Phil Hartman (1948-1998). The show had a lot of big stars on it, and guest appearances by a host of celebrities.
Rory would have watched the show as a preschooler, apparently looking to the child-like Pee-Wee Herman for a possible father substitute.