Peewee is a size joke that's been a staple of American pet naming for at least a century. It's almost always given to small dogs, carries an inherently affectionate diminutive quality, and has a certain old-school charm that makes it feel like something your grandfather's dog might have been called.
The Small Dog Name Tradition
Peewee sits in a cluster of size-coded pet names (Tiny, Peanut, Micro) that all work by the same logic: naming the dog's most notable physical characteristic and committing to it. Chihuahuas and Yorkshire Terriers collect these names in disproportionate numbers.
Pee-wee Herman and the Pop Culture Layer
Pee-wee Herman, Paul Reubens' beloved character from Pee-wee's Big Adventure (1985) and the Saturday morning show, gave the name a specific comedic register in American culture. Some dog owners in their 40s-50s are almost certainly pulling on that nostalgia. It maps well onto small, high-energy dogs with enormous personalities.
Why the Male Skew
The male preference at rank 2269 is consistent with most size-diminutive pet names — Tiny and Peanut also skew male. The implied toughness-versus-reality gap works differently on male dogs, apparently. Forty-two registrations is exactly what a name this specific deserves.