Here's my theory on Bosco's mother-dressing. Many, many moons ago, there was a bright young man named Stephen Purcell. The world was his oyster, and he couldn't have been happier. One fine day, Steve said to the local barkeep, Mabel,
"Say, I have an idea. People like to laugh, right? Well, how about a comic about two 'freelance police' named Sam & Max? Sam could be a lovable dog whose personality harkens back to the time of Bogart, and Max could be a rabbit with a severe mental disorder!"
Steve rushed home that night, sketchbook in hand, and began drawing at a feverish pace. The rest was history.
Cut to 2007, at the Telltale Headquarters/Steakhouse. A bright young man named David Grossman sat at his desk, wondering how to capture the vision of Steve Purcell for the 6th time. He scanned the Telltale forums for inspiration, since a delightful ragamuffin named ShaggE often posted there, and everyone at Telltale was always talking about how they should hire him to write Season 2.
Unfortunately, ShaggE was away that week, so Dave had to come up with something funny on his own. He asked himself, "What would ShaggE do?".
He thought, and thought some more. "EUREKA!" Dave exclaimed. "I'll have Bosco crossdress! Nobody will expect it!"
And so, a joke was born. This concludes our story on why the dude looks like a lady. Visit your local library for more info.