Date: Circa early 1998.
Medium: Pen & ink on paper.
"Uncle Bob" was a character developed by Eric Hooton and Bryan MacAfee around the 1994 timeframe. He was a shlub with a crew cut, swollen nose, moustache, potbelly, and a shirt that read "I <3 THIS." Though he wasn't my creation, I still did my fair share of Bob art with MacAfee, as with the previous Borg Bob.
If Bob were a dinosaur, this is how he would look. That's really all I can think of to say here.