Smeargle - duh
Trevenant or Sudowoodo - a happy little tree. One is a tree, one is significantly cheerier.
Pachirisu - Ross commonly rescued squirrels and sometimes had pocket buddies on the show
Bouffalant - his iconic hair style
Braviary - Ross was in the American military and spent time in Alaska
Lost on a sixth but I'm thinking something dark and kinda fucky. "Gotta have light and dark, dark and light in painting. Like in life."
