Pippin, Sam, Frodo, Merry
Just started rereading Fellowship of the Ring, and I love chapters 3-5 (Three is Company, A Shortcut to Mushrooms, A Conspiracy Unmasked). The four hobbits are so enjoyable to read that I was inspired to draw them, and in a manner that'd be fun for me to imagine as I continued progressing through the book. I'm especially happy with Merry, my favorite character, who I always imagined looking very jolly.
To fill you in on this illustration: to disguise his leaving the Shire, Frodo sells Bag End to the Sackville-Baggins and tells everyone he's moving to Crickhollow (in Buckland, where Merry lives). Merry arranges carriages to move his things, while Sam and Pippin accompany him on the trek by foot. A few days later they meet Merry on the road on his pony (who they fearfully mistake for a Black Rider at first) and they walk the rest of the way together. Hope you like it!
Obligatory hobbit music for you: [link]