|Alias||*Greg (by Wirt) 
|Status||Alive; Inactive in The Unknown|
|Role||Deuteragonist, Younger Sibling|
|First Appearance | Cast|
|Cartoon Debut||Chapter 1: The Old Grist Mill|
|Comic Debut||OTGW Comic Book 2015 Issue #1|
|English VA||Collin Dean|
|International VA||Matheus Calliano (Brazil)|
Did you know if you soak a raisin in grape juice it turns into a grape? It's a Rock Fact.
— Greg to Wirt, The Old Grist Mill.
Gregory, affectionately nicknamed Greg, is Wirt's younger half-brother. He is a very energetic boy who always has a smile on his face and very wild ideas on his mind. He's endlessly fascinated by everything, including things that would normally seem scary such as the ghost in Mad Love. He has a habit of wandering out on his own. He has a pet frog, which he found before his descent into the Unknown. He gives it a different name every chapter (Kitty, Doctor, George Washington, etc) but ends up naming it Jason Funderburker in Chapter 10. He also carries a rock (that was stolen from Mrs. Daniel's garden), that will randomly make Rock Facts. He is the deuteragonist of the show.
He is voiced by Collin Dean.
Over the Garden Wall:
Gregory sounds and appears to be very young. He is very small and plump, compared to other characters. He wears a white shirt with a small brown ribbon, light green overalls with round black buttons, and black shoes with high white socks. He also has a brown satchel and wears a tin tea kettle on his head. Greg's hair is also much neater when compared to his brother's, before their descent into the Dark Forest.
Tome of the Unknown Concept:
From Gregory's creation during the pre-production of Tome of the Unknown in 2006, Gregory has gone through several changes in his appearance. For his concept in the Pilot Episode, and eventually in Over the Garden Wall miniseries, Gregory's Halloween costume most prominently goes through several changes.
As shown in the sketch on the left, Greg's character design remained consistent with keeping his height relatively low, right at Wirt's hip (although cut off from the sketch's top left corner). Greg's eyes are always drawn round, large, and he is always drawn with a button-like nose. In the Art Book, we are shown sketches of potential Halloween costumes for Greg. One of the sketches depicts Greg's earlier concept of a sailor. We see this sailor design carried over, and although it did not make it onto Greg's final design it was referenced in Chapter 1: the Old Grist Mill, by two boys dressed as sailors playing with a toy boat in this episode. McHale explains that due to Greg resembling Flap Jack, from Cartoon Network's other program, The Marvelous Misadventures of Flapjack, that his design was changed. (Sketch 1 in infobox tab.*)
In another sketch Greg is shown wearing a military ensemble: a tall shako (military hat), sword at his side, and pants tucked into his boots. Other sketches keep his overalls, with some minor variations of a bow tie instead of suspenders, but exchange Greg's Tea Kettle for a pot, mushroom, and kettle. McHale notes that the sketch for Greg in the pumpkin suit was inspired from his own childhood where he also wore a pumpkin suit.
Differences Between Tome and OTGW:
Gregory's appearance overall is the same. He wears the same Halloween costume and silver Tea Kettle. However, at different angles Greg's overall pant hem's can seem larger or slimmer than they normally appear to be in Over the Garden Wall. Unlike Wirt, who has a distinct facial difference in the pilot episode, Greg does not.
Greg is the happy-go-lucky optimist of the trio, often remaining positive and unconcerned even in the face of danger and impossible odds. This is likely due to the fact that being so young, Greg is incapable of grasping the true nature of his and his brother’s situation and instead views everything that happens to them with a light-hearted innocence. His outlook remains unaffected even as the Beast tries to tempt him into despair. He’s a free spirit and is content marching to the beat of his own drum, showing little inhibition when it comes to expressing himself and often getting sidetracked/wandering away from the group whenever it suits him. Greg wholeheartedly believes that he can do anything when he sets his mind to it, and he refuses to give up in even the bleakest of situations.
Despite his naivete, Greg is quite intelligent. Examples of this include how he quickly deduces that Wirt wanted to ask out Sara and that it was Sara in the bee costume, he formulates the plan to have the benefit concert for the animal school, and even manages to trick the Beast into taking him instead of Wirt, not giving in to the Beast's hopelessness, as his optimism is nearly boundless.
Greg’s optimism isn’t easily shaken by Wirt’s dour outlook— in fact, he seems to take everything his brother says quite literally, and tends to puts a positive spin on Wirt’s negativity rather than be deterred by it. Despite often seeming annoying to his brother, Greg loves Wirt and genuinely wants what's best for his brother and encourages him to ask Sara out and try to express himself more. He remains unaffected by his experiences in The Unknown even after their journey has ended, and happily recounts the tale as if it were a grand adventure.
- Gregory is an animal lover, given his friendly interaction with his frog, the dog, and black turtles, and he dresses up as an elephant (sort of) for Halloween.
- Greg and his father have both suggested to Wirt that he join the high school's marching band.
- Greg's Halloween costume is an elephant.
- Like Wirt, Greg seems to possess some creative talent, his impromptu outbursts of song and ability to compose lyrics off the top of his head not unlike his brother's poetic musings.
- Greg was shown knowing how to play the trumpet in Chapter 8, Babes in the Wood.
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