Name: Sherwood Bailey
Played By: Sherwood Bailey
Born: Relatives: Unnamed mother, Wheezer (stepbrother), Spud (brother/stepbrother/half-brother?), Echo (stepsister),
Clubs: Dickie's Fire Squad
First Short: Big Ears
Last Short: Hook And Ladder
Smug, bratty, devious and yet devoted to his mother, Sherwood may not have been a popular Rascal, but he is notable for his part in one of the tangles and inconsistencies in the haphazard continuity between the Little Rascals shorts. He is his mother's favorite, but he is not the favorite stepbrother for Wheezer Hutchins or his sister Echo who are stuck living with him. The conundrum in this situation is that Echo has always been seen as early as Pups Is Pups as the younger sister of Chubby Chaney, while Wheezer's older sister was actually Mary Ann as far back as The Spanking Age. To confuse things furthur, Wheezer's older (possible step) brother previously is Spud Janney in Bear Shooters; Sherwood definitely inherited the "Spud" nickname in his absence. When Wheezer and his sister are rescued by their mother's sister to live with their father, a tale told in various forms in The Spanking Age, Small Talk and Dogs Is Dogs, Wheezer goes on to clash with the older brother he is best known for tangling with: Jackie Cooper, leaving Sherwood alone with his harridan mother and his dog, Nero, who he'll protect at all costs even after Nero is caught killing the neighbor's chickens.
The only creative way of resolving all these shorts together without disturbing the events in the series would be if Spud Janney was the older brother of Sherwood whose mother was once married and then divorced from Wheezer's father; Echo merely a substitite for Mary Ann, but even that doesn't entirely mesh with the references in the series. (Truth be told, continuity between shorts was not important to the Our Gang writers. The Rascals often played new roles or had their family structures altered as the plot dictated.)
A few constant things are know about Sherwood. He attended Adams Street Grammar School at the same time as Breezy Brisbane and Stymie. In Readin' And Writin', his mother giving him a rather effeminate poem to read to the teacher, and he reads it a bit too willingly. She also dresses him in a prissy "Little Lord Fauntleroy" outfit in Dogs Is Dogs; one wonders if liking that outfit too much led to him switching clothes with Echo in Choo-Choo and not balking too much in playing a female character in Breezy's play on Uncle Tom's Cabin. Besides those incidents, he's also partial to playing hooky with the others and listening to the tall tales of the old sea captain in Shiver My Timbers out at the Greenpoint Shipyards. He witnesses Brisbane's attempts to get tossed from school and gets to attend a lavish lawn party in Free Eats. He's also a part of Dickie Moore's Junior Fire Department in Hook And Ladder, but his proudest moment was probably losing Wheezer as a brother after getting dropped into the well near his property and conned by Stymie into cooking breakfast for the kids.