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Shermy began as one of the strip's main characters, being one of only three child characters who appeared in Peanuts when it started publication in October 1950. However, his personality was never very strongly developed and, as more characters were introduced to the strip, Shermy's appearances became much less frequent. By the time that the comic strip was first adapted for television in 1965, Shermy had already faded into relative obscurity and he ceased to appear in the strip four years later.
In the early years of the strip
Shermy was one of the three earliest characters to appear the strip, appearing in the very first strip on October 2, 1950. However, he was not given a name until December 18, 1950. In the early years of the strip, there were hints that he had a relationship with Patty. In his appearances in the strip, Shermy is often portrayed as Charlie Brown's superior at things that matter to Charlie Brown, especially athletics. Though he speaks the only line of dialogue in the first strip and was one of the strip's primary figures in its first few years, he was mainly utilized as a "straight man" for Charlie Brown. Shermy was sometimes said to play the position of first base on Charlie Brown's baseball team.
Gradual disappearance from the strip
Shermy's disappearance from the strip was even faster and more complete than those of the other early characters, Patty and Violet. As early as late 1952, his appearances were becoming noticeably rare because of the popularity of the newly introduced characters Lucy and Linus.
By 1969, Shermy had pretty much disappeared from the comic strip. His last official appearance is considered to be June 15, 1969, although a character who looks remarkably similar to him appears in the strip from November 9, 1975. Schulz said that he had no regrets about dropping Shermy from the cast. He stated, many years later, that it had gotten to a point where he only used Shermy in situations where he "needed a character with very little personality".
Shermy is referred to by name in the strip from March 13, 1977, in which Charlie Brown and Lucy are discussing players on their baseball team. He is referred to as the team's designated hitter, although in his days as a Peanuts regular (which predated the creation of the DH position) he usually played first base.
Shermy's major physical characteristic is his short, dark hair, which he had styled in a crew cut on April 18, 1953, and kept that way permanently thereafter. Shermy sometimes makes reference to the fact he seems doomed to have that look; he complains to Charlie Brown that he got a new hairstyle one weekend only to shortly come down with an illness that kept him from attending school. By the time the illness subsided, Shermy's hair had returned to its normal look, to which Shermy exclaims "I wasted a good haircut!" in not getting to model it at school. Apparently Schulz himself was not a big fan of this look, even though he never changed it, as he once commented that he "disliked" the way he drew Shermy's hair.
In other media
Shermy appears in multiple Peanuts television specials (although he becomes more of a rare character after the 1960s), beginning with A Charlie Brown Christmas in 1965, where he has one line of dialogue. Upon being cast as a shepherd in the gang's Christmas pageant, he laments, "Every Christmas it's the same: I always end up playing a shepherd." His appearances also include (sometimes with dialogue and sometimes without) Charlie Brown's All-Stars, It's the Great Pumpkin, Charlie Brown, You're in Love, Charlie Brown, It Was a Short Summer, Charlie Brown, You're Not Elected, Charlie Brown, Be My Valentine, Charlie Brown, It's Your First Kiss, Charlie Brown, Is This Goodbye, Charlie Brown?, Why, Charlie Brown, Why?, It's Spring Training, Charlie Brown, It Was My Best Birthday Ever, Charlie Brown, and I Want a Dog for Christmas, Charlie Brown with many of the latter being produced several years after he had already disappeared from the comic strip. Shermy is mentioned briefly in the musical You're a Good Man, Charlie Brown, in the song "The Doctor Is In", but does not appear or have a speaking part; and he also makes appearances in three feature films including A Boy Named Charlie Brown, as well as a cameo appearance in Snoopy Come Home. Shermy is also seen several times in The Charlie Brown and Snoopy Show and is even mentioned by name in Episode 13 from television (as seen on the "Go Snoopy Go!" DVD).
Shermy returned to the animated specials in the 2011 Direct-to-DVD Happiness is a Warm Blanket, Charlie Brown, which includes a scene based on the very first Peanuts strip, where Shermy notes how much he hates Charlie Brown. He also plays a supporting role in the 2015 computer-animated film The Peanuts Movie, where his last name is revealed to be "Plepler". It is also shown in the same movie that he has a younger sister, though this is not considered canonical.
Shermy's TV and film appearances
- A Charlie Brown Christmas (1965)
- Charlie Brown's All-Stars (1966)
- It's the Great Pumpkin, Charlie Brown (1966)
- You're in Love, Charlie Brown (1967) [silent]
- It Was a Short Summer, Charlie Brown (1969)
- A Boy Named Charlie Brown (1969) [silent]
- Snoopy, Come Home (1972) [silent]
- You're Not Elected, Charlie Brown (1972) [silent]
- Be My Valentine, Charlie Brown (1975) [silent]
- It's Your First Kiss, Charlie Brown (1977) [silent]
- Is This Goodbye, Charlie Brown? (1983) [silent]
- The Charlie Brown and Snoopy Show (1983-1986)
- Why, Charlie Brown, Why? (1990) [silent]
- It's Spring Training, Charlie Brown (1996) [silent]
- It Was My Best Birthday Ever, Charlie Brown (1997) [silent]
- I Want a Dog for Christmas, Charlie Brown (2003) [silent]
- Happiness is a Warm Blanket, Charlie Brown (2011)
- The Peanuts Movie (2015)
- Along with many other Peanuts characters, Shermy appears in the video game Snoopy's Street Fair, in which, he owns a root beer booth.