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. His major physical characteristic is his short dark hair, usually worn in a crew cut. 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, he was one of the strip's primary figures in its first few years. He was mainly utilized as a "straight man" for Charlie Brown, but would soon be eclipsed by the newer and more developed characters, such as Linus and Lucy. His disappearance from the strip was even faster and more complete than those of the other early characters, Patty and Violet; as early as the late 1950s, his appearances became noticeably rare.
In the 1965 animated TV special A Charlie Brown Christmas, Shermy has only 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." The only television special in which Shermy is a main character is Charlie Brown's All-Stars which first aired in 1966. Shermy has more that thirty lines of dialogue in that special, in which he appears as the best player on Charlie Brown's baseball team, after Snoopy.
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 looked remarkably like him appeared on November 9, 1975. Schulz said he had no regrets about dropping Shermy from the cast, and stated many years later that it had gotten to the point by then 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 is also mentioned briefly in the musical You're a Good Man, Charlie Brown, in the song "The Doctor Is In".
- Shermy is one of the many Peanut characters to appear in the video game Snoopy's Street Fair, in which, he owns a root beer booth.