The cartoons are nominally centered on title character Homestar Runner. However, the series titled Strong Bad Email, in which another main character, Strong Bad, answers emails from viewers, is the most popular and prominent feature of the site. While Homestar and Strong Bad are the main characters, the site has grown to encompass dozens of other characters over the years.
The site is one of the most popular collections of Flash cartoons on the Internet and is notable for its refusal to sell advertising space (the creators pay for everything through merchandise sales, which includes a line of T-shirts). It grew in popularity largely through word of mouth.
Homestar Runner was brought to life in Atlanta in 1996 by two University of Georgia students, Mike Chapman and Craig Zobel, who were working summer jobs surrounding the 1996 Summer Olympics. On a day off, they visited a bookstore where they found that the state of children's books was dismal. Intending to parody this, they wrote the original story The Homestar Runner Enters the Strongest Man in the World Contest. This story featured Homestar Runner, Pom Pom, Strong Bad, The Cheat, and a few characters that are rarely seen in recent cartoons: The Robot, Mr. Bland, Señor, and the Grape Fairie. This hand-drawn book was the only incarnation of the characters for several years.
They later used Mario Paint, a Super Nintendo video game, to create the first cartoon of the series. By 1999, Mike and his younger brother Matt Chapman, who call themselves The Brothers Chaps, were learning Flash and looking for something on which to practice. Digging out the old children's book provided a solution. The site domain was registered on December 6, 1999, and around the start of the year 2000, homestarrunner.com was live. Matt provided the voices of the male characters, while Missy Palmer provided Marzipan's voice.
Regarding the origin of the name "Homestar Runner", Matt had this to say, from an interview with Kevin Scott:
It actually comes from a friend of ours. There was an old local grocery store commercial, and we live in Atlanta, and it advertised the Atlanta Braves. It was like, "the Atlanta Braves hit home runs, and you can hit a home run with savings here!" And so there was this player named Mark Lemke, and they said something like "All star second baseman for the Braves." And our friend knows nothing about sports, and so he would always do his old-timey radio impression of this guy, and not knowing any positions in baseball or whatever, he would just be like, "homestar runner for the Braves." And we were just like, "Homestar Runner? That’s the best thing we’ve ever heard!"
The site grew slowly at first, but by mid-2001 it began to take off with the first Strong Bad Email. The number of visitors to the site grew, and by March 2003 the site had outgrown its original web host, Yahoo!. Merchandise sales pay for all of the costs of running the website as well as living costs of the creators, whose retired parents managed many of the business aspects.
On January 30, 2006, Podstar Runner was launched, allowing people to download select Strong Bad Emails and other toon episodes to a video-enabled iPod. Once made available through iTunes' podcast directory, it very quickly took the #1 slot on Apple's "Most Popular" podcast list. Podstar Runner was taken down on September 21, 2007, for reasons unknown. A new version was introduced on Thursday, January 10, 2008.
The Brothers Chaps on occasion have partnered up with rock band They Might Be Giants and supplied animation for a music video of their song "Experimental Film. The creators of Homestar Runner spent a day with the band, and those songs have found their way onto the website in the form of "Puppet Jam," a subset of "Puppet Stuff," where Puppet Homestar rocks out with TMBG. TMBG also wrote the music for Strong Bad Email #99, "Different Town." Also, on the 200th strong bad email, They Might Be Giants wrote and vocalized the beginning song. Another group, The Skate Party, helped The Brothers Chaps create "The Cheat Theme Song. As well, a band named Y-O-U helped with the Strong Bad Sings and Other Type Hits CD, as well as on the strongbad email.exe DVDs.
The Brothers Chaps also employed the services of the erstwhile acapella band DaVinci's Notebook to create a theme song for the old-timey version of The Cheat, called "Ballad of The Sneak".
A review published in National Review characterized the site's humor as having "the innocence of slapstick with sharp satire of American popular culture" — humor that "tends to be cultural, not political."
Other main characters include Marzipan, Homestar's sometime girlfriend and the only female main character on the site; Pom Pom, Homestar's best friend; Strong Sad, Strong Bad's perpetually depressed younger brother; Bubs, the local concession stand owner; Coach Z, a coach with many problems; the King of Town, the assumed ruler of Free Country, USA; and his loyal servant The Poopsmith. Rounding out the cast is Homsar, an enigmatic and confusing character introduced due to a misspelling of Homestar in a Strong Bad Email.
Some cartoons take place in an old-time setting, with most of the Homestar Runner characters having direct counterparts in the Old-Timey cartoons. These cartoons are in black and white with a film grain effect added and scratchy audio quality. They parody the distinctive style of animated cartoons during the 1920s and 1930s, and can be seen as perhaps purposely unfunny, to make a slanted joke about such old-style cartoons.
"Powered by The Cheat" are cartoons created by the same named character, which feature the main characters, but with an amateurish style of animation, nonsensical plots and bad voice acting.
Another series of cartoons, Stinkoman K 20X6 (abbreviated to 20X6; pronounced "Twenty Exty-Six"), originated from a response to an email asking Strong Bad what he would look like if he were an anime character. The main character, Stinkoman, is an anime version of Strong Bad with blue hair, a shiny body and robot boots. He is always looking for a fight, asking various characters he interacts with to engage him in a "challenge". The characters in 20X6 cartoons each have a counterpart in the Homestar Runner universe and their features are based on common anime and Japanese video game stereotypes.
Other cartoons introduce completely new casts of characters. Limozeen, an 80s glam metal band was depicted in a cartoon that described a short-lived Saturday morning cartoon entitled Limozeen: But They're in Space!. Sweet Cuppin' Cakes is a surreal children's cartoon also introduced in a Strong Bad Email, featuring characters like "Eh! Steve!" and The Worm. The Cheat Commandos is a parody of G.I. Joe that created a cast of characters that are the same species as The Cheat.
A very important note; Coach Z's mispronunciation of the Cheat's name as "the Chort" actually was confirmed to be a nickname combining short, and cohort.
Several episodes have been dedicated to special days of the year. For example, every Halloween, a cartoon is released that features all the characters in costumes celebrating some traditional aspect of Halloween (such as ghost stories, trick-or-treating or pumpkin carving). The characters' costumes are often famously esoteric, full of obscure pop culture references or characters from movies and television shows made in the 70s, 80s and 90s; for example: Prince, Jambi the Genie, Flavor Flav, Walter Sobchak, a Sleestak and Angus Young. April Fool's Day features various gags, such as turning the site into a "PAY PLUS!" offer site or flipping it upside down. The characters also celebrate an annual holiday called "Decemberween", a parody of Christmas that features gift-giving, carol-singing and decorated trees. The fact that it takes place on December 25, the same day as Christmas, has been presented as just a coincidence, and it's been stated that Decemberween traditionally takes place "55 days after Halloween".
Other holidays celebrated include New Year's Day, "The Big Game" (around the time of the Super Bowl), St. Valentine's Day, Mother's Day, "Senorial Day" (a reference to Senor Cardgage and Memorial Day), Flag Day, Independence Day (which Homestar calls "Happy Fireworks"), Labor Day (occasionally referred to as "Labor Dabor"), Thanksgiving and, most recently, Easter.
Arguably their most famous game, "Peasant's Quest", is an adventure game featuring Rather Dashing, a young peasant in short pants. He vows to kill the destroyer of his cottage: Trogdor the Burninator, a dragon created as a result of yet another sbemail. The game uses a system that is a near replica of Sierra Entertainment's Adventure Game Interpreter, used in King's Quest, Space Quest and several other early Sierra titles. Recently, the website has produced Wii versions of some of the games on the site, for the Wii browser. When played on the computer, these use the mouse only.
On April 10, 2008, a new episodic game called Strong Bad's Cool Game for Attractive People was announced for the Wii's WiiWare service and Microsoft Windows, developed by Telltale Games in partnership with Videlectrix. The first episode Homestar Ruiner premiered on August 11, 2008 worldwide for Windows on Telltale Game's website and in North America on Nintendo's WiiWare service on August 11, 2008. It was also released in Europe and Australia the following Friday (August 15, 2008). The second episode, Strong Badia the Free, was released on September 15th on the Telltale Game's website and on the WiiWare service in North America. The game currently has no European release date. Episode three, titled Baddest Of The Bands, was announced by Telltale games as part of a trailer in the second game.