Growing up in the 1980s, the Brothers Chaps were creating comic books, filming Super 8 movies and eventually toying with a video camera.

[7] The character debuted in the children's book The Homestar Runner Enters the Strongest Man in the World Contest, which was subsequently posted online as a series of images.

[12] Mike also provides intentionally poor imitations of his brother's voice work for the Powered by The Cheat cartoon series on the Homestar Runner website.

[13][14] They have directed several music videos, including "Heimdalsgate Like a Promethean Curse" by Of Montreal, "Experimental Film" (featuring the Homestar Runner characters, most notably Strong Sad) and "Figure Eight" by They Might Be Giants, "Brand of Skin" by Folk Implosion, and "LA Lindsay" by Y-O-U, the band who also collaborated with the brothers on Strong Bad Sings.

In 2017, the duo along with Robert Schneider and James Husband formed the Air-sea Dolphin project, which had two split singles with Honey Radar and the fictional band Sloshy from the Homestar Runner universe.