Lyrically, the song dares the listener to be stupid in various ways; this mostly by advising the listener to do the opposite of common idioms (e.g. "let the bedbugs bite" or "put all your eggs in one basket"), with the occasional absurd non sequitur (e.g. "stick your head in the microwave and get yourself a tan").
In an interview on VH1's Behind the Music, Devo's Mark Mothersbaugh stated in reaction to the song that: "I was in shock. It was the most beautiful thing I had ever heard. He sort of re-sculpted that song into something else and... I hate him for it, basically."
The music video is, according to Yankovic, also a "style parody" of Devo's works:
Yankovic and his band wear the yellow radiation suits from Devo's cover of The Rolling Stones' "(I Can't Get No) Satisfaction" video throughout. Much of the performance segments of the video are modeled on the "Satisfaction" music video, including the man having a fit on a wallpapered wall and floor. This is a parody of dancer Craig Allen Rothwell, nicknamed "Spazz Attack," who was featured in Devo's video with his signature flip onto his back.
Segments of the video are reminiscent of several of Devo's other videos:
"Devo Corporate Anthem" – In one scene, the band is standing in the same pose as Devo.
"Jocko Homo" – In another segment, the band wears nylon stockings over their heads.
"Beautiful World" – There are also several scenes of black-and-white stock footage, directed by Al (wearing a different costume than in the rest of the video) in front of an Interocitor. In addition, "tell me, what did I say?" also resembles the line from this song.
"Time Out for Fun" – The scenes where they come together and sing the main chorus is similar to where Devo comes together in the music video for this song and sings their main chorus.
"Come Back Jonee" – In one scene, the elderly men dressed up in cowboy suits are reminiscent of the elderly men bowling in the "Come Back Jonee" video.
"The Day My Baby Gave Me a Surprize" – In this part the group is in front of very simple computer graphics.
"Freedom of Choice" – The use of stop-motion animation and computer graphics is also reminiscent of this Devo video. The use of Roman togas also comes from "Freedom of Choice," and at one point, a man must choose between a banana and an accordion - in Devo's original, it's a gun or a grenade.
"Whip It" – The guitarist is alone, wearing a cowboy outfit (although the guitarist wearing a cowboy outfit was from the music video to the theme from the movie Doctor Detroit, which Devo performed, it is likely a coincidence, as the set was based on the "Whip It" video). There are cowboys in the "Whip it" video as well.
"Love Without Anger" – The scene in which the lyrics "you can just give up the ship" is displayed in a screen, mimics the display of the lyrics "love without anger isn't love at all" in the Devo video.
In addition, the scene of moving Mr. Potato Heads is reminiscent of a sequence in a Devo video shown at the start of live performances in which Mr. Potato Head-like figures emulate a concert crowd. Likewise, the woman signing lyrics mirrors a portion of the same video.
The man with a pipe, smiling and watching television with a chainsaw near the beginning of the video is a very typical Devo-like image as well, juxtaposing violent, out of context or unexplained occurrences and objects with a 1950s-like "wholesome American" feel. This man is meant to be J. R. "Bob" Dobbs, Head of the Church of the SubGenius.
The video also includes a lot of bizarre imagery which, for the most part, is irrelevant to the lyrics, such as Yankovic's face emerging from a screen filled with tiny baby figurines (a nod to the similarly Devo-esque scene in the video of "Mexican Radio" from early 80's band - and friend of Devo's - Wall of Voodoo, when lead singer Stan Ridgway's face emerges from a bowl of cooked pinto beans).
The machine Yankovic controls during parts of the video is an interocitor from the film This Island Earth.
The tune somewhat resembles that of "Deep Sleep" and "Big Mess" from Devo's "Oh, No! It's Devo" album.
Al's line "Yes!" in a slightly altered voice is reminiscent of the "Yes!" from "Explosions" on the same album.
The descending synth line heard during the lines "Dare to be stupid!" is similar to the one used in "Deep Sleep."
The swim goggles Yankovic wears over his eyes resembles those of Devo vocalist Mark Mothersbaugh's in the "Satisfaction" and "Come Back Jonee" videos.
The song is played in The Transformers: The Movie as the theme of the Junkions, a group of robots living on the planet of Junk. Like the song, Junkion speech was littered with cultural and television references.
In celebration of the release of the 2007 Transformers movie, rapper MC chris did a cover of "Dare to Be Stupid" and released it on his Myspace for download.
In the TV series Transformers: Animated, Weird Al makes a guest appearance as a Transformer named Wreck-Gar (who was the leader of the Junkions in the original movie). Near the end of the episode, he exclaims "I am Wreck-Gar! I dare to be stupid!"