The song was recorded during the 1996 sessions for Where Have All the Merrymakers Gone. According to drummer Evan Sult, the song was written as a response to the Seattle music scene of the 1990s and its effect on mainstream culture..
It was released as a single in July 1997. The song gained popularity after Sean Nelson gave a copy of the album to a KNDD DJ. Shortly after this, it was picked up by KROQ-FM. It then appeared at #38 on the BillboardHot 100 Airplay chart. A music video was produced to promote the single. The song is regarded as a power pop single by MTV and a post-grunge anthem by author Ericka Chickowski.PopMatters describes the single as "a hyper-literate alt-rock dissection of the stupidity of the modern age". Music journalist Rob Sheffield also considers the song as "nineties pop-punk rage at its loudest".
"Flagpole Sitta" was used as the theme song for the British sitcom Peep Show for the second series onwards. In 2008, Harvey Danger singer Sean Nelson stated that Peep Show is "...the only pop culture item the song has been associated with that feels like a kindred spirit to the original attitude of the lyric." In 2016, he said: "It’s a joy to be affiliated with something that’s so smart and so funny and so kind of rude and weird."Rolling Stone ranked the song the 25th best of the 1990s.