This Lousy with Sylvianbriar track was inspired by the American poet Sylvia Plath, who published a 1960 collection with the same title. Of Montreal mainman Kevin Barnes told Rolling Stone: "I had been reading a lot of her poetry when I was making this record, and she sort of haunted the album."
As well as referencing Plath's family, the song is also about the relatives of somebody in Barnes' life. It contains the rather mean lyric "Baby, your family, they are just losers." The frontman told Rolling Stone: "It's not really meant to be an insult. It's more of an observation. When you have people who have loser relatives or loser parents, they have to come to terms with that. It doesn't mean that you love them any less. Some people are just that way, and you have to deal with the repercussions of dealing with loser relatives."
Geffen Records made history on June 27, 1994 when Aerosmith's "Head First" became the first major label song made available for exclusive digital download. Download speeds at the time were so slow it took around 75 minutes to download the track.