Following a worldwide tour in support of Ixnay on the Hombre (1997), the band commenced work on a new album in July 1998, with the recording sessions lasting for about two months.

After the unexpected success of Smash (1994), the Offspring were signed to Columbia Records in 1996, releasing the fourth studio album, Ixnay on the Hombre (1997).

Frontman Dexter Holland told Rolling Stone in August 1998, "I wanted to write a record that wasn't a radical departure from what we've done before.

"[13] While most songs are the regular punk rock the band popularized, others such as the Latino-influenced "Pretty Fly (for a White Guy)" and the psychedelic "Pay the Man" add variety, "so that there's enough in there so people don't get bored".

"[16] He detailed that Americana was not thought right away as a concept album and "this really cool social statement", though once the band recorded a few songs complaining about 1998 America, "then we realized we had a theme".

[16] A major source of inspiration was seeing the people in Holland's hometown of Huntington Beach, such as the "wiggers" who were mocked in "Pretty Fly (for a White Guy)".

Despite dealing with aimlessness and disillusionment, derived from how the generation that had just got to adulthood was having problems in getting jobs and sustaining themselves, Holland declared that "I didn't want it to be a record that made you feel hopeless.

"[19] Artist Frank Kozik was hired to do the artwork for the album, as Holland found that his concert tour posters "had all the connotations we associated with Americana: very glossy, innocent and 1950s, but with a twisted aspect.

"[16] Kozik, who had known the singer for a long time, was reluctant to work for the band due to the reception his fans would have, eventually demanding $75,000 to do the Americana illustrations.

The album's cover art features a blond boy with an orthopedic boot seated on a swing holding a sand flea.

[16] Some pressings of Americana are also enhanced CDs and contain the karaoke videos of "Staring at the Sun", "Pretty Fly (for a White Guy)" and "Why Don't You Get a Job?

Club critic Stephen Thompson called Americana "the unbearable result being the kind of stupidity that thinks it's clever", considering it "bad enough to create a backlash against not only pop-punk, but also novelty songs, guitars, smug thirtysomethings, and the human race.