Songfacts®:

• This is about a Southern California drug addict who travels on the Interstate 5 highway to feed his addiction. Mann told Newsweek magazine that the song was inspired by a friend with a nasty amphetamine habit and a large wallet. "In this case, [he] was living in Los Angeles, going down to Orange County and talking doctors into prescribing him speed, because he was charming and had money. It's well and good to have a lot of money, but you can't really afford to have that much money, because it enables you to slowly kill yourself."
• This song and the rest of the album was produced by Mann's bass player Paul Bryan, who also helmed her 2006 holiday album One More Drifter in the Snow.
• Mann told Billboard magazine that on the album "there's no electric guitar at all, which you weirdly don't miss. It's kind of this all-keyboard situation, which is great. It's an interesting amalgamation of sounds."
• Dcist asked Mann if this album has a storyline. She replied: "No. With Smilers, the 'concept' is really just to have each song be as different as it wants to be, and not worry about any kind of through-line. The through-line is really just the vibe of the instrumentation and the production and the musicians. We recorded it pretty much live. We did some rehearsing to figure out what we wanted to do with arrangements and stuff. But aside from the string sections and horn sections that are on a couple of songs, we did it live in the studio. One or two takes."
• In the same interview with dcist, Mann explained the album title: "I got to the title this really weird, long way 'round. The first thing that made me think of it was, I'd read this article about some study somebody did about the kinds of images people respond to. Most people respond to human faces. But apparently, across cultural lines, everybody responds most positively to a smiling cartoon face. I though that was really funny, so of course I felt like, 'Well, I've got to have a smiling cartoon face on my record. Clearly!' But then that got me thinking about this newsgroup that existed a long time ago, when I first got a computer. Me and this friend of mine would go on a newsgroup called alt.bitter, and it was all people who were, like, bitter about stuff."