Songfacts®:

• Matt Pryor said in our interview that the inspiration for this track stemmed from a phrase mentioned by his Get Up Kids band mate, James Dewees: "I've had that phrase; my friend, James Dewees, who plays keyboards in the Get Up Kids, said that one time. He was talking about somebody specifically, but I can't remember who it was at the time. But it's talking about how there's always people who are happiest when they're complaining about something, or can't ever stop and find the joy in anything - it's just always something. And so he said that, and I thought it was a good line. So I wrote it down on my phone (laughing) and it was there for a year. And I kept going, 'Oh, yeah, that's a good name for a song.'"
  
  Pryor added that the song took on a whole new meaning when he finally wrote it: "And then when I was finishing this record up, that was one of the last songs I wrote. And I wrote it more as a break-up song, so it wasn't really about what James had originally coined the term as. But it's not really self-reflection, because I think it's written to somebody. It's definitely taking stock of what's going on and realizing that sometimes you can get to a point where you're just like, 'Am I really even trying?' (laughing) 'Or am I just being miserable?'"
• Pryor told us he was particularly fond of this song's title: "It's kind of like a bad Country and Western title, too. Crying in my beer or something."
• "Unhappy is the Only Happy That You'll Ever Be" features on Matt Pryor's second solo album, May Day. Pryor told us the raw production of the album reflects his emotional state at the time of recording: "I mean, it's a home recording written and recorded by someone who was very, very frustrated and somewhat angry. So I think that it was better to convey that. I'm not going to get hung up on what kind of microphones and pre-amps we're using to make the record. I just wanted to be raw, and I wanted it to convey the feelings that I was having. And I think I did that."