Songfacts®:

• This piano ballad from Tori Amos' second solo album finds her comforting a man who has given up on himself. It was inspired by a letter she received from a fan. She told The Baltimore Sun in 1994:
  
  "It was a picture of - he had drawn himself. It was a pencil drawing. Greg has kind of scrawny hair and glasses, and he's very skinny and he held this great big flower. Greg is 23, lives in the north of England, and his life is over, in his mind. I found this a reoccurrence in every country that I went. In that early 20 age, with so many of the guys - more than the girls, they were a bit more, 'Ah, things are just beginning to happen.' The guys, it was finished. The best parts of their life were done. The tragedy of that for me, just seeing that over and over again, got to me so much that I wrote 'Pretty Good Year.' You don't really know what my role is. Am I Lucy, or am I that eight bars of grunge that comes out near the end where I express, and then nothing, everything else is Greg's story? I found that kind of really fun. The emotion is coming from somebody else's story. And yet it touched me so that I could sing it."
• In a 1994 Creem interview, Amos explained how the tune relates to her Little Earthquakes track "Winter." She said: "On 'Winter,' the father sang to me, 'When you gonna make up your mind? When you gonna love you as much as I do?' and in 'Pretty Good Year' on the new album, I sing to the boyfriend, 'What's it gonna take till my baby's alright?' There's no self pity in the song and yet it's a tragedy. It's a tragedy because I can't make him love himself. I can't do it. No matter how much I beat it into him, I can't do it for him. Funny how the tables have turned isn't it?"
• This was one of two singles from the album to reach the Top 10 in the UK. The other was "Cornflake Girl," which peaked at #4.
• This wasn't released as a single in North America.
• 1994 was a pretty good year for Amos. Under The Pink debuted at #1 in the UK and boosted her growing popularity in the US, where it peaked at #12 on the albums chart.
• The lyrics mention how Greg likes to burn CDs. By the time this song was released, CDs were starting to outsell cassettes and some folks even started using CD-R disc burners to make copies of albums or their own mixes, although the practice didn't really take off until the 2000s when CD-R burners dropped in price. But the lyric has a dual meaning. "People were beginning to burn CDs at the time, but my other self is an arsonist," Tori wrote in the liner tones to the 2015 deluxe edition of the album. "I love fire. In another life I'd be one of those pyrotechnic lesbians on some movie set. So when I'm singing about burning CDs, I'm there with a blowtorch really burning the f--kers. Some people thought I was being forward thinking with that lyric, but there's a side to me that's saying, 'Oh no, honey, I'm much more primitive than that.' I'm like Lucy, the prehistoric thing that those scientists dug up that was millions of years old - they might have been playing 'Lucy in the Sky With Diamonds' when they found her - I'm talking about fire."
• The music video reunited Tori with her Little Earthquakes director Cindy Palmano, who recreated the minimalist aesthetic of the earlier clips. In the video, Tori launches through a window into a white room where she lounges in a chair and grooves with underwear-clad dancers.
• This was used on the TV show Casual in the 2017 episode "99."
• A cleaning mishap temporarily cost Amos her voice during the making of the album, and her self-pity over the incident made its way into this track. "I was spraying Pledge polish in a cupboard and I inhaled it and I got a lung infection which meant I couldn't speak, or sing, for three weeks," she recalled in a 1994 Hot Press interview. "And I really thought my voice was damaged forever and had to do voice lessons on the phone, with this voice teacher to try and get the natural cortisone back on the cords. I was thinking, 'What if I never sing again?' Then I'd say, 'If I can't sing what's the point in being alive, is this person worth anything at all?' And there were moments where the only answer to that question was 'no.' Then I'd give in to the self-pity that comes out in the song 'Pretty Good Year,' and in the lyric 'They say you were something in those formative years.'"