Songfacts®:

• During a live performance, Morissette told fans the story behind this song, which finds the rage-fueled "You Oughta Know" singer in the unfamiliar territory of a healthy relationship.
  
  "When relationships get healthier and healthier we somehow equate that with not being as passionate or as sexy," she explained. "I've kind of realized that it's actually sexier when there's less drama. It's been better, and I never thought that that would be the case because of the whole clingy, overly dependent roller coaster that often times seemed very passionate and very sexy. And when I wrote 'Head Over Feet' about this particular person it was the first time that I actually had a glimpse of what it would be like to be in love and have it be something that was inducing of the heart palpitations, yet at the same time I could spend a couple minutes and actually not think about that person. It was very new to me."
• In the mid-'90s, it was a common tactic for record labels to withhold singles for purchase in order to boost album sales, which meant songs like this one couldn't make the Hot 100 despite getting lots of airplay (Billboard changed the rule in December 1998 to make non-singles eligible for the tally). The strategy certainly worked for Jagged Little Pill, which sold more than 16 million copies in the US.
  
  "Head Over Feet" landed at #3 on the Airplay chart and was Morissette's first #1 on the Adult Top 40 (an adult-oriented alt-rock and mainstream pop format).
• Morissette wrote this with her producer, Glen Ballard, who was a great fit for her. Ballard's biggest success to this point was producing and co-writing the first Wilson Phillips album, which contained three #1 hits. Morissette sounds nothing like Wilson Phillips, but both artists were very young and looking for an experienced producer who would value their contributions. During their sessions, Ballard and Morissette would often talk for a few hours before starting to craft a song, which they typically finished late at night in his Los Angeles studio. Working this way, they recorded 20 songs in 20 days, with 12 of them forming Jagged Little Pill.
  
  Creating the album was only part of the battle: Alanis didn't have a record deal, so they were shopping it while they were recording it. They got lots of rejections before landing it with Maverick Records, Madonna's label.
• Speaking with Spotify, Morissette talked about the song. "It's very conversational and doesn't adhere to any structure," she said. "I had been attempting to write without consideration for rhyming for quite a long time, and a lot of people would just stop writing with me - they would physically leave the room. So for me, "Head Over Feet" was a way for me to say, "This is actually what was happening. This was a real relationship. This person was very kind to me and it was really odd because I'd only been attracted to people who were mean to me." It was odd to be working with and befriending people who were so preciously kind. That song is about the conflict of wanting to embrace these kind moments, but also there being a disparity between what I felt I deserved and versus how kindly I was being treated."
• Morissette plays a harmonica solo on this track. She and Ballard got a few harmonicas in different keys from a Guitar Center in Sherman Oaks, one of which she played on "Head Over Feet."
• Samantha Marie Ware and Billy Lewis Jr. sang this on Glee in the 2015 episode "Jagged Little Tapestry."