Songfacts®:

• Written by Roland Orzabal and Curt Smith of Tears For Fears, this song finds Orzabal going "head over heels" for a girl and pleading with her not to break his heart. The lyric is a combination of poetry and pathos that veers into dangerous territory at the end when he sings:
  
  It's hard to be a man when there's a gun in your hand
  Oh, I feel so...
  
  Any girl getting this missive would be wise to file a restraining order.
• "Head Over Heels" was the tenth UK single release from Tears for Fears, and it scored them their eighth UK Top 40 hit. It is one of five hit singles from their third album, Songs from the Big Chair.
• The album Songs from the Big Chair takes its name from the 1976 American TV drama series Sybil, in which the title character, suffering from psychiatric problems stemming from child abuse, seeks refuge in her therapist's "big chair." For those of you who missed it, Sybil was based on the controversial book about a woman who was supposed to have had 16 different personalities. The TV series was pretty much the campiest, most-over-the-top portrayal of mother-daughter dysfunction since Mommie Dearest. Orzabal and Smith stated that they based this title choice solely on the concept that the songs on the album were so varied, that they all had different personalities all their own.
• The song "Broken" precedes this song on the album, and is played both before and after this song in concerts, as it was originally composed as a segue into "Broken."
• There are two versions of this song out there. The shorter version ends on a cold stop. The longer version is known as the "preacher version" because it opens with Roland Orzabal reciting the lyrics from their song "I Believe" as if delivering a sermon.
• The video to "Head Over Heels" was directed by Nigel Dick, who would later direct Britney Spears in "Baby One More Time." Roland Orzabal gave Dick the concept, which was meeting a beautiful girl in the library and growing old with her. He also suggested many of the very random images, like the rabbi and the chimp. There's even an homage to the movie Ghostbusters in a scene where Orzabal pulls a card catalog drawer and the cards go flying.
  
  Ripe for parody, in 2008 a "literal" version appeared on YouTube with dubbed lyrics that poke fun at the video's visuals.
• The song featured in the 2001 movie Donnie Darko during a scene where a camera flies around the school. Director Richard Kelly said on the DVD commentary that the scene in which the tune was used was written and choreographed specifically with the song in mind.
  
  Other uses of the song include:
  
  Fringe ("Brown Betty" - 2010)
  Degrassi: The Next Generation ("Drop the World: Part 2" - 2011)
  Orphan Black ("Ipsa Scientia Potestas Est" - 2014)
  The Late Bloomer (2016)
  GLOW ("The Dusty Spur" - 2017)
• "Head Over Heels" made an appearance at the 2022 Super Bowl halftime show when the piano riff was incorporated into Mary J. Blige's performance of her hit "No More Drama."