"Head over Heels" is a song recorded by British band Tears for Fears for their second studio album Songs from the Big Chair (1985). The song was released by Mercury Records, as the album's fourth single – initially on 10 June 1985 in Germany and then on 14 June in the UK.^[4] It was the band's tenth single release in the United Kingdom and eighth top 40 hit in the region, peaking at number 12. In the United States, it was the third single from the album and continued the band's run of hits there, peaking at number three on the Billboard Hot 100 chart. A limited edition four-leaf-clover-shaped picture disc was issued for the single's release in the UK. The song was also an international success, reaching the top 40 in several countries.

Cash Box called it "another searching lyric and richly evocative melody."^[5]

"When in Love with a Blind Man" is a short song that served as the B-side to the "Head over Heels" single. It features bassist Curt Smith on vocals and features a synthesized shakuhachi flute, a popular musical motif for pop music in the 1980s.^{[citation needed]}

This song predates a track called "The Working Hour" from the Big Chair album. The motif is identical; it's something Ian [Stanley] came up with which I later put melody and lyrics to. It was recorded in the Wool Hall and was the B-side to "Head over Heels".

— Roland Orzabal^[6]

The music video for "Head over Heels", filmed in late May and into June 1985, was the fourth Tears for Fears clip directed by music video producer Nigel Dick. A lighthearted video in comparison to the band's other promos, it is centred on Roland Orzabal's attempts to get the attention of a librarian (Joan Densmore), while a variety of characters (many played by the rest of the band), including a chimpanzee wearing a Red Sox jersey, engage in shenanigans in the library. The final scene shows Orzabal and the librarian as an older married couple. The video was filmed at the Emmanuel College Library in Toronto, Canada.^[7]

An edited version of "Head over Heels" is featured in the 2001 film Donnie Darko.^[8]

Personnel are taken from original album credits and the UK CD liner notes.^[9][10]

• Roland Orzabal – lead vocals, guitar, keyboards
• Curt Smith – bass guitar, backing vocals
• Manny Elias – drums
• Ian Stanley – keyboards
• Andy David – grand piano
• Marilyn Davis – backing vocals
• Annie McCaig – backing vocals
• Sandy McLelland – backing vocals