Songfacts®:

• This melancholy song is a lyrical handbook for heartbreak: kiss, fall in love, break up, cry.
  
  The singer has repeated this pattern so often he feels like he's an expert in "The Crying Game."
• This song was written by Geoff Stephens, a British songwriter who soon after writing this song, discovered and produced Donovan.
• Boy George recorded this as the theme song to the 1992 film of the same name, starring Jaye Davidson as a transgender woman - a secret that is not revealed until the end of the film.
  
  Stephen Woolley, who produced the movie, suggested Boy George to sing the title song. Woolley had worked with the Pet Shop Boys on an earlier film called Scandal, and asked them to produce the soundtrack. Neil Tennant of the group loved how George did the title song - he thought the Culture Club frontman sounded like Roy Orbison on the track.
  
  This version was markedly different from the original, as Boy George sang it in a much higher register. George both looked and sounded like a female, which synched with the film's plot.
• Dave Berry fronted an R&B group called Dave Berry and the Cruisers in the early '60s, scoring minor UK hits with "Memphis Tennessee" (#19, 1963) and "My Baby Left Me" (#37, 1964). After leaving the Cruisers, he recorded "The Crying Game," which marked a change of style for Berry. "I thought the guitar part was great," he told Let It Rock magazine. "I've always been an easy, middle-of-the-road sort of person in what I like. I've never been a hard-liner in any sort of music so it wasn't difficult to do numbers like 'Crying Game.'"
  
  Berry scored two more #5 UK hits: "Little Things" (1965) and "Mama" (1966).
• The extremely prolific UK session guitarist Big Jim Sullivan played on this track, which marked the first time a wah wah pedal was used on a UK hit. He played a Gibson 345 with an L5 jazz neck on the track.
• Jimmy Page was a session guitarist when Dave Berry recorded this track, and is often credited with playing the solo. Page says he didn't play on "The Crying Game," but did play on the Dave Berry and the Cruisers song "My Baby Left Me."
• Boy George made #15 US and #22 UK with his version. With Culture Club, he had his last hit in 1986; in 1988 he made #40 US with "Live My Life," but he didn't return to the charts until "The Crying Game."
• In America, The original Dave Berry version was never a hit, as he wasn't able to extend his reach beyond the UK. Until the song was used in the movie, the best known version in America was by Brenda Lee, who took it to #97 in 1965.