Meaning of “Sailing” by Christopher Cross

Sailing is a song performed by American singer and songwriter Christopher Cross. The lyrics of the song are about sailing and the beauty and liberation that come with it. According to Cross, he wrote the song about the fond memories he had while spending the summers of his teenage years sailing in Texas with a very close friend of his. Speaking with the famous American radio and television personality Howard Stern, Cross said of those sailing trips with his friend during his teenage years as trips that brought him total liberation. According to him, those sailing trips were very important to him since they provided him with some sort of escape from all the troubles of life.


Facts about the song “Sailing”

  • The song was written solely by Christopher Cross. According to Cross, the entire writing process of the song took about two years.
  • The song was produced by American singer-songwriter and music producer Michael Omartian, who also sang backing vocals on the song.
  • The song was released on 15th June, 1980 as a single from Cross’ debut album Christopher Cross – an album which won the Grammy Award for Album of the Year in 1981.
  • Sailing is one of the most famous songs in the yacht rock genre.
  • Sailing is the most successful song of Cross’ musical career. The song not only peaked at the number 1 spot on the U.S. Billboard Hot 100 but also won Cross as many as three Grammy Awards in 1981, including the Grammy Awards for Record of the Year and Song of the Year.
  • While accepting his Grammy for the song in 1981, Cross said that despite the song being his favorite on the entire album, it almost wasn’t released as a single.
  • Since its release in 1980, the song has been covered by several artists including Barry Manilow , N’Sync, and Avant.
  • Cross considers the song one of the best songs he has written throughout his entire career.
  • American rapper Sean Combs (also known as Puff Daddy or Diddy) sampled this song in his 1999 track titled Best Friends.

6 Responses

  1. Chris says:

    I loved this song from the very first note and syllable! Close your eyes and you can feel like you are sailing! Beautiful

  2. Ani says:

    It’s a song of passion- whether for sailing or dance or anything else
    An inspirational lifelong song
    Thank you!

  3. Jane says:

    It speaks of a freedom to me. Freedom to escape things in this life.

  4. Anonymous says:

    To me it’s a song for when the sun is setting. Not just for water but anywhere you can see it! Relax

  5. Anonymous says:

    It NEVER gets old, a timeless song that connects with your inner being, bringing you peace and escape. And the emotive vocals combined with the lyrics make it an unforgettable listening experience.

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