A while back, we put together our list of the 25 greatest Yacht Rock songs ever written. If you like breezy Lite FM fare and hairy dudes with floppy mustaches, you have to check it out.
We only bring it up because the #1 song on that list deserves a little more consideration. As we argued at the time, “Escape (The Pina Colada Song).” by Rupert Holmes is the single greatest Yacht Rock song of all time.
It has everything that you’re looking for in a Yacht Rock classic: casual infidelity, dune sex, funk-lite synth. It also includes the line—“I am into champagne”—which of course underscores the protagonist’s deep class and sophistication.
“The Pina Colada Song” isn’t just the #1 song on our Yacht Rock list. It was a chart-topper upon its release in late 1979. And it has been in constant cultural circulation since its inception–a mandatory piece in the arsenal of any self-respecting beach bar cover band, a standard soundscape for the cruise ship pool deck, a soft-rock radio programming staple.
So you can be forgiven for assuming that Rupert Holmes is a one-hit-wonder. Nothing he did ever came close to the success of “Escape”–a song about a cocktail that Rupert Holmes doesn’t actually like.
But Rupert has a pretty interesting backstory. To wit… that includes flirtations with cannibalism and Barbara Streisand.
Cannibalism and Barbara Streisand
American by heritage and British by birth, Rupert already had a long and varied resume as a singer, songwriter, composer, arranger, and bandleader long before the success of the “Pina Colada Song.”
In fact, he made his first chart entry with a pop-rock band from Scranton Wilkes-Barre called The Buoys. He also contributed piano to the recording of their breakout hit, “Timothy”. The sympathetic baroque pop portrayal of two miners forced to cannibalize their dead co-worker, “Timothy” succeeded both in generating controversy and peaking at #17 on the Billboard Hot 100 in 1971.
Holmes spent the next decade establishing himself as a songwriting force, composing hits for Dolly Parton, Wayne Newton, the Partridge Family, and most notably, Barbara Streisand. He collaborated with the last of these on numerous projects of both stage and studio, including the coolest tune on Streisand’s “A Star is Born” Soundtrack.
Here’s a sampling of his work as a singer and songwriter.
Don’t Bogart That Beverage
Holmes is also a two-time Tony Winner, television producer, novelist, and perhaps most amazingly, has been married to the same woman since 1969.
This fact is noteworthy considering the theme of Rupert’s most famous song. It’s either ironic or fitting that a man so successful at monogamy is best known for a song in which a bored husband attempts infidelity only to find out that his wife is equally bored with him.
The good news is that “The Pina Colada” song isn’t at all autobiographical. In fact, at the time of writing, Holmes had never even tasted a Pina Colada, and confirmed as recently as 2019 that he still doesn’t particularly care for the cocktail.
In fact, in the original lyric for the song, the refrain was about film icon Humphrey Bogart…that is, “if you like Humphrey Bogart, and getting caught in the rain.”
Oof.
Fortunately, it occurred to Holmes that you can’t drink Humphrey Bogart, much less serve him with a parasol, so he changed the lyric to reference the first exotic cocktail that he could think of.
50 Million Rupert Holmes Fans Can’t Be Wrong
“The Pina Colada Song” also represents an unusual phenomenon in pop music, one in which a song is essentially named by the fans. Rupert Holmes called the song “Escape.” But Lite FM radio listeners of the time were hungry for anything vaguely nautical or Caribbean. “Escape” pretended to be a bit of both.
Radio request lines lit up with callers who demanded to hear “The Pina Colada Song.”
Rupert conceded that the fans had a point, and that this was probably the correct title for the song. Holmes issued his biggest hit as “Escape (The Pina Colada Song)” on all future releases.
And it’s easy to see why Holmes gave a nod to those radio callers. Their enthusiasm pushed “The Pina Colada Song” to the top spot on the charts. In fact, “Escape” is the first song to peak at the top spot on the charts in two different decades. In spite of its tropical vibe, it was a actually a winter hit, reaching #1 in mid-December of 1979.
K.C. and the Sunshine Band knocked it from the top spot the next week with “Please Don’t Go”.
Rupert reclaimed the #1 spot in the second week of January, 1980.
Anyway, Rupert is widely credited with popularizing a drink that, reportedly, he still doesn’t like.
In case you missed it, here’s our Best of Yacht Rock playlist once again.