Rick Astley – “When I Fall in Love”:
A Crooner’s Turn in a Synth-Pop World
When Rick Astley’s version of “When I Fall in Love” landed in November 1987 as a double A-side with “My Arms Keep Missing You,” it was a pretty surprising move. Here he was, at the absolute peak of his Stock Aitken Waterman (SAW)-fueled pop stardom—fresh off the global phenomenon of “Never Gonna Give You Up”—and what did he do? He put aside the drum machines and dancefloor grooves to cover a classic 1952 pop standard. And believe it or not, against all odds, it totally worked!
A Timeless Song in a Timely Voice
“When I Fall in Love” was originally made famous by Doris Day and later cemented as a classic by Nat King Cole. It’s the definition of a romantic standard: slow, delicate, and full of sincere emotion. Rick Astley’s version doesn’t try to reinvent it, and it doesn’t need to. His deep, velvety voice fits the song’s sweeping melody perfectly, offering a respectful, emotionally grounded performance that really proved he was more than just a pop puppet.
Instead of synth lines, you get lush string arrangements, and club beats are replaced with rich, warm production. This track truly showed off Astley’s vocal control and his genuine love for classic soul and traditional pop music—influences that would become much more prominent in his career later on.
The Chart Story and Holiday Magic
The single hit the UK just before the 1987 holiday season, which was a smart move to try and snag that coveted Christmas No. 1 spot. While it didn’t quite get to the top (it peaked at No. 2), it sold incredibly well and became a genuine seasonal staple. Its double A-side partner, “My Arms Keep Missing You,” got all the love on pop radio, while “When I Fall in Love” found its home on easy-listening stations and holiday playlists.
A Music Video Full of Classic Charm
The video for “When I Fall in Love” is just as understated as the song itself. It’s a black-and-white throwback, featuring Astley performing in a classic studio setting, mixed with subtle romantic visuals. It was a stark contrast to the pastel-drenched, fast-cut videos dominating the late ’80s pop scene, but it fit the mood perfectly—clean, classy, and sincere.
Enduring Impact: A Pop Star with Pipes
While most people remember Rick Astley for his incredibly catchy dance-pop hits (and, of course, the internet’s rickrolling phenomenon), “When I Fall in Love” revealed a completely different side of him. It showed that underneath all that SAW production polish was a vocalist with serious range—someone capable of handling material far older and more delicate than most of his chart contemporaries.
Astley would continue to explore this more classic side of his talent in later years, covering standards and soul classics in his live shows and on future albums. But it all really started here, with a holiday-season gamble that paid off big time and reminded audiences that he had much more to offer than just synth-pop hooks and sharp suits.