Bobby Caldwell Popular Song Rankings [2025]
Bobby Caldwell is one of the singers who represented the popular AOR genre from the 1970s to the 1980s.
Since 1980, he has been extremely popular here in Japan, and people of that generation may find him very nostalgic.
Here is a ranking of Bobby Caldwell’s popular songs.
Bobby Caldwell Popular Song Rankings [2025]
What You Won’t Do for LoveBobby Caldwell1rank/position

Bobby Caldwell is one of the singers who represents AOR and blue-eyed soul.
Although he was white, he gained popularity with an authentic R&B sound.
Among his works, this song is surely the timeless classic that continues to shine.
Its straightforward and passionate message—doing anything for the one you love—really strikes a chord.
The smooth melody and distinctive horn section create a sophisticated, romantic mood.
Released as a single from his debut album “Bobby Caldwell” in September 1978, it’s also famous for the anecdote that it was written in just two days.
I think it’s a perfect song for a leisurely holiday atmosphere.
Stay With MeBobby Caldwell2rank/position

It was the commercial song for the now-unseen cigarette ad, Parliament.
The singer was Bobby Caldwell, “Mr.
AOR.” Perhaps thanks in part to this commercial, he was extremely popular in Japan.
The ad featured flowing city nightscapes that matched the song perfectly, making it a cool commercial with a sophisticated, adult vibe.
Peter Cetera of Chicago also covered the song.
Heart Of MineBobby Caldwell3rank/position

The so-called AOR sound, with its urban, mature flavor, feels like a perfect match for that sentimental mood that tends to come at summer’s end.
Bobby Caldwell, a quintessential AOR singer-songwriter, is the embodiment of that vibe in both his sound and his voice.
His popularity is exceptionally high not only in his home country, the United States, but also here in Japan—so much so that he’s sometimes called the “King of AOR.” Here, I’d like to introduce the title track from Heart Of Mine, which Bobby released in 1989 and which became a hit.
His soulful yet refined vocals and the calm, polished arrangement are ideal for enjoying while driving along the coast at the end of summer.
It’s also a self-cover of a song he provided to another AOR luminary, Boz Scaggs, so be sure to enjoy comparing the two versions!
Silhouette of the WindBobby Caldwell4rank/position

As an AOR artist, Bobby Caldwell is by far the most well-known in Japan.
This piece is his debut song and is also widely known as one of his signature works.
His smooth vocals have a charm that makes the Japanese title “Silhouette of the Wind” feel like a perfect fit.
Released in 1978.
Sunny HillsBobby Caldwell5rank/position

Included on the 1982 album “Carry On.” Born in 1951, a singer from New York State.
With a medium-tempo, gently unfolding rhythm and a melancholic melody, his soulful vocals make this a song that truly resonates with the heart.
Baby, It’s Cold OutsideVanessa Williams & Bobby Caldwell6rank/position

Vanessa Williams and Bobby Caldwell have covered the classic Christmas duet “Baby, It’s Cold Outside.” The original was written in 1944, and since it was featured in the 1949 film Neptune’s Daughter, it has been known as a hugely popular duet.
The playful back-and-forth between the man and woman is so pleasing to the ear.
In this version in particular, Vanessa’s and Bobby’s voices blend beautifully.
Come To MeBobby Caldwell7rank/position

Bobby Caldwell is a singer-songwriter from the United States.
He is one of the leading AOR singers, widely known and loved in Japan.
“Come to Me” is a track from his 1978 album Bobby Caldwell.
All of his works evoke the atmosphere of a city night, but I think this piece in particular strongly conveys that mood.





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