Bobby Caldwell (August 15, 1951 – March 14, 2023) was born Robert Hunter Caldwell and was an American singer, songwriter, and musician.
Bobby Caldwell was born in Manhattan, but grew up in Miami, Florida. His mother sold real estate and one of her clients was reggae singer Bob Marley who became friends with Bobby. Growing up in Miami exposed Bobby Caldwell to a variety of music such as Haitian, Latin, reggae, and R&B, but he was particularly drawn to rock and roll, jazz, and rhythm and blues.
When he was 12, Bobby started playing piano and guitar.
Bobby Caldwell was a member of a Miami band called Katmandu who wrote much of their own material while also performing traditional standards. At 17, he worked with the band in Las Vegas before moving to Los Angeles.
Bobby got his first career break as a rhythm guitarist for the one and only Little Richard in the early 1970s, but Bobby Caldwell and his band eventually left Little Richard, and Caldwell went solo.
By 1977, he had spent six years in Los Angeles playing in different bar bands and trying to get a record deal, eventually signing with TK Records back in Miami in 1978.
After songs for his first album were recorded, executives told Bobby Caldwell that they enjoyed the album, but thought it was lacking a hit. Caldwell returned to the studio for two days and wrote “What You Won’t Do for Love”.
TK Records was mainly an R&B label popular among African American listeners and executives at the label wanted to conceal the fact that Caldwell was white, so they kept his face off the album cover for “Bobby Caldwell”. When he toured with Natalie Cole to support the album, most of the audience was black and many were surprised that Caldwell was white.
“What You Won’t Do for Love” from the album “Bobby Caldwell” reached the top ten on the Billboard magazine Hot 100, R&B and Adult Contemporary charts.
The song has since been covered, remade and sampled many times. It was covered by Go West, Phyllis Hyman, Roy Ayers, Michael Bolton, Boyz II Men and Snoh Aalegra and by Elliott Yamin during the fifth season of American Idol in 2006, it was also sampled by Tupac Shakur for his hit “Do for Love”.
Caldwell’s track “My Flame” was sampled for “Sky’s the Limit” by The Notorious B.I.G which was released in November 1997.
Bobby Caldwell’s debut album was followed by “Cat in the Hat” in 1980 and “Carry On” in 1982.
For the album “Carry On”, Caldwell played all the instruments, was the producer and helped with arranging and mixing.
In 1983, Bobby released “August Moon” only in Japan and it was eventually released in the United States in the 1990s.
After TK Records shut down Singer Boz Scaggs advised Bobby Caldwell to write songs for other musicians. Bobby Caldwell wrote “The Next Time I Fall”, which became a number 1 hit for Amy Grant and Peter Cetera in 1983, along with songs for many other artists including Boz Scaggs, Roy Ayers, Chicago, Natalie Cole, Neil Diamond, Roberta Flack, and Al Jarreau.
Bobby Caldwell was very popular in Japan, where he was nicknamed “Mister AOR” (AOR is short for “Adult Oriented Rock”). In 1992, Bobby received the award for Best Foreign Artist at the 34th Japan Record Awards.
On the album “Blue Condition” in 1996, Caldwell turned from R&B to recording big band arrangements of songs from the Great American Songbook, particularly those sung by Frank Sinatra. He also portrayed Frank Sinatra in tributes to the Rat Pack in Las Vegas.
Caldwell continued to sing standards on “Come Rain or Come Shine” in 1999, “The Consummate Bobby Caldwell” in 2010 and “After Dark” in 2014.
In 2015, Bobby collaborated with record producer Jack Splash on the album “Cool Uncle”.
The track “Open Your Eyes” from “Cat in the Hat” was sampled by J Dilla on Common’s “The Light” from his 2000 album “Like Water for Chocolate”, and was was also covered by John Legend and Dwele.
In 2019, Lil Nas X was sued for $25 million for using the song “Carry On”, from the album o”Carry On”, without permission in his own song of the same name from his 2018 mixtape Nasaratt.
Bobby Caldwell died at his home in New Jersey, on March 14, 2023 at the age of 71.
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